14 Outdoor Things to do in Chicago This Summer

– By Tom Schaffner

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Cold and icy weather generally forces residents and visitors to deal with two distinct Chicago seasons — the “indoor season” and the “outdoor season.”  Not surprisingly, the indoor season closely aligns with the fall and winter months (October through March) and the outdoor season closely matches the spring and summer months (April through September).

A list of indoor activities in Chicago usually includes museums, sporting events (such as hockey or basketball), visiting interesting taverns and restaurants, shopping excursions, bowling lanes, indoor gardens and conservatories, gyms & fitness facilities, and much more.  The outdoor season means warmer weather and endless opportunities for unique activities and outdoor things to do in Chicago.

In 2021, as Chicago slowly reopens after more than 12 months of quarantines and social distancing, residents and visitors alike are rediscovering the city during the outdoor season.  We’ve put together a list of outdoor activities for residents and visitors who are looking for a way to put a little fun back into their lives while the weather and the pandemic allow them to do so:

Outdoor Things to do in Chicago

  1. Lincoln Park Zoo
  2. Take in a Ball Game
  3. The Lakefront Trail
  4. Kayak the Chicago River
  5. Japanese Garden
  6. Visit a Cemetery
  7. The 606
  8. Public Art in the Loop
  9. Art on the Mart
  10. Charter a Boat
  11. Chess Pavilion
  12. Chicago Riverwalk
  13. Beaches
  14. Navy Pier

1. Lincoln Park Zoo

Although the Lincoln Park Zoo is open 365 days a year, there’s always more to see and do during the warmer weather than during the harsh winter months. Founded in 1868, the Lincoln Park Zoo is the fourth oldest zoo in the nation and, like other zoos, allows visitors to view the animals in areas that replicate their natural habitats. If you’re looking for outdoor things to do in Chicago that involve roaming around beautiful landscaping with manicured lawns and scenic gardens all throughout a 35-acre site, then The Zoo should be at the top of your list. It is located in the heart of the Lincoln Park neighborhood. Admission is free, although in 2021 you need a reservation in order to enter the zoo.

2. Take in a Ball Game

Warmer weather means baseball and this year, both the Cubs and the White Sox are welcoming fans back to the ballpark with appropriate pandemic safeguards in place.  Although season ticket holders have top priority for the first available seats, many seats at most games are available to the general public on a first-come, first-served basis and can be purchased online.  I don’t know about you, but hearing the crack of the bat with a beer in one hand and a hot dog in the other seems awfully “normal” to me.

outdoor things to do in chicago - take in a ball game

3. The Lakefront Trail

Walk, run, bike, or rollerblade Chicago’s magnificent Lakefront Trail, which stretches for 18 wonderfully scenic miles and offers a variety of outdoor things to do in Chicago all in one place. Along the way, you’ll pass parks, the Museum Campus, Soldier Field, McCormick Place, many views and perspectives of Chicago’s skyline, the South Shore Cultural Center, and many more sites and attractions.  Because there is so much to see and do on the Lakefront Trail, many locals insist that traveling this unique path is like taking a “stay-cation” in Chicago.

4. Kayak the Chicago River

Natives and early explorers of Chicago traveled by canoe on the North and South Branches of the Chicago River to reach what would later be called Lake Michigan. You can do the same at various locations along the River with guided tours that depart during all hours of the day, for nighttime sails, and even trips that are timed to coincide with special events that take place in the city, such as the weekly fireworks show at Navy Pier.

Outdoor things to do in chicago - kayak the chicago river

5. Japanese Garden

Located in Jackson Park just south of the Museum of Science and Industry is a Japanese garden sometimes referred to as the “Garden of the Phoenix” or the “Osaka Garden,” (Osaka is a sister city of Chicago).  The garden was a gift to Chicago from Japan in honor of the World’s Columbian Exposition (1893) which was held in Jackson Park.  The blossoming of the cherry trees in spring is an annual highlight of the park, however, the entire garden is beautifully landscaped, and located on a secluded island in the park.

6. Visit a Cemetery

This might not be on everyone’s list of outdoor things to do in Chicago, however, cemeteries are quiet, peaceful, landscaped, and are the final resting spot for notable Chicagoans, many of who have beautiful gravestones and mausoleums that adorn their tombs. On the North Side, visit Graceland Cemetery where Daniel Burnham, Ernie Banks, Roger Ebert, Marshall Field, William Le Baron Jenney, Joseph Medill, Ludwig Mies Van der Rohe, Ruth Page, George Pullman, and many other famous people are buried.  On the South Side, visit Oak Woods Cemetery, the final resting spot for Cap Anson, Enrico Fermi, John H. Johnson, Jesse Owens, William Hale Thompson, Harold Washington, Ida B. Wells, and Bill Veeck.

7. The 606

The 606 is an abandoned 2.5-mile railroad line that has been converted into an elevated trail/park that runs parallel to North Ave. on the north side of the city from Ashland Ave. on the east to Ridgeway Ave. on the west.  Perfect for joggers, walkers and bikers, the trail is clean, well-maintained and also has a number of interesting bars, restaurants and shops that can be visited along the way.  The trail takes its numeric name from the first three digits of all Chicago zip codes.

8. Public Art in the Loop

Chicago’s Loop is a veritable gallery of public art featuring works from some of the most famous artists in the world, including Picasso, Calder, Miro, Dubuffet, Chagall, and many more.  The most notable (and famous) works are all within a short walk of one another and can easily be found online.

9. Art on the Mart

This innovative digital presentation uses the broad front face of the Merchandise Mart (the side of the building that faces the Chicago River) as a screen to display projected art in nightly “programs” that begin at 8:30 p.m. and 9 p.m.  Best spot to view the presentation is from the south bank of the Chicago Riverwalk between Wells and Lake Streets. For those looking for outdoor things to do in Chicago that are truly unique to our city, then this should be on your list!

10. Charter a Boat

There’s an awfully big body of water located on Chicago’s eastern border — why not charter a boat and do some sightseeing, fishing, sun-worshipping or celebrate a special occasion (and let the crew do all of the work)?  There are plenty of charter boats in the Chicago area, your next trip is only a few clicks away on your smartphone.

11. Chess Pavilion

If you enjoy playing chess — or enjoy watching others play it — the place to add to your list of outdoor things to do in Chicago is the beautifully designed outdoor chess pavilion located just south of North Avenue Beach in the Lincoln Park neighborhood (just off the Lakefront Trail).  The structure has chessboards carved into it and they are sheltered from the elements by a wing-like overhang.  The structure, built in 1957, also features carvings of chess pieces as well as sculptures of free-standing pieces.

12. Chicago Riverwalk

Located on the south bank of the Chicago River between the lakefront and Lake Street, the Riverwalk is Chicago’s version of the Boardwalk in Atlantic City, it has something for everyone.  In addition to enjoying a leisurely stroll along a picturesque river, you can visit outdoor restaurants and taverns, museums, do a little fishing, take boat trips, try your hand at kayaking, view public art, and even do a little bird watching.

