The Best 85 Things To Do in Chicago [2024]

Chicago, Illinois has been deemed the "Best Big City in the U.S." for six years in a row, helping it stand out as one of America's premier tourist destinations. The Windy City's world-class art and architecture, coupled with its delicious eateries, attract millions of visitors annually. Here, we'll discuss 85 of the best things to do in Chicago—and explore how AAA Travel can help you round out your itinerary.

Sightseeing and Landmarks in Chicago

Simply exploring and appreciating the Windy City’s unique landmarks is easily one of the best things to do in Chicago. Here are some ideas to get you started.

1. Navy Pier

Navy Pier is a blast from the past in the best way possible. Folks have visited this 1,010-meter pier since 1916, including the Navy Pier Auditorium—which is still one of Chicago’s top attractions over a century later.

2. Millennium Park

Millennium Park has been an integral part of Chicago’s atmosphere since it opened to the public in 2004. With 24.5 acres of open land, this public space is great for picnics, family outings and community events. It’s also one of the best places to run in Chicago.

3. The Bean (Cloud Gate)

Cloud Gate, colloquially known as The Bean, epitomizes Chicago’s unique art scene for several reasons. Anish Kapoor constructed this stainless steel sculpture in the mid-2000s. Since then, The Bean has appeared in numerous music videos by popular artists like Kanye West and Coldplay. A Chicago city tour wouldn’t be complete without a visit to this iconic art piece.

4. Willis Tower Skydeck

Willis Tower, formerly Sears Tower, was revered as the world’s tallest building for 25 years. Today, it’s still an instantly recognizable part of the Loop’s skyline—and a must-see on any Chicago architecture tour. Special mention goes to the Willis Tower Skydeck and the Ledge, a glass balcony overlooking the Windy City.

5. Chicago Riverwalk

Sights, sounds and scenery await you at the Chicago Riverwalk. This sprawling open-air space is great for daytime strolls and a night out with friends. The Riverwalk is also an excellent way to sample some of the food and culture that makes Chicago so remarkable.

6. Buckingham Fountain

Fans of Fox's classic sitcom, “Married... with Children,” will almost certainly recognize this architectural marvel. Buckingham Fountain is one of the world’s most incredible fountains, located on Chicago’s front yard. Buckingham Fountain was built in 1927 and received regular renovations. Best of all, you don't have to pay a cent to visit this landmark, which makes a trip to Buckingham Fountain one of the best free things to do in Chicago.

7. Grant Park

The size and scale of Grant Park are unlike anything else in the Windy City. This 319-acre urban park either houses or is close to many of Chicago's other famous attractions, like the Museum Campus and the Art Institute of Chicago. If you’re unsure what to do in Chicago, remember that Grant Park is an ideal destination for dog walking, jogging, picnics with the family or a romantic evening stroll.

8. Museum Campus

Museum Campus opened to the public in the early 20th century. Over the years, fantastic attractions have been added to the grounds, like the Adler Planetarium and the Shedd Aquarium. Visitors can expand their minds and stretch their legs across this 57-acre park.

9. Chicago Cultural Center

This historic venue opened in 1897 as the first public library in the city. Over the years, the Chicago Cultural Center became a premier destination for all things art. Visitors can enjoy free film screenings, concerts and cultural events annually. A trip to this venue is integral for any architecture, art and history tour in the Windy City. 

10. The Magnificent Mile

The Magnificent Mile is one of Chicago’s most eye-catching districts. There are skyscrapers, vintage buildings and more than 70 unique shops to visit. Travelers can also participate in special events like candle making classes from time to time.

11. 360 Chicago Observation Deck

The John Hancock Building is 100 stories tall and located within the Magnificent Mile. Ascend to the 94th floor, and you’ll find the 360 Chicago Observation Deck—a glass lookout that dangles 305 meters above the ground. If you sign up for a private Chicago architecture tour, there’s a good chance you’ll visit this iconic building.

