Company Logo - Home Link

Things to Do in Downtown Chicago

What to Do in The Loop

Updated: September 18, 2023
 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!

To write this post, I relied on the extensive experiences that I and my fellow local tour guides have of SoHo.

We lead dozens of guided walking tours through the streets of the Loop every week, guiding hundreds of visitors each week.

We know a thing or two about this place. We even wrote and published an audio tour of the area.

Listen to a sample of our Downtown Chicago Tour, written and recorded by one of our tour guides.


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.  

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, read our guide to using public transit.

And if you are driving in, a good parking lot is the 60 East Lake Street parking garage.


There are a number of things to do in and around the Loop. Below are a few suggestions.

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, now the Chicago Cultural Center. 

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

To learn about the Chicago Cultural Center, join us on our seasonal Pedway Tour or Holiday Tour.

Hop onto our Birth of the Skyscraper-Architecture Tour to learn more about the current Chicago Public Library.

It also covers well-known Windy City landmarks in Grant Park such as the Willis Tower (formerly the Sears Tower) and visits Buckingham Fountain.

You'll also see some of the buildings on our Chicago Riverwalk and History Tour which talks about locations such as The Chicago Theater, The Wrigley Building, and The Chicago Tribune Building

The Magnificent Mile Tour takes guests past notable buildings such as The Tribune Tower, The John Hancock Building, and The Wrigley Building.

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.

If you want to try that you might like our Downtown Self-Guided Tour.

You might also enjoy the Chicago Architecture Center (the CAC) which offers programs and presentations that display the architectural legacy of Chicago, as well as its ongoing innovations in this field.

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 tamer, 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 Willis Tower Skydeck which is on the 103rd floor at 1353 feet (412.2 meters).

You will see a spectacular view of the Chicago skyline and Lake Michigan.  

Our post on observation decks in the Chicago area will give you information on a few different places for a great view.

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 Millennium Park, there are many lovely gardens and several pieces of notable public art; the 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 is 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)

Note that just across from Millennium Park is the famous Chicago bull statue, near the corner of N. Michigan Avenue and Washington St.

5. Enjoy Events at Pritzker Pavilion

During the summer months, the Pritzker Pavilion is an active hub of music, dance, and special events.

The best part is that all of the events are free!  

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

6. Visit the Art Institute

The Art Institute of 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 peer onto Monet’s haystacks, Van Gogh’s self-portraits, and Seurat’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.

For information on ticket discounts, read our post: Art Institute Tickets and Discounts.

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!

7. Discover Public Art

The art in Chicago isn't always in museums - though Chicago has a great art museum centrally located near the Loop.

However, much of what you can find in the city is public art.

No entry fee, no docent - in fact, no walls. They are outside in parks and plazas!

Our post, Public Art in Chicago covers some of the works below in more detail.

  • The Flamingo: designed by Alexander Calder 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 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, this sculpture is 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. Stop In At Marshall Field’s

To visit a truly iconic Chicago establishment, you’ll need to visit the old Marshall Field 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. 

This was the first restaurant opened in a department store.

After lunch, if you explore the 7th floor, you will see a wall of history about Marshall Fields.

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 boasts 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. Visit the Museum Campus and Other Loop Museums

Museum Campus Chicago is a 57-acre green oasis on the lakefront situated at the south end of Grant Park.

The campus was first imagined back in 1909 and has grown since, bringing a number of art institutions closer together while also providing a shared area where folks can gather.

Today you'll find the Field Museum of Natural History, the Shedd Aquarium, and the Adler Planetarium, along with Solder Field, McCormick Place Bird Sanctuary, Northerly Island, and McCormick Lakeside Center.

For discounts and free days, read our posts on:

The American Writers Museum is another Loop option for anyone who loves literature.

Head to the Money Museum if you are fascinated by old bills and the process of printing money.

The Museum of Contemporary Photography has an impressive range of collections and exhibitions from contemporary photographers as well as emerging and established artists.

With more than 30,000 photographs, including works by renowned names such as Diane Arbus, Walker Evans, and Robert Frank, the Museum of Contemporary Photography is nothing short of a treasure trove!

10. Relax in 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- is across the street and is magnificent.  Check out their free “Chapel in the Sky” tour Tuesdays-Saturdays at 2 pm. 
  • 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. Take in Some Shopping and Food

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

Michigan Ave. is arguably downtown Chicago's most famous street.

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 which 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 foods 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.

Iconic Chicago:

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

Budget Eats:

Indulgent Meals:

Unique Places:

  • Revival Food Hall: 125 S Clark | over 15 local eateries in one convenient and gorgeous location

12. Visit Navy Pier

Chicago's Navy Pier, lovingly called the "People's Pier," has certainly come a long way since it was originally constructed in 1914 as the world’s largest pier at 292 feet wide and 3000 feet long (89m x 914m). 

Navy Pier (originally called Municipal Pier #2) was built for shipping and entertainment.

Today, it is a cultural hub for locals and visitors of Chicago to explore unique dining, free and paid arts and entertainment attractions, and popular cultural exhibits

This is a great place to take kids as they're sure to enjoy the Centennial Wheel, a giant Farris wheel.

The Chicago Children's Museum is also there.

For more ideas of things to do, read our post 16 Top Things to Do at Navy Pier.

13. Enjoy Chicago Entertainment

Chicago is known for its comedy! Some of the best comedians came out of the Windy City; Bill Murray, Amy Pohler, Tina Fey, and Chris Farley, to name a few.  

During the chilly nights of March, a good laugh will be sure to warm you up. 

Check out Second City for sketch comedy, stand-up, and improv. 

Another local favorite is i.O. which is improv and sketch, and you can head to the Laugh Factory for stand-up.

You might visit the United Center for all sorts of events, from music to sports (the Bulls and Blackhawks play here).

Find tickets to United Center events here.

Stroll (run, bike) the Lakefront Trail.

This 18-mile trail runs along the western coast of Lake Michigan and is a favorite for walkers, runners, and those with bikes.

Best of all it's free. For more free things to do in Chicago, read our post.

The Lincoln Park Zoo is one of the oldest zoos in the country, and one of the last few free zoos.

With over 1,000 animals to see, kids are sure to enjoy it. Read our post Things to Do at the Lincoln Park Zoo.

14. Visit the Water Tower

As one of the oldest structures in Chicago's Loop area, the iconic Water Tower stands on North Michigan Avenue on the Magnificent Mile.

Originally built in 1869 to house a water pump that supplied nearby citizens with water, it was one of few buildings able to withstand the Great Chicago Fire of 1871.

Its significant role during this disaster - aiding firefighters in putting out raging flames - has made it a symbol of the city's strength and resilience.

The tower stands 154 feet tall with a square structure made entirely of limestone and features Gothic-style architectural elements.

It is listed on the National Register of Historic Places and has been used in a variety of ways, including as a public library branch and office for the renowned Chicago Park District.

Today there is an art gallery inside, City Gallery, which features photos of Chicago by photographers from the city.


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%.

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: September 18th, 2023
Back to Top