Outdoor things to do in Chicago - Visit the Chicago riverwalk

13. Beaches

For most of 2020, Chicago’s entire lakefront was “closed” — completely off-limits by order of Mayor Lightfoot as a way to prevent crowds from creating hotspots during the pandemic.  In 2021, the 26-mile lakefront is open again — free to anyone who wishes to swim, bike, stroll or picnic along the shore.  In addition to the parks and Lakefront Trail, Chicago’s more than two dozen beaches will also be open this summer (with proper social distancing).

14. Navy Pier

Normally open 365 days a year, Navy Pier was closed twice for extended periods of time during the pandemic — from March to June 2020 and from September 2020 to April 2021.  It is now in the process of a gradual reopening — all outdoor activities are operating but indoor facilities (such as retail shops, museums, theaters) are not open yet but expect to be when the summer months arrive.  Weekly fireworks displays have also returned to Navy Pier, 10-minute shows begin every Saturday night at 9 p.m.

Holder of two journalism degrees, including a masters from Northwestern University, Tom Schaffner is a native of the Chicago area and has spent nearly 50 years as a writer, editor, publisher and professional communications consultant. He was also the founder, editor, and publisher of the Chicago File, as well as the co-owner of L Stop Tours.

– By Tom Schaffner

If you enjoy reading about the history of Magic in Chicago and want to learn more about the city and its history, then consider signing up for our blog newsletter!

Magic, as a form of entertainment, has a long and checkered history in Chicago.

In 1893, two aspiring young magicians had a chance encounter on the Midway Plaisance at the Chicago World Columbian Exposition. Though both were employed as lowly sideshow performers at the fair, they agreed to share their magic secrets with each other in hopes of bolstering their acts. The two fledgling illusionists? Harry Houdini and Howard Thurston, both of whom would go on to become world-famous magicians in less than 20 years.  

Impressive Illusions

Because of their growing popularity, Houdini and Thurston would book themselves frequently into Chicago theaters where their shows were always sold-out. Houdini cemented his legend as an escape artist in 1898 when he escaped from a jail cell in Chicago’s South Loop Levee District after being bound by shackles and leg irons. The Great Thurston dazzled audiences with a trick in which playing cards mysteriously rose in the air and also with a floating lady illusion known as the “Levitation of Princess Karnac.” A third magician, Harry Blackstone, Sr. (a native Chicagoan who took his name from a famous local hotel) also began to make a name for himself around the turn of the century.  Blackstone’s most famous illusion was sawing a woman in half.

While big-time magic shows were popular in Chicago and in other cities across the country for a quarter of a century, they quickly fell out of fashion. Houdini’s death in 1926, the introduction of talking films in 1927, and the onset of the Great Depression effectively brought an end to big-time magic shows as a form of entertainment.  They were costly to stage, few audience members could afford the price of a ticket and there were cheaper options for entertainment, like motion pictures.

A New Kind of Magic Show

After World War II, however, the economy boomed and Chicagoans once again were on the lookout for new and different ways to amuse themselves.  In response, performers in Chicago pioneered a new type of “close-up” magic show, one that abandoned the large props and machinery of previous big-time magic acts in favor of smaller illusions (card tricks, disappearing objects, items emerging from a hat) that could easily be performed at a table or before an intimate crowd in a nightclub.

In the 1950s and ’60s, close-up magic flourished in Chicago.  Clubs like the Empire Room in the Palmer House and the Pump Room at the Ambassador East Hotel hired strolling magicians to entertain customers tableside. Schulien’s, in North Center, hired magicians to come to your table after your meal to perform a 10-minute show and the New York Lounge on Irving Park Road specialized in late-night magic shows (which ran until 4 a.m.).  Additionally, retail magic shops featuring all kinds of do-it-yourself magic tricks sprang up across the city, including five near Dearborn and Randolph in the Loop —Ireland’s, Joe Berg, Abbott’s, National Magic Company, and the Treasure Chest.

The Chicago Magic Scene Today

While magic as a form of entertainment — or retail enterprise — is not as popular in Chicago today as it was several decades ago, there still are a number of venues where you can enjoy up-close magic with your favorite food or beverage. There are also several independently-owned retail shops throughout the city that are devoted primarily to magician’s craft.  Because of the pandemic, some of these venues and stores have closed temporarily, limited their service hours or have created alternative programming.  Please check each listing’s website for accurate and timely information about business hours and operations. 

Ash’s Magic Shop (4955 N. Western)

Ashod “Mr. Ash” Baboorian was an immigrant from Iraq who loved magic.  He developed a comical magic act in the close-up Chicago style and began to play in area clubs and taverns in the 1960s and 70s.  In 1985, he decided to open his own magic shop in Lincoln Square, just down the street from the legendary New York Lounge.  The shop is crammed with tricks and other magic paraphernalia for beginners and professionals.  Though Mr. Ash recently passed away, his family is keeping the shop open, even during the pandemic.

Chicago Magic Lounge (5050 N. Clark St.)

Opened in 2015 in Andersonville as an homage to the close-up magic bars and restaurants of the past, this retro-styled venue (1930s-40s look and feel) features strolling magicians who do close-up card tricks and other illusions tableside for customers.  The Magic Lounge also has several small theaters in which to showcase tour magicians and related mystical entertainment.  Though the venue is “closed temporarily” during the pandemic, it does offer virtual cocktail hours every Friday evening and also has interactive virtual magic shows that can be arranged for private parties.

Midwest Magic (Franklin Park)

Staking out fertile magic territory in the suburbs is Midwest Magic, a retail store that carries more than 14,000 items and bills itself as “the largest magic shop in the world.”  In addition to tricks, gags, and related items, Midwest Magic claims to have one of the most comprehensive collections of books about magic in the industry.  The shop encourages patrons to “hang out” and interact with clerk/magicians who attempt to stump and amaze you by performing tricks from behind the counter.

The Magic Parlour (Palmer House Hotel)

Normally, magician Dennis Watkins performs an intimate, up-close magic show on weekends in a small showroom at the Palmer House Hotel.  However, the pandemic has temporarily halted the shows at the Palmer House, so Watkins has developed a virtual show, “The Magic Parlour at Home,” in which he delivers an interactive magic and mind-reading show directly to customers in their homes (via Zoom).

The Magic Penthouse (Kimpton Palomar Hotel)

Temporarily closed due to the pandemic, this is a monthly penthouse “party” (elegant cocktail attire, gourmet food, music, adult beverages) on the rooftop of a hotel that includes several wandering magicians who perform magic throughout the venue.  Pay one fee and you can enjoy a relaxing evening of food, booze and up-close magic.

