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Things to Do in Chicago’s Loop

Updated: October 12, 2021
 By Mel

This post will cover some of the most interesting things to do and see while visiting Chicago’s Loop neighborhood. 

Since the Loop is a vibrant community of work and play, every traveler will find something that suits their tastes!




The name derives from the circle or “loop” that the cable cars in the 1800s made in this area and currently the elevated trains run along the same circular path.  

To learn more about this neighborhood and the rich history that takes place here, we have several Pay-What-You-Like tours that will appeal to every traveler. 

Check out the Loop & Millennium Park Tour that explores the northern section or our Birth of the Skyscraper-Architecture Tour which delves into the history of our buildings or enjoy the West Loop Gateway Tour that ends at one of the only buildings that survived the Great Fire.

Alternatively, you can also get here using a hop-on-hop-off bus tour.  All bus companies have multiple stops in the Loop.

You can reach this area easily by using Chicago’s Public transit.  If you are new to Chicago, then take a read of our guide to using public transit.


1. Explore the Architecture

While many visitors will stroll along the Riverwalk or take a boat tour to get their Chicago Architecture views- many of the architectural gems are hidden right in the Loop!  

One example of a great building that also has free events is the current Chicago Public Library and the past Chicago Public Library which is now the Cultural Center. 

Both of the buildings are extraordinary and both have free programming!

To learn more about the current public library, hop onto our Birth of the Skyscraper-Architecture Tour.  To learn about the Cultural Center, join us on our seasonal Pedway Tour or Holiday Tour.

Another great option is to try our Downtown Self-Guided Tour.

The best way to appreciate this living history of buildings is on our architecture tour but roaming on your own is still a perfect way to spend an afternoon.

2. Check out the Theatre District or Movies

The Loop was originally an area of old movie palaces, vaudeville acts, and jazz clubs. 

Today it is a bit more tame, but still famous for a few iconic movie palaces turned into concert or theatre venues.

Theatres in the Loop area include:

If you are a film-lover, visit the Gene Siskel Film Center to catch film festivals, independent films, student films, foreign films, and art films.  It is located at 164 N. State Street.  

If you’d like to catch the best big blockbuster, head to the AMC Movie Theatre at the Block 37 Mall.  You can watch the next big hit while in a recliner and eating your dinner.

Pro-tip: Check out our self-guided Downtown Chicago Theatre Tour if you love theatre buildings.  Of course, Chicago theatre is not limited to this one neighborhood and we encourage all visitors to travel outside of the Loop!  

To see a full calendar of all shows or to buy tickets for shows, click here.

3. Visit the Tallest Building in Chicago

The Willis Tower (known as the Sear Tower to locals) was the tallest building in the world from 1973-1998 standing at 442 meters (1.450 ft) with 110 floors. 

While it isn’t the tallest in the world anymore, Chicago is still fiercely proud of the Skidmore, Owings, and Merrill Building! 

If you aren’t afraid of heights, check out the observation deck which is on the 103rd floor at 1353 feet (412.2 meters) You will see a spectacular view of Chicago and Lake Michigan.  

For a unique experience, step out onto the “Ledge”, an included attraction where you can stand directly over the street!  

4. Visit Millennium Park & Cloud Gate

While a bit outside of the official Loop, Millennium Park is still considered a part of the Loop neighborhood. This park was built to celebrate the turn of the century and opened in 2005.   

Inside of Millennium Park, there are many lovely gardens and several pieces of notable public art; most recognizable is “Cloud Gate” which is more commonly referred to as “the Bean”.

This stainless steel reflective piece by Anish Kapoor is the centerpiece of Millennium Park.  Learn more about it on our Loop & Millennium Park Tour.

Things to see  in Millennium Park:

  • Cloud Gate designed by Anish Kapoor
  • Pritzker Pavilion designed by Frank Gehry
  • Crown Fountain designed by Jaume Plensa
  • Lurie Garden- a 5-acre garden that pays homage to our city motto “The City in the Garden”
  • Wrigley Square and Millennium Monument (Peristyle) to honor the Millennium Park Founder’s
  • The rotating Boeing Galleries- Constantly changing public art
  • BP Bridge designed by Frank Gehry (which heads to Maggie Daley Park)
  • Nichols Bridgeway designed by Renzo Piano (which heads to the Art Institute’s Modern Wing)

5. Pritzker Pavilion

During the summer months, Pritzker Pavilion is an active hub of music, dance, and special events. The best part is that all of the events are free!  

