What To Do in The Loop

– By Tom Schaffner

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. 

 

Top Things to Do in the Loop

1. Stroll the Lakefront Trail
   Walk, skate, scoot, or bike Chicago’s scenic 18.5-mile trail along the Lake Michigan shoreline. It’s one of the best places to enjoy the beauty of the city and its lakeside views.
2. Hang Out on the Riverwalk
   The Chicago Riverwalk is a 1.25-mile path along the river, offering shops, restaurants, bars, and stunning views of the city. It’s a perfect spot to relax, people-watch, or enjoy a drink.
   Chicago Riverwalk
3. Ride the Water Taxi
   Hop on the Water Taxi for a unique way to explore the city. It stops at several neighborhoods, including Chinatown, giving you a new perspective of Chicago from the water.
   Chicago Water Taxi
4. Explore Millennium Park 
   This urban oasis at Randolph St. and Michigan Ave. is home to famous sculptures, beautiful gardens, fountains, and free concerts. Don’t miss the iconic Cloud Gate sculpture (aka “The Bean”).
   Address: 201 E Randolph St, Chicago, IL 60602
5. Visit the Art Institute of Chicago
   Regularly ranked as one of the top art museums in the world, the Art Institute is a must-see for culture lovers. It’s home to thousands of artworks, including masterpieces by Monet, Van Gogh, and Grant Wood.
   Art Institute of Chicago
   Address: 111 S Michigan Ave, Chicago, IL 60603
6. See Buckingham Fountain
   Known for its impressive beauty, Buckingham Fountain is a Chicago landmark. Enjoy it by day, but make sure to catch the spectacular 20-minute light and music show every hour at night.
   Address: 301 S Columbus Dr, Chicago, IL 60605
7. Peek into the Harold Washington Library
   This modern library (built in 1991) offers more than just books. It features intriguing exhibits, archives, and the beautiful Winter Garden on the ninth floor, a peaceful spot to relax.
   Address: 400 S State St, Chicago, IL 60605
8. Discover the Cultural Center
   Home to the largest Tiffany Dome in the world, the Cultural Center also hosts art exhibits, performances, and cultural events throughout the year.
   Address: 78 E Washington St, Chicago, IL 60602
9. Visit the Gene Siskel Film Center
   A paradise for film lovers, the Gene Siskel Film Center hosts over 1,500 screenings a year, with a diverse lineup of films and guest artist appearances.
   Gene Siskel Film Center
   Address: 164 N State St, Chicago, IL 60601
10. Explore the American Writers Museum
    Opened in 2017, this unique museum celebrates American literature and its most influential writers, offering interactive exhibits and engaging storytelling.
    American Writers Museum
    Address: 180 N Michigan Ave, Chicago, IL 60601

Best Bars and Restaurants in the Loop

1. London House
   For spectacular views of the Chicago skyline, head to the rooftop terrace at the London House Hotel. Enjoy a cocktail while taking in the breathtaking sights of the city.
   London House
   Address: 85 E Wacker Dr, Chicago, IL 60601
2. Cindy’s
   Located at the top of the Chicago Athletic Association Hotel, Cindy’s offers outdoor seating with stunning views, along with delicious food and drinks.
   Cindy’s
   Address: 12 S Michigan Ave, Chicago, IL 60603
3. The Game Room
   If you’re in the mood for some fun, The Game Room at the CAA Hotel offers games like shuffleboard, chess, and foosball along with great drinks and snacks.
   The Game Room
   Address: 12 S Michigan Ave, Chicago, IL 60603
4. Buddy Guy’s Legends
   Enjoy live blues music and classic Chicago pub food at this legendary venue, named after the iconic blues guitarist Buddy Guy.
   Buddy Guy’s Legends
   Address: 700 S Wabash Ave, Chicago, IL 60605
5. Miller’s Pub
   Serving Chicagoans since 1935, Miller’s Pub offers hearty American cuisine, pub favorites, and cocktails in a cozy, historic setting.
   Miller’s Pub
   Address: 134 S Wabash Ave, Chicago, IL 60603
6. Morton’s The Steakhouse
   A classic Chicago steakhouse, Morton’s is known for its high-quality steaks, seafood, and elegant dining atmosphere.
   Morton’s The Steakhouse
   Address: 65 E Wacker Pl, Chicago, IL 60601
7. Prime and Provisions
   For a modern twist on the classic steakhouse, Prime and Provisions offers a vibrant atmosphere and delicious cuts of steak, inspired by 1920s supper clubs.
   Prime and Provisions
   Address: 222 N LaSalle Dr, Chicago, IL 60601
8. The Berghoff
   A Chicago institution since 1898, The Berghoff serves authentic German cuisine and drinks, including its famous root beer.
   The Berghoff
   Address: 17 W Adams St, Chicago, IL 60603
9. Monk’s Pub
   Enjoy craft beer and classic pub fare at Monk’s, a Chicago staple known for its laid-back vibe and great drinks.
   Monk’s Pub
   Address: 205 W Lake St, Chicago, IL 60606
10. AceBounce
    If you’re looking for something fun, AceBounce is a Ping Pong bar where you can enjoy drinks, food, and some friendly competition.
    AceBounce
    Address: 230 N Michigan Ave, Chicago, IL 60601

Discover Chicago’s Loop with L Stop Tours

Now that you know where to eat, drink, and explore in Chicago’s Loop, why not experience it like a local? Book your tour with L Stop Tours and see the city from the comfort of the iconic L Train.

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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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