Best places to visit in Chicago: top attractions you don't want to miss

They don't call it the Mecca of the Midwest for nothing. Illinois' largest city is also home to some of the country's most important sights. From must-visit Chicago landmarks and monuments to incredible art museums, the Windy City rewards visitors of all tastes. Get ahead of your trip with these 20 must-see attractions, covering everything from Al Capone's HQ and the Magnificent Mile to the world-famous Art Institute of Chicago.

As the birthplace of the skyscraper, every Chicago itinerary must include a close look at the city’s architecture too. You can explore the iconic skyline at the John Hancock Building or ascend the Willis Tower for a bird’s-eye view. Visiting Chi-town with kids? The Museum of Ice Cream will be the highlight of their vacation. Whatever you pick, you can't go wrong with this list of Chicago’s best places to visit.

Best places in Chicago for history

1. Al Capone's HQ

A Gangsters and Ghosts walking tour is probably not the first thing that comes to mind when you think of family-friendly activities. However, this 1.5-mile, 2-hour long, historian-guided walk to Al Capone's HQ is suitable for most age groups. Other sites of interest include speakeasies, secret tunnels, and haunted buildings. Learn all about Chicago's 20th-century underbelly.

Highlights:

Learn about the infamous Loop, see how Capone ran his empire, visit haunted sites, and hear ghost stories.

Address and opening hours:

Meet outside the Wyndham Hotel at 71 E Wacker Dr, Chicago. Tour dates and times vary.

2. Medieval Torture Museum

Not for the underaged or the faint of heart, the Medieval Torture Museum takes you through one of the darkest eras in human history and perhaps the most macabre side of humanity. Its interactive experience features life-like wax sculptures of executioners and their victims, an audio guide, and a ghost-hunting app. Explore the 5,000-square-foot exhibition of exhibits depicting torture, interrogation, restraint, and execution techniques and devices.

Highlights:

Immersive audio-guided experience with realistic wax sculptures.

Address and opening hours:

177 N State St, Chicago. Open Monday-Thursday, 10:00 AM-8:00 PM, and Friday-Sunday, 10:00 AM-9:00 PM.

3. Simon’s Tavern

Travel back in time, a century or so ago, to the Prohibition Era with a speakeasy tour of Chicago. This 3-hour VIP experience takes you from chauffeured luxury cars to bars like Simon’s Tavern, via undisclosed access points. Sample the drinks that infamous gangsters would have had in the 1920s and listen to a historian's account of the type of racketeering, bootlegging, and other shenanigans from back in the day.

Highlights:

Travel in style, hear Prohibition stories from a well-versed historian, and experience the danger and mystery of clandestine speakeasies.

Address and opening hours:

Location kept under wraps. Available daily throughout the year with hourly slots, 4:00 PM-9:00 PM.

4. Chicago History Museum

Go back to the city's roots at the Chicago History Museum. There are over 20 million items, including photos, documents, and artifacts with interactive displays. Feel the heat of the Great Chicago Fire, get lost in the crowds on Maxwell Street, and hover over the city on an L-beam at Sears Tower.

Highlights:

See Chicago's first L train passenger car, fashion through the ages with the Marshall Field's window display, and take a selfie in a hot dog bed.

Address and opening hours:

1601 N Clark St, Chicago, IL. Tour dates and times vary.

5. Field Museum of Natural History

Learn about ancient civilizations and prehistoric creatures at the Field Museum of Natural History. See magnificent gemstones and peculiar subterranean lifeforms, the mammoth hunters of the Ice Age, and the temples of the Incas and the Aztecs.

Highlights:

Discover the world's largest and most complete T-Rex skeleton, the largest blue topaz, and the Mastaba tomb complex.

Address and opening hours:

1400 S Lake Shore Dr, Chicago, IL, 60605. Open Monday-Sunday, 9:00 AM-5:00 PM.

Best places in Chicago for art

6. Art Institute of Chicago

Experience art with a visit to the Art Institute of Chicago. View ornate furniture, masks, fashion items, and ancient artifacts. Gaze at stained glass, architectural carvings, ornate headdresses, Japanese prints, and intricate sculptures.

Highlights:

See the works of European greats like Monet and Van Gogh. Explore Greek, Roman, Byzantine, African, Egyptian, Aztec, Renaissance, and Medieval art.

Address and opening hours:

S Michigan Avenue, Chicago, IL, 60603. Open Monday and Friday-Sunday, 11:00 AM-5:00 PM, and Thursday, 11:00 AM-8:00 PM.