Mondays & Thursdays: Enjoy concerts in the park with their summer music series.

Tuesdays: You can watch movies in the park at their summer film series. 

Tuesdays & Thursdays: There are early morning fitness classes with the summer work-out series.

During the winter months, it is still a lovely destination because you can appreciate the incredibly artistic structure designed by famed Frank Gehry himself.

6. Visit the Art Institute

The Art Institute in Chicago which was founded in 1879 is one of the oldest and largest art museums in the United States.

Travelers from all over the world visit to peer onto Monet’s haystacks, Van Gogh’s self-portraits, and Serat’s “Sunday in the Park.”  

Inside the Art Institute you will find a unique Chicago treat- the Louis Sullivan original trading room from the original Board of Trade reassembled. 

Also, behind the Art Institute is an original stock exchange arch design by Adler and Sullivan.

Pro Tip:  hop-on-hop-off bus tours  stop right outside of the Art Institute!

Fun Fact:  The Art Institute is technically the location of the start of Route 66!  Be sure to find the Route 66 start sign!

Tour Group at Route 66 Chicago

7. Discover Public Art

If you’d prefer to experience public art, there is plenty of that in the Loop as well.  

  • The Flamingo designed by Alexander Calder (pictured above) can be found at 50 W. Adams St.
  • Chicago’s Miro designed by Miro is located across from Daley Plaza at 69 W. Washington St.
  • Four Seasons designed by Marc Chagall (pictured below) can be found at 10 S. Dearborn St.
  • Monument with Standing Beast designed by Jean Dubuffet is located at 100 W. Randolph St. in front of the Thompson Center
  • Chicago’s Picasso designed by Pablo Picasso in Daley Plaza at 50 W. Washington St.
  • Lions at the Art Institute by Kemley are in front of the Art Institute at 111 S. Michigan Ave.
  • Crown Fountain designed by Jaume Plensa in Millennium Park at 201 E. Randolph St.
  • Cloud Gate by Anish Kapoor in Millennium Park at 201 E. Randolph St.

More recently, Chicago has started an exciting mural project in the Loop as well! 

Check here for details about the Wabash Arts Corridor. 

More and more we are finding updated street art in the Loop, like the Muddy Waters mural memorializing the famed blues musician at 17 N. State St. by Kobra.

8. Marshall Field’s

To visit a truly iconic Chicago establishment, you’ll need to visit the old Marshall Field’s building which is now the Macy’s on State street.  

Architecturally, this building is a delight, but it is the inside that counts.  There is an incredible Tiffany Glass ceiling above cosmetics that will delight every traveler passing through.  

Looking for a perfect lunch destination?  Head to the 7th Floor for the famous Walnut Room. 

Walnut Room Chicago

After lunch if you explore the 7th floor, you will happen upon a wall of history about Marshall Field’s. The history of this building is quite interesting and is told on our Loop & Millennium Park tour.  

If you have time to wander, go to the basement which boast a tasty candy shop to sample Marshall Field’s Frango Mints. 

You’ll also find a very affordable cafeteria-style lunch destination in the basement if you find yourself needing a snack.  When you are ready to leave, wander out through the Pedway through the stained glass museum.  

9. The Cultural Center & Museums

Whether you enter the Cultural Center from the street or through the Pedway System on your own or with our Pedway Tour group- it is an architectural gem. 

Exterior of Chicago Culture Center

The building itself was originally Chicago’s Public library and shows its love for literature through etched quotes on the walls.

The Cultural Center is a free public art museum and event center.  Be sure to check out their event schedule as well as their free guided tour schedule.

The American Writers Museum is another Loop option for anyone who loves literature or head to the Money Museum if you are fascinated by old bills and the process of printing money.