12. Wrigley Field (Catch a Cubs game)

Baseball may be America’s favorite pastime, but it’s a cultural touchstone of major proportions in Chicago. Two renowned Major League Baseball (MLB) teams call Chi-Town home. One of them is the Chicago Cubs, and Wrigley Field is their stomping ground. Starting at $22, you can snag a ticket to a Cubs game, depending on demand. 

13. Guaranteed Rate Field (White Sox stadium)

We couldn’t talk about the Cubs without showing love to the White Sox. Originally known as Comiskey Park and later the U.S. Cellular Field, the Guaranteed Rate Field is a fully featured baseball park unlike any other. Special mention goes to the Xfinity Zone, the Home Plate Club and the Miller-Lite Landing.

14. Lincoln Park Zoo

Giraffes, skinks, chimpanzees, sloths and more await visitors at the Lincoln Park Zoo. This 35-acre zoo dates back to 1868, which pinpoints it as the fourth oldest zoo in North America. General admission to the Lincoln Park Zoo is free, though guests can sign up for guided tours and family-friendly experiences like the Lionel Train Adventure and a scavenger hunt.

15. Chicago River Cruise

If you're looking to embark on an urban adventure, signing up for a river cruise is one of the best things to do in Chicago. Sailing around the city will let you see dozens of iconic landmarks from a new perspective. 

Museums and Cultural Sites in Chicago

Chicago is an architectural hub and a major center for sustainable design. The following venues illustrate just how important art and architecture are in Chi-Town.

16. Art Institute of Chicago

World-class paintings and timeless sculptures await you at the Art Institute of Chicago. This premier venue displays over 300,000 works of art throughout the year. The institute can be overwhelming, so a private guided tour is never a bad idea.

17. Museum of Science and Industry

Innovation makes the world go round—and the Museum of Science and Industry is proof of that. Guests can explore a sprawling, 14-acre wide complex that showcases scale-model replicas of trains, airplanes and more!

18. Chicago History Museum

Established in 1856, the Chicago History Museum has been an integral part of the City of Big Shoulders for decades. Not only does this building house more than 23 million historic objects, but it also endured the Great Chicago Fire.

19. DuSable Black History Museum and Education Center

The DuSable Black History Museum and Education Center is a testament to the impact of Chicago’s Black community over the years. There are exhibits dedicated to Civil Rights leaders, the 1963 March on Washington for Jobs and Harold Washington—Chicago’s first Black mayor. Needless to say, the DuSable is a must-see on any African American Heritage Tour of Chicago.

20. National Museum of Mexican Art

In 1982, Carlos Tortolero collaborated with a coalition of Mexican-American teachers to establish the Mexican Fine Arts Center Museum. Over the years, that establishment evolved into the National Museum of Mexican Art—which houses one of the largest collections of Mexican art pieces in the world. 

21. Chicago Children's Museum

The Chicago Children’s Museum is a 3-story complex full of interactive exhibits and unique learning opportunities for kids. Rotating attractions mean there’s always something new for little ones to experience.

22. Museum of Contemporary Art

Contemporary art connects us with all sorts of distinct pieces, ranging from deceptively simple minimalist paintings to mind-bending avant-garde sculptures. The Museum of Contemporary Art Chicago showcases 2,700 art pieces and over 3,000 books.

23. International Museum of Surgical Science

The International Museum of Surgical Science is a reminder that medicine is an art form. Dr. Max Thorek established this facility in 1954, and it’s only evolved since then. Visitors can engage with paintings, sculptures, diagrams and medical texts divided by surgical discipline.

24. Chicago Cultural Center

What started as Chicago’s first public library eventually grew into one of the city’s most prominent attractions. The Chicago Cultural Center celebrates the city’s art, culture and architecture—and it’s an extremely popular wedding venue.

25. Chicago Design Museum

We can largely thank designers for the astonishing buildings and street art that make Chicago so special. The Chicago Design Museum started as a pop-up exhibit before earning a permanent place in the city in 2014.

Entertainment and Performances in Chicago

Whether you’re looking for a laugh or searching for orchestras and symphonies, Chicago’s entertainment and performing arts scenes always have something incredible to offer.