Magic Inc. (1838 W. Lawrence)

This well-established retailer bills itself as “the world’s leading-edge magic source for magic tricks, magic books, magic DVDs, magic lessons and magic lectures.”  Catering to amateurs and professionals alike, the shop’s origins date to 1926 when it was located in the Loop and called Ireland Magic Company.  Several locations later, the store settled in Ravenswood where it still does a brisk business, boasting of an inventory of more than 10,000 items.

Holder of two journalism degrees, including a masters from Northwestern University, Tom Schaffner is a native of the Chicago area and has spent nearly 50 years as a writer, editor, publisher and professional communications consultant. He was also the founder, editor, and publisher of the Chicago File, a newsletter for former Chicagoans. Tom is also the co-owner of L Stop Tours.

If you enjoy reading about our picks for the best outdoor dining in Chicago, then visit our blog to get more insightful facts, recommendations and history about Chicago.

– By Lindsay McNaught


What’s not to love about summer in Chicago? Each year the warm weather brings renewed excitement for rooftop bars, restaurant patios, beer gardens, boat rides, Cubs games, street festivals, and strolls along the Riverwalk. Though the summer of 2020 has come with some limitations, there are still plenty of opportunities to soak in the sun and enjoy the outdoors in our beautiful city.  

In response to the pandemic, many Chicago restaurants have safely stepped up their outdoor dining game – more space, reduced capacity, socially-distanced tables, plenty of hand sanitizer  and clear guidelines regarding masks. Restaurants are also getting creative in other ways, such as offering contactless payment options and menus available on your phone via QR codes. Hopefully, we’ll see some of these new innovations outlast the pandemic. 

Check out our top picks for outdoor dining in Chicago:

  1. 5 Rabanitos
  2. Chef’s Special Cocktail Bar
  3. Frontier
  4. Green Street Smoked Meats
  5. Duck Inn
  6. Mott Street
  7. Big Star
  8. Parson’s Chicken & Fish

With more and more restaurants reopening and offering outdoor dining in Chicago, the city’s sidewalks are bursting with activity once again. But with so many delicious options, which do you choose? Here are eight of our team’s favorite restaurants that feature dining al fresco:

5 Rabanitos 

As far as outdoor dining in Chicago goes, 5 Rabanitos is hard to beat. Just steps from the 18th Street Pink Line Stop, this Pilsen eatery serves authentic Mexican cuisine at lunch and dinner. The restaurant’s patio on Wood Street sits just across the sidewalk from a beautiful mural painted on the building’s exterior. Join us next tour season for our Pilsen: Creativity and Community Tour to enjoy more of 5 Rabanitos before visiting the National Museum of Mexican Art. 

Chef’s Special Cocktail Bar

While they’ve been offering carryout food and to-go cocktails for a few months now, Chef’s Special recently launched a unique outdoor patio operation. After placing your order, your food is presented on a private windowsill next to your table so you and the servers are able to maintain a safe distance. You then move the food to your table and dig in. The menu features delicious Chinese cuisine and housemade cocktails from the team behind Giant. For those looking for outdoor dining in Chicago that involves eating delicious Chinese food and specialty cocktails, then Chef’s Special is your spot.


Serving up Southern comfort food, whole animals and large format meals, Frontier certainly offers a dining experience not found at other Chicago restaurants. When we arrived, the hostess greeted us with a hand sanitizer spritz before leading us to our outdoor table. Frontier is a Black-owned business and a James Beard Award Semi-Finalist. This same team also runs Ina Mae Tavern & Packed Goods, another Wicker Park restaurant serving New Orleans-inspired dishes with outdoor seating.

Green Street Smoked Meats

Green Street has successfully switched up its operations in order to accommodate the new outdoor dining in Chicago health codes. They’ve added more outdoor tables and spaced them farther apart. They’ve also switched from counter pick up to full service. Their smoked meats, sides and cocktail offerings are amazing — you can’t go wrong with anything on the menu.

Duck Inn 

Tucked between Pilsen and Bridgeport, this cozy tavern has a quaint patio and delicious food. Their specialties are rotisserie duck and Duck Inn dogs – their take on a classic Chicago hot dog. Both are excellent choices, depending on what you’re in the mood for. When we visited, we purchased extra dogs that came with instructions for preparing them at home. You can also find Duck Inn dogs at TimeOut Market, which reopened August 26 and is a stop on our Fulton Market: Winter on the West Side Tour.

Mott Street 

An Asian-fusion restaurant, Mott Street consistently offers unique and interesting dishes. To accommodate those who only want to do outdoor dining in Chicago, the patio has recently been extended. They allow small parties to be seated at large tables and everything feels safe and spread out. Mott Street also features family suppers to go and provides an opportunity for diners to purchase meals for frontline workers. This team also runs Mini Mott in Logan Square, an excellent spot for burgers, fries, and milkshakes.

Big Star

Big Star in Wicker Park remains a favorite among locals. They’ve expanded their already large patio and spaced tables to accommodate more diners safely. Their margaritas are refreshing on a hot day and dogs are welcome to hang out (on leashes, of course) while their owners enjoy delectable tacos and more. Our Wicker Park: Putting the Chic in Chicago Tour makes a stop at Big Star during tour season. 

Parson’s Chicken & Fish 

Both Parson’s locations have spacious patios with large picnic tables and delicious comfort food like fried chicken, hush puppies, and mac and cheese, to name a few. Unfortunately, real puppies aren’t allowed on the patio at this time but the good news is that Parson’s delivers and the food tastes just as good at home. We’ve ordered many hot chicken sandwiches over the course of the pandemic. Delicious.

Let’s continue to support our community and enjoy outdoor dining in Chicago while the weather cooperates.

– By Tom Schaffner

The Railway Capital of the US

Because of its strategic location in the center of the country — halfway between the Atlantic and Pacific Oceans and smack in the middle of America’s manufacturing and agricultural belts — Chicago has always been the undisputed railway capital of the United States.  Even today, more trains arrive in or depart from Chicago on a daily basis than anywhere else in the country (and likely the world).

Throughout history, Chicago and railroads have had a symbiotic relationship — both have helped each other grow into strong and viable entities.  Chicago contributed to the success of railroads by supporting their growth and development with flexibility and by providing a proactive regulatory environment; the railroads helped Chicago grow by moving billions of tons freight into and out of the city on a regular basis and by making the city a key hub in their network of passenger trains.

Additionally, Chicago made trains the centerpiece of its own public transportation system.  Beginning with the city’s first elevated railway in 1892 — the “Alley L” (the southern portion of today’s Green Line) — the city has made trains the primary conveyance for moving from neighborhood to neighborhood or one side of town to the other.


Top Train Museums

As the railway capital of the U.S., Chicago is fortunate to be located within a few hours’ drive of several of the nation’s best train museums:


  • Fox River Trolley Museum (South Elgin, IL) — The museum maintains a collection of 30 antique electric trolleys, railroad cars and locomotives and is focused on railways and transit lines of the Chicago area.  One of the museum’s prized pieces of equipment is the wooden interurban car #20 from the Chicago Aurora and Elgin Railroad. Constructed in 1902, car #20 is the oldest interurban car operating in the United States.