7. American Writers Museum

Find out about the history of writing at the American Writers Museum. Learn about the intricacies of language and the art of creative writing.

Highlights:

Use a vintage typewriter and discover American writers, from Poe to Prince.

Address and opening hours:

Crain Communications Building, Chicago, IL, 60601. Open Monday and Thursday-Saturday, 10:00 AM-5:00 PM, and Sunday, 10:00 AM-3:00 PM.

8. Logan Square

To get a feel for urban art in Chicago, book a guided street art tour and learn to see the city as a living canvas. Roaming through Logan Square, Wicker Park, and other neighbors with a thriving street art scene.

Highlights:

Learn about today's top artists, the stories behind their works, how masterpieces reflect local culture, and watch street artists at work.

Address and opening hours:

Meet at The Goddess and Grocer, N Damen Ave, Chicago, IL 60647. Available Monday, Friday, and Sunday, 10:00 AM and 1:00 PM, and Saturday, 10:00 AM.

9. Chicago Cultural Center

The Treasures of the Golden Age walking tour brings you face-to-face with the city's revival masterpieces. Take in the splendor of the Beaux Arts and the Neo-Gothic style.

Highlights:

Peek inside some of the ritziest buildings in the world, including the Chicago Cultural Center, Macy’s on State, and the Palmer House Hotel.

Address and opening hours:

Meeting point inside the CAC at 111 E Wacker Dr, Chicago, IL, 60601. Tours are available at 10:30 AM and 2:00 PM.

10. Carbide and Carbon Building

The business boom of the '20s brought the Parisian Art Deco style to Chicago with masterful architecture like the Carbide and Carbon Building. An Art Deco skyscrapers tour reveals how Cubism and Middle Eastern art came together in this style.

Highlights:

Experience Art Deco motifs first-hand and learn their origins, view the opulent interiors of 5 Art Deco skyscrapers, and identify Art Deco motifs on skyscrapers with the help of a CAC-trained expert.

Address and opening hours:

30 N La Salle St, Chicago, IL 60602. Tours available Wednesdays at 1:30 PM and Sundays at 2:00 PM.

Best places in Chicago for families

11. Museum of Illusions

Prepare for an otherworldly experience at the Museum of Illusions. Marvel at some of the world's most mind-bending holograms, optical illusions, and gravity-defying attractions.

Highlights:

Change in size from one immersive room to the next, Alice in Wonderland style, and take a headscratcher of a snap at one of the best places to visit in Chicago.

Address and opening hours:

Chicago Loop, Chicago. Open daily, 10:00 AM-8:00 PM.

12. Museum of Ice Cream

Located inside the Chicago's landmark Tribune Tower, the Museum of Ice Cream is a selfie museum, and everything's about you and your sweet tooth. Make your own edible glitter or slime. Eat as much ice cream as you like. Learn all there is to know about the icy treat.

Highlights:

Plunge in the world's most Instagrammable sprinkle pool and ride the pink Sprink-L line to your heart's content.

Address and opening hours:

Tribune Tower, 435 N Michigan Ave Suite G, Chicago. Open Wednesday-Monday at varying times.

13. iFLY Lincoln Park

Try an indoor skydiving experience at iFLY Chicago Lincoln Park. There's no need to worry about motion sickness, nausea, or a knot in your stomach here. Fly for 60 seconds together in complete and utter bliss. There's no jumping or falling, but there's plenty of fun to be had as you float in this safe but ultra-powerful wind tunnel.

Highlights:

Freefall in safety and under instructor supervision. Enjoy adrenaline-inducing skydiving.

Address and opening hours:

800 W Scott St, Chicago, IL. Open Wednesday-Sunday, at varying times.

14. John Hancock Building

Be tilted in the air as you're leaning on a glass screen over the city of Chicago on the 94th floor of the John Hancock Building. The 360 Chicago Observation Deck offers you the most amazing view of the waterfront and 4 neighboring states.

Highlights:

Go from 0 to 1,000 feet high in seconds in one of the fastest elevators in the USA. Use the Magnicity App for a self-paced guided tour, experience incredible views, and learn about the city's history.

Address and opening hours:

875 N Michigan Ave 94th floor, Chicago. Open Monday-Sunday, 9:00 AM-11:00 PM.

15. Willis Tower

Get high at The Ledge on the 103rd floor of the Willis Tower Skydeck. Imagine seeing the whole of Chicago through a single pane of glass. Feel on top of the world in your glass-paneled box for a full 2 minutes.