26. Broadway in Chicago

Broadway is far from Chicago, no matter how you slice it. Thankfully, the Broadway in Chicago touring company brings classic shows like Hamilton, MJ: The Musical, and Beetlejuice to the Windy City throughout the year.

27. Second City Comedy Club

The Second City Comedy Club is the stomping ground of legends like Amy Poehler, Bill Murray, Stephen Colbert and Tina Fey. Improv comedy is the name of the game for the most part, but the itinerary always has exciting acts.

28. Chicago Symphony Orchestra

You can find local conductors and guest artists from around the world at the Chicago Symphony Orchestra. Holiday Concerts also take center stage throughout the year, especially during Christmas time.

29. Chicago Theatre

Equal parts an architectural marvel and a historic landmark, the Chicago Theatre hearkens back to the roaring 20s. This dynamic entertainment space still hosts some of the best shows in the city, ranging from comedy specials to musical performances and everything in between.

30. Kingston Mines

If you really want an authentic Chicago nightlife experience, you have to visit Kingston Mines. This renowned blues club opened its doors in 1968 and has pleased countless music lovers since then.

31. ComedySportz Chicago

Someone got the crazy idea to mix improv comedy with a wicked selection of sporty activities. The result is ComedySportz Chicago, an interactive experience unlike any other.

32. The iO Theater 

The iO Theater, aka iO Chicago, isn’t just a great place to catch a comedy show—it’s an improv comedy training center that offers workshops, writing courses and five levels of improv classes.

33. Lyric Opera of Chicago

With roots stretching back to 1954, the Lyric Opera of Chicago is the Windy City’s premier destination for opera performances and opportunities to train with industry veterans.

Outdoor Activities in Chicago

Going for a stroll at golden hour is one of the best things to do in Chicago. Then again, the following venues are worth a visit regardless of the time of day.

34. Beaches along Lake Michigan

Lake Michigan is a sight for sore eyes—especially if you’ve flown into the city. Well, you can visit this gorgeous lake in person if you stop by any of the beaches scattered along the shore.

35. Bike along the Lakefront Trail

A bike tour in Chicago will almost certainly take you for a ride along the Lakefront Trail. Depending on the time of year, you might also have the chance to participate in a biking fundraiser.

36. Kayaking on the Chicago River

There are plenty of opportunities to hop on a Chicago River cruise—and just as many chances to go kayaking. You can rent equipment from a local shop or bring your own gear.

37. Lincoln Park Conservatory

A trip to the Lincoln Park Conservatory is an experience unlike any other in Chicago. This 3-acre conservatory was built in the 1800s, and the plants housed here have passed the test of time with vibrant colors. Special mention goes to seasonal exhibits like the Wildflower Walk and Lily Pool.

38. Millennium Park Summer Workouts

When the summer months roll in, Millennium Park becomes a hotspot for various physical activities. Yoga, pilates, kickboxing and Zumba classes are held on the Millennium Park Great Lawn on Saturdays from late May to early September.

39. 606 Trail 

The 606 Trail is built on the remnants of an old railway line. Also known as the Bloomingdale Trail, this 2.7-mile stretch is frequented by runners, joggers, dog walkers and cyclists.

Food and Dining in Chicago

A trip to the City of Big Shoulders just isn’t complete without trying out a few signature dishes. Here, we’ve outlined some of Chicago’s best dishes.

40. Local deep-dish pizza

One of Chicago’s signature foods is deep-dish pizza, especially if you can grab a slice from a local pizzeria. Giordano’s Famous Stuffed Pizza is one of the best places to eat iconic Chicagoan foods thanks to its unique approach to this classic dish.

41. Chicago-style hot dogs

Steamed poppy seed buns, all-beef franks and a mound of toppings are ingredients to the quintessential Chicago-style hot dog. Street vendors and food trucks throughout the city serve some of the tastiest dogs around.

42. Portillo's for iconic Chicago fast food

Portillo’s is a famous fast food chain that started in Chicago. Restaurants have opened across the United States, but it all started in Chicago. Special mention goes to their signature chocolate cake shake.