  • Illinois Railway Museum (Union, Il) — Located about 60 miles northwest of the city, the Illinois Railway Museum is the largest railway museum in the world.  Founded in 1953, the museum has in its collection 450 pieces of historic equipment, including steam engines, diesels, streetcars, interurbans and passenger and freight cars, many of which can be ridden on tracks that run throughout the site.  For fans of Chicago’s elevated transit system, a visit to Barn 8 is a must — it contains every type of L car that has run on the system since 1898.


  • Museum of Science and Industry (Chicago, IL) —  Though technically not a railway museum, the Museum of Science and Industry contains several historic locomotives, the opportunity to tour the Burlington Route’s 1934 Pioneer Zephyr, which was America’s first diesel-electric stainless steel Streamliner, and the world’s largest model train exhibit, “The Great Train Story,” which presents 2,200 miles of scenery and stories as a model train emulates the trip from Chicago to Seattle along 1,400 feet of track.


  • A. Philip Randolph Pullman Porter Museum (Chicago, IL) — There are no locomotives or passenger cars to examine or explore but that doesn’t make this museum any less important in the history of train travel in the U.S.  This museum, housed in Pullman National Historic Landmark District, contains a collection of artifacts and documents related to the Brotherhood of Sleeping Car Porters and celebrates the organization’s role in the U.S. labor movement.  The porters, most of which were African American, were employed by the manufacturer of the cars, George Pullman, and his Chicago-based Pullman Palace Car Company.


  • Mid-Continent Railway Museum (North Freedom, WI) — Located about a four-hour drive northwest of Chicago, the Mid-Continent Railway Museum has 13 steam locomotives and 7 diesel engines, including #1325 from the Chicago and North Western Railroad.  The museum also has the largest collection of wooden passenger cars in the United States, has six of only seven surviving wooden boxcars built by Mather Stock Car Company and has in its collection the nation’s last surviving fish car.


  • Hoosier Valley Railroad Museum (North Judson, IN) — Halfway between Chicago and Indianapolis is the Hoosier Valley Railroad Museum, which is located near the junction of four historic railroad lines — the Chesapeake and Ohio, the Pennsylvania, the New York Central and the Erie.  Founded in 1988, the museum has more than 30 pieces of rolling stock in its collection, including freight cars, cabooses, diesel switch engines and an Orton locomotive crane. The museum itself is housed in a station formerly owned by the Erie Railroad.


  • National New York Central Railroad Museum (Elkhart, IN) — The National New York Central Museum is dedicated to the preservation of the New York Central and includes several outdoor equipment displays, indoor model railroads, artifacts from the railroad and other exhibits pertaining to the history of railroading.  The museum consists of a modified New York Central Twentieth Century Limited train and a freight house built by the Lake Shore & Michigan Southern Railway in 1907.


  • New Buffalo Railroad Museum (New Buffalo, MI) — Located on the grounds of what was once the largest train yard in Southwest Michigan, the New Buffalo Railroad Museum is home to exhibits and collections recalling New Buffalo’s proud heritage as a railroad hub for both the Pere Marquette and Chesapeake & Ohio. The rail line behind the Museum still carries CSX freight trains through the stanchions of one of the original coal towers.  Visitors can stroll through a box car and ap Pullman Sleeper Car for military troops. 


  • Monticello Railway Museum (Monticello, IL) — About 18 miles west of Champaign, the Monticello Railway Museum is home to over 100 pieces of railroad equipment, including several restored diesel locomotives and cars.  Founded in 1966, the organization’s original goal was to encourage the Chicago Burling and Quincy Railroad to continue operating steam excursions for rail enthusiasts. When that effort failed, curators of the organization decided to operate their own steam excursions and, shortly, thereafter, a museum was born.

If you’re interested in visiting other museums in the city, many of our Chicago tours visit museums that cover all sorts of topics — from Chinese history to American economics. Learn more about L Stop Tours today!

Holder of two journalism degrees, including a masters from Northwestern University, Tom Schaffner is a native of the Chicago area and has spent nearly 50 years as a writer, editor, publisher and professional communications consultant. He was also the founder, editor, and publisher of the Chicago File, a newsletter for former Chicagoans. Tom is also the co-owner of L Stop Tours.

– By Tom Schaffner

The Warmest Place in Chicago

Where’s the warmest, sunniest place in Chicago during the winter months?  The Garfield Park Conservatory, of course.

Located about four miles directly west of the Loop — and only a few short steps from the CTA Green Line L Stop (Lake St. and Central Park Ave.) — the verdant, lush 4.5-acre Garfield Park Conservatory is a tropical resort that you can escape to whenever the winter weather in Chicago turns nasty.  With more than 2,100 plant species growing in 8 indoor spaces, the Garfield Park Conservatory is one of the largest greenhouse conservatories in the United States. Because of the variety of its plant collection as well as the unique design of the building, the Conservatory is often referred to as “landscape art under glass.”

A Little History

Constructed between 1906 and 1907, the Conservatory was conceived and designed by Chicago’s West Park Commission’s general superintendent and chief landscape architect, Jens Jensen. Hoping to create the “largest publicly owned conservatory under one roof in the world,” Jensen achieved his dream by consolidating smaller greenhouses in nearby Douglas and Humboldt parks into a new facility at Garfield Park.  Many of the plantings that survive today came from these smaller greenhouses. Jensen firmly believed that “the country must come to the city” and wanted the Conservatory to reflect the beauty that nature had to offer.

Current Conservatory

Today the Conservatory still follows the basic tenants of Jensen. The huge Palm Room contains over seven dozen varieties of palm trees, of which only 2,700 varieties are known to exist today; the Fern Room provides visitors with a glimpse of what Illinois looked like millions of years ago; the Desert Room holds one of the region’s most varied collections of cacti and succulents; and the Aroid Room contains many popular indoor houseplants.  The Conservatory also has a room that explains the process of photosynthesis, an indoor children’s garden, a show house that often hosts special shows and exhibits and 12 acres of beautiful outdoor gardens.

The Conservatory also hosts a number of special exhibits, concerts, classes and special events, including a Winter Flower show, a composting demo, yoga classes, botanical painting classes for seniors, a community holiday concert, beekeeping classes, and much more.

Holder of two journalism degrees, including a masters from Northwestern University, Tom Schaffner is a native of the Chicago area and has spent nearly 50 years as a writer, editor, publisher and professional communications consultant. He was also the founder, editor, and publisher of the Chicago File, a newsletter for former Chicagoans. Tom is also the co-owner of L Stop Tours.

– By Tom Schaffner

If you enjoy reading about the best parks in Chicago, then consider signing up for our blog newsletter!

With more than 600 parks comprising 8,800 acres of green space, the Chicago Park District is the largest municipal park manager in the nation.  It also is responsible for 28 indoor pools, 50 outdoor pools, and 26 miles of lakefront including 23 swimming beaches and one inland beach.