Highlights:

Learn about the tower's history. Enjoy the Skydeck app with the viewfinder and free Wi-Fi.

Address and opening hours:

Willis Tower, Chicago, IL, 60606. Open Monday-Sunday, 9:00 AM-10:00 PM.

Best places in Chicago for culture

16. Navy Pier

Visiting Navy Pier is one of the best fun things to do in Chicago. A fireworks cruise by Navy Pier is where pyrotechnics flicker in the night sky. There are several viewing options and cruise lengths to choose from. Take in the view on a cruise, then explore the pier on foot to enjoy attractions, dinning, and shops.

Highlights:

Admire the skyline, the architecture, and the city lights, enjoy locally sourced food and beverages, and experience a laid-back night out on the town.

Address and opening hours:

Tickets and bags checked at the foot of the Wrigley Building at 400-410 Michigan Ave, Chicago. Late May-early September, at 8:15 PM on Wednesdays and at 8:30 PM on Saturdays.

17. Chicago's Lakefront

Enjoy exploring with a Lakefront and museum campus Segway tour. Roam across 8 miles of Chicago's Lakefront, seeing many of its best tourist attractions first-hand and learning about its history, all in around two hours.

Highlights:

Gliding across Grant Park, whizzing past the Bean, and circling Buckingham Fountain's water show is a great way to experience the city.

Address and opening hours:

300 E Monroe St, Chicago. Available most days at 12:30 PM.

18. Magnificent Mile

Experience the best bites in Chicago on a guided walking and tasting tour  along the Millennium Walk and Magnificent Mile. Gaze at the city's most iconic buildings and take in the grandiose architecture on a 2.5-hour leisurely walk with pit stops for street food, pizza, and brownies.

Highlights:

Dive into that deep-dish pizza, grab a Chicago hot dog, savor an Italian beef sandwich, and try an original recipe brownie — eat all the best food in Chicago. Tours run in any weather, either at street level or via Pedway underground.

Address and opening hours:

Meet at 410 N Michigan Ave, Chicago. Available daily at 11:30 AM; occasionally, also at 11:00 AM.

19. Wrigley Field

Grab a ticket to a Chicago Cubs baseball game and experience Chicago's favorite pastime. Wear the old red and blue at Wrigley Field, home of the Cubs for over a century.

Highlights:

Cheer on the Cubs at the iconic Wrigley Field, experience a thrilling Major League Baseball game, and watch some of the best players in history.

Address and opening hours:

1060 W Addison St, Chicago, IL 60613. Available on various days and times.

20. Chicago Architecture Center

See how local architects are changing the world's skyline at the Chicago Architecture Center. Known locally as the CAC, it showcases the city's iconic buildings, such as the Tribune Tower and the Wrigley Building, via 40-foot-tall glass panes. Also, learn about the city's rise from the ashes of the Great Chicago Fire. Get a feel for the thrill of the city's race to the top as you behold the world's first skyscraper, now dwarfed by the Sears Tower.

Highlights:

City Model Experience with 4,200 buildings, models of famous skyscrapers from around the world, and exhibits of local house styles and architects.

Address and opening hours:

111 E Wacker Dr, Chicago, IL, 60601. Open daily 10:00 AM-5:00 PM.

FAQs

How many days should I spend in Chicago?

To get as much out of your city break as possible, consider spending at least three days in the city.

What is the best time of year to visit Chicago?

The best time to visit in terms of weather is April to May or September to October. The crowds are manageable, the parks are at their best, and the festivals are in full swing at these times.

How do I get around Chicago?

Chicago is best explored on foot, though tourists often prefer public transportation and the L train. The city also has a bustling cab community and low-cost transportation networks like Uber and Lyft. Other options include the water taxi, limo services, driving, and biking through the bike-share program.

What are the best neighborhoods to visit in Chicago?

Some of the best-loved neighborhoods include South Shore, West Ridge, and Albany Park. To immerse yourself in Puerto Rican culture, head over to Humboldt Park. To witness the living monument that is the city's "Black Metropolis," go to Bronzeville. To experience the nightlife, head to Uptown. For a taste of the high life, explore the Gold Coast.

What are the best places to go shopping in Chicago?

Chicago is a shopper's paradise. For a whirlwind shopping spree and an improv show after a day of sightseeing, try Woodfield Mall. For a more ethnic experience, try Andersonville, the city's traditionally Swedish hotspot. Alternatively, immerse yourself in luxury at River North, the city's premier shopping area near Michigan Avenue.