43. Taste authentic Italian food in Little Italy

Little Italy is the place to go if you want to sample authentic Italian food. Don’t forget to stop by one of the family-owned bakeries and grab some struffoli.

44. Explore diverse neighborhoods 

A tour through Chicago’s neighborhoods will illustrate just how much of a melting pot the Windy City is. Chinatown, Pilsen and Little Village will help you experience some of the various communities that make Chicago great. And you’ll get a chance to sample authentic cuisine from other cultures.

45. Garrett Popcorn Shops

Garrett Popcorn is a household name these days. Their roots stretch back to 1949, when the first location opened in downtown Chicago. 

46. Visit the Chicago French Market for gourmet treats

Travelers looking for a quick bite and grab-and-go meals should stop by the Chicago French Market. Though, you should be warned if you have a sweet tooth. After all, gourmet chocolate is something of a specialty here.

Shopping in Chicago

A souvenir is the perfect way to celebrate your adventures in Chicago. You’ll find tons of amazing mementos at the following venues—plus clothes, accessories and essential items. 

47. The Magnificent Mile for upscale shopping

One of the best things to do in Chicago is go on a Magnificent Mile shopping spree. With dozens of stores and unique boutiques, you’re sure to find a special souvenir to commemorate your trip.

48. Water Tower Place

This next entry is a vertical shopping complex named after a very special landmark. Water Tower Place boasts more than 100 stores for visitors to patronize, and it’s very close to the iconic Chicago Water Tower.

49. State Street Shopping District

Travelers will find a few familiar shops in the State Street Shopping District, like Macy’s, H&M and Nordstrom. While shopping, take some time to admire the architecture and scenery. After all, there are tons of striking skyscrapers in this area.

50. Andersonville for unique boutiques

Andersonville is one of Chicago’s historic districts, so many of its shops have an old-school aesthetic. The boutiques in this area are incredibly memorable and personal for that reason, selling inventory you can’t find anywhere else.

51. Wicker Park for hip and eclectic shops

There’s never a dull moment in Wicker Park. This neighborhood has a certain style and vibe that’s hard to describe with words. A quick visit to any of Wicker Park’s eccentric shops will get the point across in an instant. 

Parks and Recreation in Chicago

You don’t always have to break the bank to get the most out of a trip. One of the best things to do in Chicago is spend an afternoon at a local park.

52. Chicago Botanic Garden

City life can be great, but reconnecting with nature is never a bad idea. The Chicago Botanic Garden is the perfect respite from the hustle and bustle of the Windy City. Twenty-seven interconnected gardens spread across 385 acres means guests will have quite the nature walk ahead of them.

53. Northerly Island

Some of Chicago’s greatest attractions are repurposed structures. Northerly Island used to be an airport, but now, this 91-acre greenspace is a park, an event center and a concert venue.

54. Millennium Park Ice Skating

Old Man Winter transforms Millennium Park into a winter wonderland each year. When this happens, the Millennium Park Ice Rink opens to the public and entices guests to glide across the ice from November to March.

55. Maggie Daley Park

Chicago is always building new and exciting attractions throughout the city. Maggie Daley Park is one of the Second City’s younger attractions. It was built between 2012 and 2015 and is named after Maggie Daley—one of Chicago’s first ladies who valiantly battled cancer until 2011.

56. North Pond Nature Sanctuary

This 15-acre greenspace provides a refuge for the city’s wildlife and a place for city goers to unplug. Duck watchers will have a field day here, though you’re asked not to feed the wildlife.

Nightlife and Bars in Chicago

In Chicago, there are just as many great locations and experiences at night as during the day.

57. The J. Parker

Rooftop bars in Chicago capitalize on one of the city’s biggest draws—its unmistakable skyline. The J. Parker boasts New American cuisine, savory sips and a view visitors will never forget.

58. River North's nightlife scene

Art aficionados hold River North in high regard due to the sheer number of breathtaking murals scattered throughout the neighborhood. However, River North at night is just as artistic in its own way.  