The city’s park system is also convenient.  A recent study found that 98 percent of all city residents live within a 10-minute walk — or roughly half a mile — of a public park.  In other words, serenity is not very far away.

Since we offer Chicago walking tours that utilize the L to visit neighborhoods throughout the city and suburbs, we’ve compiled a list of our favorite neighborhood parks that are also easily accessible via the L.

Best Parks in Chicago With Easy Access to the L

  1. Ping Tom Memorial Park (Via Green Line)
  2. Garfield Park (via Red Line) 
  3. Wicker Park (Via Blue Line)
  4. Douglas Park (Via Pink Line)
  5. Grant Park (Via Any Line Except Yellow)
  6. Gillson Park (Via Purple Line)
  7. Humboldt Park (Via Blue Line)
  8. Oz Park (Via Brown Line)

1. Ping Tom Memorial Park (Via Red Line)

Ping Tom Memorial Park

This beautiful 17.24-acre park is located on the south bank of the Chicago River, a few blocks from the Cermak-Chinatown stop on the CTA’s Red Line and, of course, the Chinatown neighborhood (which you see more of on our Chicago Chinatown Food Tour.). Named for Ping Tom, a prominent Chinatown businessman and civic leader, the park was created in October 1999 and features a pagoda-style pavilion, bamboo gardens and a playground.  In warmer weather, the Chicago Water Taxi makes scheduled stops at Ping Tom Park from various downtown locations.


2. Garfield Park (Via Green Line)

Garfield Park Chicago

Only steps from the Green Line, Garfield Park is a 184-acre green space that was designed by William LeBaron Jenney, architect of the world’s first skyscraper (Chicago’s Home Insurance Building). It is the oldest of the city’s three original West Side Parks, which include Humboldt Park and Douglas Park. The centerpiece of the park is the 4.5-acre Garfield Park Conservatory, one of the largest greenhouse conservatories in the United States.  Open year-round, the conservatory is particularly enticing in the middle of winter when it offers visitors an escape from the white snow into a world of green. You can experience the Garfield Park Conservatory during our Fulton Market tour!


3. Wicker Park (Via Blue Line)

Wicker Park Chicago

Though only four acres, Wicker Park is a much-beloved and widely-used community park in the heart of one of Chicago’s toniest neighborhoods. Located only steps from the Blue Line L stop at Damen, Wicker Park is dog-friendly and includes baseball diamonds, a walking path, a spray pool and a water playground for children and a statue of Charles Wicker, who, with his brother Joel, donated the park to the community in hopes that it would one day spur development within the community.  It did, perhaps well beyond even the wildest dreams of the Wicker brothers.


4. Douglas Park (Via Pink Line)

Douglas Park Chicago

A short walk from the Pink Line station at California is Douglas Park, named in honor of Stephen A. Douglas, a U.S. Senator from Illinois who lost the 1860 presidential race to Abraham Lincoln, also from Illinois. Spanning 173 acres and straddling a few neighborhoods on the city’s West Side (Pilsen and North Lawndale), Douglas Park was built for recreation. It currently houses a miniature golf course, five playgrounds, an outdoor swimming pool, soccer fields, basketball courts and an oval running track.  It also features a beautiful lagoon, a wide variety of trees, and an old stone bridge. You can see more of what the Pink Line offers on our Pilsen Chicago Neighborhood tour!


5. Grant Park (Via Any Line Except Yellow)

Grant Park Chicago

Also proudly referred to as “Chicago’s Front Yard,” Grant Park is one of the city’s largest green spaces, stretching from Randolph St. on the north to the Museum Campus on the south, Michigan Ave. on the west and Lake Michigan on the east.  In addition to baseball diamonds, soccer fields, tennis courts and breathtaking gardens, Grant Park also hosts innumerable food and music festivals and other special events throughout the year. Also part of the greater Grant Park area are Millennium Park, Maggie Daley Park, Buckingham Fountain, The Art Institute, The Field Museum, Shedd Aquarium, Adler Planetarium and two leisure boat harbors.  The 313-acre park, one of the largest in the city, can be accessed by any L (except the Yellow Line) at stations throughout the Loop.


6. Gillson Park (Via Purple Line)

Gillson Park Chicago

Located in the nearby suburb of Wilmette, Gillson Park is a half-mile walk from the Linden Avenue stop on the CTA’s Purple Line. This beautiful 60-acre park is located on the shore of Lake Michigan and features a public beach, picnic facilities, sailboat and kayak rentals, bicycling, soccer tennis and a wide variety of other recreational activities.  Named for the first president of the Wilmette Park District’s Board of Commissioners, Louis K. Gillson, the park opened to the public in 1910.


7. Humboldt Park (Via Blue Line)

Humbholdt Park Chicago

Humboldt Park is a 207-acre park on the West Side of Chicago that is located in a community of the same name.  The park was named for Alexander von Humboldt, a well-known geographer and naturalist in the mid-1800s. The park features three major historical public buildings, including the Boat House (now a café overlooking the lagoon); the Field House, which includes a fitness center, two gymnasiums, meeting rooms and an inland beach; and the historic Humboldt Park Stables, which is in the process of being converted to the National Museum of Puerto Rican Arts and Culture.  Humboldt Park is a 20-minute walk from the Blue Line Damen Ave. stop.


8. Oz Park (Via Brown Line)

Oz Park Chicago

Located in the Lincoln Park neighborhood, Oz Park takes its name from a novel written by Lyman Frank Baum, a former resident of the neighborhood who wrote “The Wonderful Wizard of Oz.”  The 13-acre park features sculptures of characters from the novel, The Tin Man, the Cowardly Lion, the Scarecrow and Dorothy and Toto. “The Emerald Garden,” located at the northeast corner of the park, has a path of flowers that visitors can walk through; nearby is “Dorothy’s Play Lot,” which includes swings and climbing equipment for children.  Oz Park is located a few blocks from the Brown Line Armitage stop. You can see more of what the Brown Line has to offer on our Historic Pub Tour.

Holder of two journalism degrees, including a masters from Northwestern University, Tom Schaffner is a native of the Chicago area and has spent nearly 50 years as a writer, editor, publisher and professional communications consultant. He was also the founder, editor, and publisher of the Chicago File, a newsletter for former Chicagoans. Tom is also the co-owner of L Stop Tours.

– By Tom Schaffner

Learn more about the Bloomingdale Trail (the 606) and its history in Chicago.

The Bloomingdale Trail

We generally use this space to write about Chicago’s elevated transit system, the “L.”  Our business, L Stop Tours, is all about the L and the 77 city neighborhoods it passes through.  Today we’re going in a slightly different direction and writing about a different elevated railroad system, the Bloomingdale Trail and its larger park-encompassing cousin, the 606.

