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What To Do in The Loop

May 29, 2019

– By Tom Schaffner

What To Do in The Loop

The Loop is one of Chicago’s 77 community areas. It is named for the elevated trains that form a loop over the streets. The area extends beyond the actual train loop, however. Within the area are several neighborhoods and districts including Printers Row, Jewelers Row, and the Theatre District. In addition, the area was also once home to the world’s first skyscraper, the Home Insurance Building. 

In recent years, new growth and development have started attracting more tourists and locals. Beyond the usual tourist attractions, The Loop has a lot to offer. 


Things to Do

Stroll Lakefront Trail — Walk, skate, scoot or pedal Chicago’s 18.5 mile trail along the Lake Michigan shoreline.

Hang out on the Riverwalk — Enjoy shops, restaurants, taverns and more on this 1.25-mile walkway along the south bank of the Chicago River.

Ride the Water Taxi — the Water Taxi picks up along the Chicago River and takes visitors to several neighborhoods including Chinatown. Find the schedule here.

Check out Millennium Park — Music, sculpture, gardens, fountains and more await you at this urban oasis located at Randolph St. and Michigan Ave.

Visit the Art Institute —Visit what is regularly rated as one of the top art museums in the world.

See Buckingham Fountain —Beautiful by day, even more beautiful at night with a spectacular 20 minute light and music display every hour on the hour.

Peek into the Harold Washington Library — In addition to the usual library resources, this “new” library (built 1991) contains a wide variety of interesting exhibits, archives and a beautiful Winter Garden on the ninth floor. 

Check out The Cultural Center – This building houses the largest Tiffany Dome in the world along with many other exhibits.

Visit the Gene Siskel Film Center — A center for film enthusiasts with more than 1,500 screenings and 100 guest artist appearances annually.

Visit the American Writers Museum — A unique museum of American literature and writers that opened in 2017.



London House – Enjoy a cocktail and a spectacular view of Chicago from the rooftop terrace on the 22nd floor of the London House Hotel.

Cindy’s – Dine, sip beverages and enjoy the view from the outside balcony at Cindy’s, located on the top floor of the Chicago Athletic Association Hotel.

The Game Room – Also located in the CAA Hotel, this bar offers many games such as shuffleboard, chess and foosball along with drinks and snacks.

Buddy Guy’s Legends – Eat, drink and enjoy the blues at the club of one of Chicago’s true originals, Buddy Guy.

Miller’s Pub –Serving American cuisine, pub food and cocktails to Chicagoans since 1935.

Morton’s The Steakhouse – Steakhouse restaurant (now a chain of restaurants) founded by legendary Chicago restaurateur Arnold Morton.

Prime and Provisions – A vibrant and modern steakhouse drawing inspiration from 1920’s supper clubs.

The Berghoff – A Chicago tradition serving authentic German food and drink to patrons since 1898.

Trattoria #10 — Classic Italian food in an intimate, elegant setting; it is popular with the theatre-going crowd.

Catch 35 — High-end Chicago restaurant focuses on seafood but also has steaks, salads and bar food on the menu.

Monk’s Pub – A decades-old pub with craft beer and pub fare.

AceBounce – A Ping Pong Bar and Restaurant were guests can rent tables in 30-60 minutes increments and enjoy cocktails.


Now that you know what to do in the loop, make your reservation with L Stop Tours and see Chicago like Chicagoans! 

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.

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Elevated Train Tracks above the streets and between buildings at The Loop in Chicago

Duration: 3.5 hours

Price: Adult $60

  • Tour price includes transit fees. Food/beverages purchased by guests.
  • Tour begins and ends in the Loop.
  • Walking distance: 1.5 miles
group of people sitting around table with drinks on the Chicago pub tour

Duration: 3.5 hours

Price: Adult $60

  • Price includes transit fees. Food/beverages purchased by guests.
  • Tour begins and ends in the Loop.
  • Walking distance: 1.1 miles
Tourists in Chicago on a tour looking up at Skyscrapers

Duration: 2.5 hours

Price: Adult $60

  • Tour price includes professional tour guide, train ride. Food/beverages purchased by guests.
  • Tour begins and ends in the Loop.
  • Walking distance: 1.5 miles


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