59. Logan Square's trendy bars

Logan Square is a sight to behold during the day, but the nightlife in this neighborhood has to be experienced firsthand. This much can be said—if you like cocktail bars, you’ll simply adore Logan Square.

60. Piano bars and jazz clubs

Music is as much a part of Chicago’s identity as art, architecture and baseball. The cavalcade of piano bars and jazz clubs that spring to life at night can almost be overwhelming. Truly, a trip to one of these venues is essential to experiencing all of Chicago’s Events.

61. Experience a speakeasy like The Violet Hour

The Violet Hour is a vintage speakeasy that transports visitors back to the time before Prohibition swept the nation. With an award-winning bar and a knack for pre-prohibition drinks, the Violet Hour is a worthwhile trip for history lovers and cocktail connoisseurs. 

Cultural Festivals and Events in Chicago

Popular tourist attractions only reflect one aspect of any city. If you really want to know what Chicago is like, immerse yourself in some of the cultural events that pop up during the year.

62. Taste of Chicago

This 5-day food festival dates back to 1980 and is famous for being one of the largest festivals in the world. Deep-dish pizza, street tacos and funnel cake are always on the menu—and there are plenty of new delicacies to try out each year.

63. Chicago Jazz Festival

When Duke Ellington, a pioneer of Jazz and Swing, passed away in 1974, a Jazz Festival of grand proportions was held in his honor. Since then, the Jazz Institute of Chicago has held this event annually at Millennium Park.

64. Lollapalooza

Lollapalooza took the music world by storm in 1991. What started as a roving, four-day music festival of epic proportions soon became an iconic annual event in Chicago. Pearl Jam, Rage Against the Machine, Nine Inch Nails, Lady Gaga and Florence and the Machine have all graced the Lollapalooza stage.

65. Chicago Air and Water Show

Look up in the sky! It’s the Chicago Air and Water Show! Touted as one of the largest-scale free events in America, the Chicago Air and Water Show is an epic occasion that you won’t want to miss. For the best view, stop by the Lakefront. 

66. Chicago Blues Festival

Titans of the Blues genre, like Muddy Waters, Bo Diddley, Tampa Red and countless other artists, all have deep ties to Chicago. The Chicago Blues Festival became a staple of the “Second City” in 1984 and never fails to draw thousands of Blues lovers every June. 

Family-Friendly Activities in Chicago

Younger children and teenagers may grow restless if your itinerary isn’t well-rounded. Visit the following attractions to ensure the entire family has a great time.

67. Brookfield Zoo

Brookfield Zoo is about 13 and a half miles west of Chicago, but it’s worth the drive. At 216 acres wide, this is one of the most robust zoos in the country. Brookfield Zoo is a must-see if you’re looking to experience Chicago off the beaten path.

68. Sloomoo Institute

It’s always slime time at the Sloomoo Institute. This-one-of-a-kind attraction encourages families to take a break from their smartphones and engage with a vast array of slimy sensory experiences. 

69. Centennial Wheel

Centennial Wheel might have caught your eye while you were visiting some of the other attractions in this guide. That 200-foot Ferris wheel isn’t just for show. Snag your tickets and get an unparalleled view of Chicago with your family. 

70. Medieval Times Dinner & Tournament

If you love stories about brave knights, valiant steeds and breathtaking duels, you’ll love Medieval Times. Guests can watch live shows and eat freshly prepared food inspired by the Middle Ages.

71. Peggy Notebaert Nature Museum

Natural history museums can give us a glimpse into the distant past before the world was covered with so much infrastructure. The Peggy Notebaert Nature Museum is one of the oldest institutions in the city, and it lets visitors interact with Chicago’s native plants and animals.

Art and Galleries in Chicago

Amazing works of art are scattered all throughout the Windy City—you just have to know where to look.

72. Chicago Picasso 

The legendary Spanish artist Pablo Picasso created multiple masterpieces throughout his storied life. This untitled piece was one of his last creations, which he donated to Chicago in 1967. Now known as the Chicago Picasso, or sometimes just called “The Picasso,” this 50-foot steel sculpture is just as evocative as any of Picasso’s astonishing paintings.