The Bloomingdale Trail is a former elevated railway line that the City of Chicago converted into an elevated greenway in 2015.  It runs west from Ashland Avenue (along W. Bloomingdale Avenue) to Ridgeway Avenue (3732 west). At 2.7 miles in length, the Bloomingdale Trail is the second longest greenway project of a former elevated rail line in the world, trailing only the Promenade Plantée in Paris (2.9 miles in length).  Today the only traffic on the Bloomingdale Trail are hikers, bikers, joggers and pedestrians of all shapes and sizes.

Bloomingdale Trail Construction

Originally constructed in 1873 by the Chicago and Pacific Railroad Company as part of a 36-mile link to Elgin, Illinois, the railroad was built at street level and carried both passenger and freight traffic.  In the 1910s the railroad was elevated approximately 20 feet when as ordinance designed to reduce pedestrian fatalities at street level was passed by the City of Chicago. As businesses began to move out of the area (such as Schwinn Bicycle Company), freight traffic on the rail line began a long, steady decline into irrelevancy.  The last freight train ran on the line in 2001.

Though the City of Chicago had investigated converting the Bloomingdale Line into a greenway as early as 1997, it wasn’t until 2004 that the project was revisited and made part of the Logan Square Open Space Plan, which prosed a linear park with public access ramps every few blocks.  Groundbreaking for the project occurred on August 27, 2013. In addition to extensive landscaping and access ramps, the trail consists of a 10-foot wide paved path with a 2-foot soft shoulder on either side.

The Bloomingdale Trail is central to a larger series of parks and a trail network in the area called “The 606,” which derives its name from the first three digits of all Chicago ZIP Codes.  The intent is to symbolize the linkage between parks and the neighborhoods they serve, as opposed to the elevated rail line which served to isolate and “wall off” neighborhoods. The four newly-linked neighborhoods are Wicker Park, Bucktown, Humboldt Park and Logan Square.

Access to the Bloomindale Trail via public transportation from downtown is easy — take the CTA Blue Line to either Damen or Western Avenues.

Bloomingdale Trail

Holder of two journalism degrees, including a masters from Northwestern University, Tom Schaffner is a native of the Chicago area and has spent nearly 50 years as a writer, editor, publisher and professional communications consultant. He was also the founder, editor, and publisher of the Chicago File, a newsletter for former Chicagoans. Tom is also the co-owner of L Stop Tours.

– By Tom Schaffner

While it’s important to keep up with the latest trendy restaurants in town, it’s also important to keep tabs on those eating places known as  “joints” — places that have been around forever, have one or several signature items on their menu, have been popular for years, are small, independent or family-owned (not a franchise or corporate chain) and, as often is the case, are unabashedly dowdy in their design, décor and appearance. What you’re about to discover is simply the best food in Chicago.

In my family, we keep tabs on various joints around the city by making it a point to visit one — either a long-time favorite or a new one we’ve just discovered — about once a month. We generally go on Saturdays, usually for lunch,  because the time slot allows plenty of time to sleep on a Saturday morning and also because, well, there’s no rush to get back to the office or workplace. On Saturdays, there’s plenty of time to fully wallow in the “joint” experience and savor the food you have purchased.

So with no further ado, here is a list of our very favorite Chicago food joints that we have compiled over the years for your dining pleasure:

Best Food Joints in Chicago

Stony Sub (8440 S. Stony Island Ave.)

You can’t miss the bright yellow building on the west side of Stony Island just past 84th. Inside the structure, every square inch of wall space is covered with signs offering everything from burgers to gyros, wings to subs. Stony Sub is a cash-only joint that offers only food to go. We visited Stony Sub in the summer and took our food across the street and enjoyed a picnic of sorts on the grassy, park-like median that separates Stony Island’s north- and southbound lanes.

Signature Dish:  The uniquely Chicago Gym Shoe Sandwich (also known in various parts as the Jim Shoe), which consists of gyro meat, roast beef and corned beef stacked high on an Italian roll with lettuce, tomato, tzatziki sauce (Greek yogurt), Swiss cheese, onions, sweet peppers and giardiniera (hot pickled Italian relish). It doesn’t get any more Chicago than this!

Jim Shoe Sandwich – LTHForum

Ricobene’s (252 W. 26th)

Open since 1946, this South Side Italian eatery is located in Bridgeport but is difficult to find. It’s boxed in by two overhead expressways (I-55 on the north and I-90/94 on the south) and also by an above ground rail switching yard immediately west of the restaurant. During the lunch hour you’ll find all types of customers dining there — truck drivers, executives, factory workers and, yes, railroad employees.

Signature Dish: Ricobene’s is known far and wide for its breaded steak sandwich, a massive pile of beef smothered in cheese, peppers, giardiniera and marinara, all of which are packed tightly inside a split French roll. In 2015, USA Today named Ricobene’s breaded steak sandwich the “Best Sandwich in the World;” Anthony Bourdain liked it so much he featured it on his “Parts Unknown” travel show. Years ago, a friend of mine ordered one and just stared at the massive Frisbee-sized concoction when it was placed in front of him. He then looked up, shook his head and said, “This thing’s as big as a disk brake.” It was. But over the next hour or so, he ate every morsel.


Half Shell (676 W. Diversey Pkwy.) 

It’s like a little, divey neighborhood bar with kitchy nautical decorations that’s located in the basement of someone’s house, but with one notable exception — this little subterranean gem serves great seafood at great prices. 

Signature Dish:  Alaskan King Crab legs with herbed garlic butter are extremely popular at the Half Shell, they’re cooked well and you get a lot of them. One reviewer suggests you bring your own kitchen shears so you can attack the pile of shellfish faster. Great advice.


Taurus Flavors (8534 S. Stony Island Ave.)

The name refers to the original business, an ice cream shop, which was opened at this location in 1966. Some of the unique ice cream flavors are still on the menu, such as black walnut, butter pecan and praline. This is a “joint” in the truest sense of the word, great food (mainly sandwiches) is offered to go (cash only) and the service is fast and the building itself resembles a trailer or mobile home with the windows propped up.

Signature Dish:  The Steak Sweet sandwich, a combination of chopped rib-eye steak, seasonings, grilled onions, cheese, sweet peppers and tomatoes that comes on a steamed bun and is topped with a sweet-savory sauce.


Calumet Fisheries (3259 E. 95th)

You would never suspect that this little, weathered wooden building with the hand-painted signs just a few feet from the Calumet River actually is a James Beard Foundation Award-winning restaurant. It opened in 1948 and is owned and operated today by the same founding family. Without question, it’s some of the best food in Chicago.

Signature Dish:  Calumet Fisheries is essentially a smokehouse, you cannot go wrong with anything on the menu that is smoked, particularly the smoked sturgeon, trout and shrimp.


Lindy’s Chili (3685 S. Archer Ave.)

Like most “joints,” there’s nothing fancy here, just a small bar, several tables and walls that are covered with signs and old photos.  Lindy’s claims to be “Chicago’s Oldest Chili Parlor” and it probably is — it was founded on this spot in 1924.