10. Daley Plaza

The Daley Plaza in Chicago is a great place to meet locals! It is a public square that is the home to the Picasso Statue which was a gift from Pablo Picasso. 

It is the perfect place to enjoy local coffee while pigeon watching or to catch a special event.  

While you are in Daley Plaza, things to look for in the plaza or nearby include: 

  • The Veteran’s Memorial - Next to the Picasso
  • Miro’s Chicago statue across the street
  • The First United Methodist Church- Across the street and magnificent.  Check out their free “Chapel in the Sky” tour Tuesdays-Saturdays at 2pm. 
  • City Hall- An incredible building inside and out designed by Holabird and Roche
  • The Daley Center built in 1965

Pro-Tip: Since the Loop is such a central area- there are often parades downtown- often marching right past Daley Plaza.  Be sure to check out the parade schedule here.

11. Shopping and Food

The Loop is known for the shopping along State Street and the tourist shops on Michigan Avenue. 

State Street is considered the shopping district of the Loop and is loaded with more discount shopping (unlike the Magnificent Mile with designer brands).  

Chicago Tourist Shop

You’ll find shops like Macy’s, H & M, Old Navy, Nordstrom Rack, and Urban Outfitters. 

The largest mall in the area is Block 37 and has shops like the Disney Store, Zara, and a custom tennis shoe store.

As for food, the Loop has many delicious options for visitors who love to travel through food!  

Of course, the most famous Chicago Food are: Pizza, Hotdogs, and Italian Beef Sandwiches, but Chicago is a food city and we pride ourselves on options! 

See below for just a sampling of food choices in the Loop area.

Chicago Hot Dog

Iconic Chicago:

  • Al’s Beef at 169 W Ontario St - Best known for their Chicago Hot Dog and Italian Beef Sandwich
  • Italian Village at 71 W Monroe St - The oldest restaurant in the Loop
  • Billy Goat Tavern at 60 E Lake St - While not the original location, still quite tasty!
  • Bergoff’s at 17 W Adams St - German restaurant that has the first liquor license after prohibition
  • The Walnut Room at 111 N State St- Beautiful and historic restaurant on the 7th floor of Macy’s
  • Pizano’s at 61 E Madison St - Thin crust and deep dish pizza
  • Giordano’s at 223 W Jackson Blvd - Thin crust and deep dish pizza
  • Garrett’s Popcorn- several locations! - Chicago’s official snack food

Budget Eats:

  • Head to the Thompson Center at 100 W Randolph for a giant American food court
  • Taco Bell at 178 N Wabash- One of the first to ever serve alcohol
  • Jason’s Deli at 195 N Dearborn - Healthy choices and comfort foods
  • Potbelly- several locations! Chicagoland local chain sandwich shop

Indulgent Meals:

  • Petterinos at 150 N Dearborn- Delicious Italian food with music on Mondays
  • Rose Bud at 70 W Madison- Great date location with steak and pasta
  • The Dearborn at 145 N Dearborn- Chic American dining
  • The Chicago Athletic Association at 12 S Michigan Ave- Amazing view and amazing meals
  • Catch 35 at 35 W Wacker- High end seafood

Unique Places:

  • Revival Food Hall at 125 S Clark - over 15 local eateries all in one convenient and gorgeous location
  • Heaven on 7 at 111 N Wabash- A Nola style restaurant with gumbo and the works. (Cash only!)
  • Latinicity at 108 N State St - tasty Latin inspired dishes on the top of Block 37 mall

Chicago City Pass

While most of the things in the Loop aren’t on the Chicago City Pass- a few are! Many of Chicago’s biggest attractions have entry fees.

While you do pay for a tourist discount pass, it can give you a bulk discount and free admission into some interesting tours and museums, saving you up to 55%.


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They can also save you time with skip-the-ticket-line privileges.

Each Chicago Tourist Discount Pass includes a variety of fun family-friendly activities and attractions.

Here are a few examples of what you can visit with a tourist pass, for a discount or for free.

For more details, make sure to read our full post covering Chicago tourist passes.


About The Author


Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
Updated: October 12th, 2021
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