73. 3rd Friday Gallery Walks in Pilsen

On the 3rd Friday of each month, a portion of the Pilsen neighborhood turns into an open-air art walk. Guests will be able to check out incredible artwork created by local artists.

74. Bridgeport Art Center

Artists and art appreciators are encouraged to visit the Bridgeport Art Center. Big draws include a sculpture garden, photo exhibitions and various art classes to bolster your brushwork and cement your ceramic skills.

Historical Sites in Chicago

History is being made every moment of every day, and there’s far too much to learn about the past in just one day. Still, a visit to these historical sites will get the ball rolling.

75. Chicago History Museum

Chicago's history is rich and nuanced. Dr. Martin Luther King spearheaded the Chicago Freedom Movement in 1965, and the Modern architecture movement is ingrained in Chicago's DNA. A trip to the Chicago History Museum can educate visitors on several key events in the City of Big Shoulders' development.

76. Robbie House

Frank Lloyd Wright was a revered and prolific architect who designed over 1,000 structures over 70 years. The Frederick C. Robie House is just one of his creations, and visitors can sign up for guided tours through this masterpiece.

77. Pullman National Historical Park

President Barack Obama designated this entry as a national park on February 19, 2016, due to its historic and cultural significance. Two railroad strikes occurred here throughout 1894. To this day, this venue remains an important landmark in the city of Chicago.

78. Jane Addams Hull-House Museum

Nobel Peace Prizes are often awarded to individuals who make incredible discoveries. Jane Addams became the first woman to earn a Nobel Peace Prize in 1931 due to her prolific career as a peace activist. The Jane Addams Hull-House Museum allows visitors to travel back in time and experience a day in her life.

Sports and Recreation in Chicago

An early morning jog or a late afternoon volleyball match might be just what you need after visiting some of Chicago’s busiest areas.

79. Participate in or watch the Chicago Marathon

Every October, the Chicago Marathon kicks off with a bang. This city-wide event has been held since 1905 and is one of six World Marathon Majors alongside Berlin, Boston, London, New York and Tokyo. Anyone who pays a $230/$240 fee can participate in this marathon, and you can always spectate for free.

80. Run or bike the Lakefront Trail

Here's another prime place to stretch your legs after a lengthy commute. The Lakefront Trail is 18.5 miles long and right beside Lake Michigan. Runners and cyclists adore this scenic space, and it’s integral to any bike tour of Chicago’s Lakefront Neighborhoods.

81. Play beach volleyball on the Lakefront

Where there are beaches, there are volleyball games. If you want proof of this fact, stop by any of the beaches sprinkled across the shore of Lake Michigan. And don’t forget to bring your sunscreen and your A-game.

82. Golf at Jackson Park

The city of Chicago cultivated Jackson Park to host the 1893 World Fair. This massive, 551.5-acre park houses many fantastic attractions, like the Museum of Science and Industry. It also sports an amazing golf course.

Educational Attractions in Chicago

Chicago wasn’t built in a day. Visiting the following venues is a great way to learn how the Windy City rose to prominence and who contributed to building it.

83. Chicago Architecture Center

Every building has a story. The Chicago Architecture Center provides a space where anyone can stop by and learn about some of the city’s most famous buildings. Visitors can also sign up for a river cruise aboard Chicago's First Lady.

84. Institute for the Study of Ancient Cultures Museum

Travel through the annals of time at this esteemed museum. The Institute for the Study of Ancient Cultures Museum (formerly the Oriental Institute) is located on the campus grounds of the University of Chicago. Admission costs $10 for adults and $5 for children.

85. Harold Washington Library

This learning center has roots that date back to 1897. Movie buffs may recognize this locale from Steven Soderbergh’s hit heist film Ocean’s Eleven (2001). Then again, the Harold Washington Library is a centerpiece on several Downtown Chicago TV & Movie Sites Tours.

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