Signature Dish:  You can order the chili with beans, with mac, without beans, without mac or ladled on top of just about anything, like hot dogs, nachos or burgers.


Cemitas Puebla (817 W. Fulton St.) 

Located in Humboldt Park since 2002, this Mexican eatery recently relocated to Fulton Market where it now sports a new, trendier look. Cemitas refers to a sandwich resembling a torta that originates from the Puebla region of Mexico.

Signature Dish: Cemitas Atomica, a breaded pork chop, a chile guajillo marinated pork chop, and ham, along with Oaxacan cheese and avocado served on sesame seed bread.


Johnny O’s (3465 S. Morgan)

Another classic Bridgeport “joint,” Johnny O’s, is a 55-year-old establishment that is kind of a business mash-up — it’s part hot dog stand, part diner, part convenience store and part restaurant. Its split personality aside, they serve fast food that tastes great and is widely considered to be some of the best food in Chicago.

Signature Dish:  The Mother-in-Law, a tamale in a hot dog bun, covered with chili and then topped with relish, onions, peppers and tomato slices. 


Friistyle (5059 S. Prairie)

Open only for about a year, this South Side eatery has already achieved “joint” status. It serves only dishes that are versions of Belgian-style pommes frites, or, French-fries that are covered with decadent sauces and your choice of protein, such as roast lamb, jerk salmon or chicken wings. 

Signature Dish:  Italian Beef Frite, Chicago-style Italian beef, Asiago, giardiniera cheese sauce and au jus on a bed of fresh pomme frites.


Johnnie’s Beef  (7500 W. North Avenue, Elmwood Park)

A no-nonsense, one-story building with a big glass window that reveals a long line of customers who are waiting for their piping hot Italian beef sandwiches. It has looked this way since the joint opened in 1961.

Signature Dish:  Italian Beef, thin slices of seasoned roast beef, simmered and served au jus on a long Italian style roll, usually with giardiniera and sport peppers.


Looking to try some of the best food in Chicago for yourself? Great! Check out our list of Chicago tours now and you could be elbows deep in giardiniera before you know it!

Holder of two journalism degrees, including a masters from Northwestern University, Tom Schaffner is a native of the Chicago area and has spent nearly 50 years as a writer, editor, publisher and professional communications consultant. He was also the founder, editor, and publisher of the Chicago File, a newsletter for former Chicagoans. Tom is also the co-owner of L Stop Tours.

Take a Chicago tour through Instagram and you’ll find diverse and dynamic neighborhoods with many incredible places that would be ideal for the perfect Insta shot. If you’re looking for some of the most Instagrammable places in Chicago, consider these Instagram favorites below and discover some other hidden gems to fill up the social feed that you won’t find anywhere else.

Instagrammable Places in Chicago

  1. The River Walk
  2. The Lions at the Art Institute of Chicago
  3. The Flamingo Rum Club
  4. Calder’s Flamingo
  5. Cloudgate (The Bean) at Millenium Park
  6. Cindy’s Rooftop
  7. Skyline from North Ave. Beach
  8. 3 Arts Cafe at Restoration Hardware
  9. The Stairs in the Rookery Building
  10. Garfield Park Conservatory


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1. Anywhere on the River Walk

By far one of the most popular Instagrammable places in Chicago is the newly refurbished Chicago River Walk. Whether you’re on one of the many bridges or right along the waterfront, there are perfect views from every angle.


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2. The Lions at the Art Institute of Chicago

Located at 111 S. Michigan, the Art Institute is the epicenter of culture in Chicago. It’s also home to two famous Chicagoans: the lions which front the museum. They are well known the world over, and instantly recognizable to your Instagram followers.


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3. The Flamingo Rum Club

After powering through a mojito or a few mai tais, step outside this popular Wells St. establishment to pose for a few Insta shots in front of the famous flamingo mural. You may have to wait in line (for the mural) but it’s worth it.



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4. Calder’s Flamingo

What is it with this city and flamingos? One of the most iconic sculptures in Chicago, the twisted, 53-foot tall, rust-colored flamingo is definitely one of the most impressive sites in the city. And it’s conveniently located off the Brown Line at State and Van Buren at the Harold Washington Library (not a bad place for a few photos either). It could be argued that Calder’s Flamingo is easily one of the best downtown attractions and most Instagrammable places in Chicago.


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5. Cloudgate (The Bean) at Millenium Park

No Instagram trip to Chicago would be complete without spending some time in Millenium Park at the Bean (also known as CloudGate). Perfect from every angle, and super fun underneath, go early and stay late and then jump on the Red or Brown Line in moments to tour Chicago like the locals!


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6. Cindy’s Rooftop

One of the most stunning vistas in all of Chicago, Cindy’s Rooftop in the Chicago Athletic Club provides a perfect view of downtown, Millenium Park and the lakeshore that will fit perfectly in your Instagram feed.


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7. Skyline from North Ave. Beach

Venturing just a few train stops away from downtown on the Brown Line or Red Line (at the Eastern end of North Avenue, is one of the most impressive gateways to the lakefront. Just look south at any time of day (preferably at night) and you’ll be greeted by one of the most stunning views of all Chicago.


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8. 3 Arts Cafe at Restoration Hardware

You can only really be outside for three or four months of the year. So where do the hippest and most influential Instagrammers of Chicago go when they need the perfect shot? That’s right – 3 Arts Cafe. A glorious patio outside and high ceilings on the interior with lots of natural light, it’s the perfect location for a memorable Instagram shot.


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9. The Stairs in the Rookery Building

Chicago is known for its skyscrapers but there’s a lot more to architecture than just the outside of a building. The landmark Rookery Building on LaSalle Street features a mesmerizing oriel staircase and an amazing light court which is sure to make your Instagram followers applaud your trip to Chicago.


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10. Garfield Park Conservatory

A long winter in Chicago doesn’t mean that nature isn’t around – this is the “City in A Garden” after all, but sometimes that garden is indoors! Just a short ride from downtown (this destination is also part of L Stop’s Chicago Pedway tour), the warm and semi-exotic air of one of the nation’s top indoor gardens presents two whole acres of photo-worthy nature moments in some much needed warm air.

There are, of course, far more Instagrammable places in Chicago that we didn’t mention! If you’re looking for a Chicago city tour guide that knows all the right Instagram spots, check the schedule for upcoming Chicago walking tours and find some real hidden gems.

– By Tom Schaffner

When I was in my early twenties, I worked in an office on North Michigan Avenue near the Wrigley Building.  My home at the time was in East Lakeview — 3.7 miles north of the office.

Tom's Ultimate Chicago Pub CrawlEvery day after work I had a difficult transportation decision to make in order to get home — take the L (usually too crowded), take the bus (generally too slow) or take a cab (always too expensive).  There were no ride-sharing businesses in those days and even if there had been, we didn’t have smartphones with which to initiate an order. Many evenings I chose to walk home, a journey that would take about one hour and 15 minutes if no stops were made along the way.

When I wasn’t in a hurry, I’d take my sweet time and make all kinds of stops on the way home. The best walks were those where I explored the many bars, taverns, and saloons that populated my meandering path home.  After much trial and error, I developed a sacred list of favorite establishments — a list that I would later describe as “The Ultimate Pub Crawl.”  It was a wide array of drinking establishments — old standards, singles bars, places with happy hour and appetizer specials, bars with 4 a.m. licenses, and many more.  Literally, a cornucopia of drinking joints.

Although many of my favorites vanished long ago, the vast majority of “Ultimate Pub Crawl” joints are, incredibly, still in business 40 years later — a testament to their stamina and staying power. Here, in proper order, is the “Ultimate Pub Crawl” — drinking establishments that were popular in 1980 and are still going strong:

Chicago Pub Crawl

  • Billy Goat Tavern
  • Pippin’s Tavern
  • Hangge-Uppe
  • Butch McGuire’s
  • The Lodge
  • Old Town Ale House
  • Marge’s Still
  • Kincade’s Bar & Grill
  • Glascott’s Groggery
  • Burwood Trap
  • Durkin’s

Billy Goat Tavern (430 N. Michigan Ave.) 

A dingy, subterranean watering hole that screams “old school” from the second you descend the steps from the front door.  The place hasn’t changed a bit in 40 years — a thin film of brown grease (from years of frying “dobla-cheez” burgers) taints the pictures and other framed objects on the walls and laminate tabletops feature red and white checkered squares that are printed on them.  From the “Billy Goat Curse” to the famous sketch depicted on Saturday Night Live, Billy Goat Tavern is a bar that should be on every Chicago pub crawl.

Pippin’s Tavern (39 E. Chicago Ave – Recently moved)

A ten-minute walk from Billy Goat, Pippin’s is a great little tavern that has been serving thirsty Chicagoan’s since the 1970s.  Unlike other establishments in the area, Pippin’s is small and unpretentious with a cozy, comfortable feeling to it. Back in the day, Pippin’s was frequented by airline crew members who were overnighting at nearby Michigan Avenue hotels; today it attracts a wide array of guests, serves upscale food, and is open only until midnight (however, its nearby sister tavern, Streeter’s, retains a 4 a.m. liquor license).

Hangge-Uppe (14 W. Elm)

I would have voted this bar the “Least Likely to Survive as a Business” in 1980 but here we are, more than 40 years later, and the Hangge-Uppe is still going strong.  Upstairs is still “disco-like” with a lit dance floor and DJ; downstairs is the self-proclaimed “Rock and Roll Heaven” which features a number of bars, loud, piped-in rock and roll music and wall-to-wall-people.  The Hangge-Uppe is a great place to have a drink, people watch, and then move on to the next bar.

Butch McGuire’s (20 W. Division)

Butch McGuire opened this tavern on Division St. in 1961 and in so doing, created the world’s first “Singles Bar,” a place where it would be easy for people to meet one another, enjoy quality food and cocktails and have a good time.  Over the years the bar claims to have served more than 23 million glasses of beer and is single-handedly responsible for thousands of people not only hooking up but, ultimately, getting married. Though the nightclub intensity of Division and Rush Street has dropped considerably in recent years, Butch McGuire’s is still a good place to get a drink on your long walk to Lakeview.

The Lodge (21 W. Division)

Located across the street from Butch McGuire’s, the Lodge Tavern pre-dates Butch’s by four years, making it the senior member of the Rush Street entertainment district.  By Rush Street standards, the Lodge is on the small side and feels quite crowded on a Friday or Saturday night when things get cranked up. For the Ultimate Chicago Pub Crawl, it’s worth a shot and beer…and then on your way.

Old Town Ale House (219 W. North Ave)

Perhaps the “diviest” bar on the Ultimate Chicago Pub Crawl, the Old Town Ale House knows what it is…and is proud of it.  Cheap beers, sawdust on the floor, old books scattered throughout and veteran tipplers seated at the bar who’ve been coming here for years.  The original bar caught fire and then moved across the street to the current location in 1971. It was supposed to be a temporary move but the bar is still there today.  You won’t find a drinking joint in Chicago with more “character” than this one.

Marge’s Still (1758 N. Sedgwick)

Every Chicago pub crawl has to have the quintessential corner tavern on its agenda and for the Ultimate Pub Crawl, Marge’s Still fits the bill.  The building it is housed in dates to 1885 and the tavern was operated as a speakeasy during Prohibition (gin was made in the bathtub on the second floor). Previous owner Marge Lednick passed on in 2001 but the bar survives with her name.

Kincade’s Bar & Grill (950 W. Armitage)

Established in 1986, Kincade’s is one of the “younger” bars on this circuit.  It is primarily a sports bar and has special allegiances with certain college teams, such as Northwestern University and the University of Kansas, which is odd because DePaul University is literally right across the street.  The bar is convenient to the Brown Line (elevated train) in case you are looking to abandon the pub crawl early.

Glascott’s Groggery (2158 N. Halsted)

You are now officially in Lincoln Park and if you are still hoofing it from bar to bar, you have walked 2.9 miles from Billy Goat Tavern.  Congratulations, you deserve a drink. Glasscott’s, run by various members of the Glascott family since 1937, offers 15 beers on tap, more in bottles, wine by the glass and a wide variety of liquor.  The décor inside is classic Chicago neighborhood bar — mahogany bar, tin ceiling, white hexagonal floor tile, high backed wooden barstools and a game room in the back.

Burwood Tap (724 W. Wrightwood) 

Another tavern owned and operated by the same family since 1933.  Inside the bar is a large photograph of Burwood regulars — one of them is named Leroy Brown and he served in the Navy with a songwriter by the of Jim Croce, who would later write a song about him called, “Bad, Bad Leroy Brown.”  Located in the middle of a quiet residential neighborhood, Burwood Tap is a classic neighborhood bar.

Durkin’s (810 W. Diversey Pkwy)

The last stop on the Chicago pub crawl is Durkin’s which, since 1933, has held the longest continuous beer license on the city’s North Side.  It calls itself an Irish bar, but it’s really just another neighborhood sports bar — lots of large-screen televisions with sports on all the time. This is a shot and a beer joint — drink up, pub crawlers.

Tom on a Chicago Pub Crawl

There you have it — 11 bars, 3.7 miles, all on foot.  The Chicago pub crawl requires pacing and a bit of stamina, no doubt about it.  But it is a beautiful walk, on the way you see North Michigan Avenue, the Rush Street entertainment district, Old Town, DePaul, Lincoln Park and Lakeview.

Happy pubbing (or crawling, as the case may be).


Holder of two journalism degrees, including a masters from Northwestern University, Tom Schaffner is a native of the Chicago area and has spent nearly 50 years as a writer, editor, publisher and professional communications consultant. He was also the founder, editor, and publisher of the Chicago File, a newsletter for former Chicagoans. Tom is also the co-owner of L Stop Tours.