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The 20 Best Things To Do in Chicago

Chicago is one of America’s most iconic cities. Known for its stunning architecture, impressive museums, vibrant music scene, delicious food, and lakefront parks – the Windy City has something for everyone. If you’re planning a trip to Chicago, these are the best things to do to experience this amazing city.

1. Take an Architecture Boat Tour on the Chicago River

One of the best ways to see Chicago’s world-famous architecture is from the river. Architecture boat tours glide along the main branch of the Chicago River through the heart of downtown. Knowledgeable guides will point out the most iconic skyscrapers and explain the history and design elements of each.

You’ll float by the Willis Tower, once the tallest building in the world. Gaze up at the art-deco Chicago Tribune and Wrigley Building with its iconic clock tower. Marvel at the corncob-shaped towers of Marina City. And learn how ingenious Chicago architects led the way in developing steel frame construction and gave birth to the modern skyscraper.

Most boat tours last 75-90 minutes. Popular companies include Shoreline Sightseeing Cruises, the Chicago Architecture Center River Cruise, and Wendella Boats Chicago Architecture Tour. Tours run daily throughout the year with enclosed and open-deck seating available. Don’t forget your camera!

2. Stroll and Shop the Magnificent Mile

The Magnificent Mile is Chicago’s most famous shopping district. This 13-block stretch of North Michigan Avenue runs from the Chicago River north to Oak Street. Here you’ll find hundreds of big-name stores, luxury brands, fancy hotels, and national retailers.

High-end shopping abounds at department stores Bloomingdale’s, Nordstrom, Neiman Marcus and Saks Fifth Avenue. Check out the massive flagship American Girl Place store. Or pop into unique boutiques for cutting-edge fashion, home goods and souvenirs.

Don’t miss Water Tower Place, a 8-level shopping mall with 120 stores and restaurants. Grab a snack in their large Food Court. And be sure to gaze up at the building – it’s one of the earliest vertical malls ever built!

3. See “The Bean” at Millennium Park

Millennium Park is a dazzling centerpiece of downtown Chicago. The park’s iconic centerpiece sculpture is Cloud Gate, affectionately nicknamed “The Bean”. It’s a giant reflective steel structure shaped like a kidney bean. Visitors flock to take funhouse mirror-like photos of their reflections in its smooth surface.

The park also features the Crown Fountain’s two 50-foot glass block towers, the tranquil Lurie Garden, the Pritzker Pavilion for free concerts, and the seasonal ice skating rink. Millennium Park is a gorgeous (and free!) place to stroll, take photos and enjoy Chicago’s city vibrancy.

4. Take in Stunning Views from Willis Tower Skydeck

For unmatched views, head up to Willis Tower Skydeck on the 103rd floor. This observation deck provides unparalleled panoramic views of Chicago from 1,353 feet up.

On a clear day you can see up to 50 miles away! Peer straight down to the streets below from The Ledge‘s glass boxes extending 4.3 feet out from the building – it will take your breath away.

Look for famous Chicago buildings like the John Hancock Center, the Wrigley Building clock tower and the neo-gothic Chicago Tribune building. Gaze over huge Lake Michigan stretching to the horizon. You can even see four different states. A visit to Skydeck is easily one of the top things to do in Chicago.

5. Explore The Field Museum and its Dinosaur Fossils

The Field Museum houses over 40 million artifacts and specimens making it one of the largest natural history museums in the world. The most iconic exhibits feature their outstanding collection of dinosaur and other ancient fossils.

Don’t miss seeing “SUE” – the largest and best-preserved Tyrannosaurus rex fossil ever found! SUE is a staggering 67 million years old.

Other highlights include Egyptian mummies and sarcophagi, the Hall of Gems showcasing giant gemstones, and famous taxidermy dioramas depicting wildlife around the world. Give yourself several hours to explore this Chicago gem.

6. See a Show at The Second City Comedy Theater

Get ready to laugh out loud at Chicago’s legendary Second City improv comedy theatre. This innovative comedy troupe has nurtured the talents of Chris Farley, Tina Fey, Stephen Colbert, Steve Carell and many other funny stars.

Catch a hilarious improv or sketch comedy show at this intimate theater. The casts change frequently so you’ll get something fresh even if you’ve visited before. The lively atmosphere and talented performances make for an entertaining night out.

7. Marvel at Sharks at the Shedd Aquarium

Get eye-to-eye with over 32,000 aquatic animals at Chicago’s Shedd Aquarium. Home to sharks, dolphins, stingrays and other fascinating creatures, it’s one of the oldest public aquariums in the world.

Don’t miss the Wild Reef exhibit where you can walk through floor-to-ceiling windows surrounded by sharks, sea turtles and giant fish. The realistic rock reef and shipwreck artifacts make you feel immersed underwater.

Make sure to catch one of the informative Aquatic Show featuring Shedd’s beluga whales, dolphins and penguins. You’ll learn about marine life behaviors and may even see the dolphins leaping.

8. Take in Art at the Art Institute of Chicago

With its expansive collections, the Art Institute of Chicago houses one of the oldest and largest art museums in the United States. Their diverse permanent collection has over 300,000 works spanning thousands of years.

See iconic paintings like Edward Hopper’s Nighthawks, Grant Wood’s American Gothic, and Georges Seurat’s pointillism masterpiece A Sunday on La Grande Jatte.

Other highlights include an incredible Impressionist and Post-Impressionist collection, armor exhibitions, decades of modern art, and the Thorne Miniature Rooms showcasing tiny displays of historic interiors.

You could spend all day wandering the various galleries and time periods. Don’t miss it on your Chicago trip!

9. Ride to the Top of the Hancock Building

For amazing views, head to the John Hancock Center’s 94th-floor observatory. Floor-to-ceiling windows provide sweeping 360-degree views spanning up to 80 miles.

Gaze down on Chicago neighborhoods, parks and beaches. Spot the Willis Tower and other city icons. Look all the way across the expanse of Lake Michigan to Indiana dunes on a clear day. At night, city lights spread out around you in a sparkling sea.

Choose from food and drink or fine dining at their Lavish restaurant 1,000 feet up. Sunset is a beautiful time to visit. Definitely one of the top Chicago attractions for views.

10. Relax at Millennium and Maggie Daley Parks

When you need a breather from Chicago’s hustle and bustle, relax at Millennium Park and the adjoining Maggie Daley Park. Together these two downtown parks give both locals and tourists room to unwind.

Millennium Park features the iconic Cloud Gate “Bean” sculpture, tranquil gardens, outdoor concert pavilions, and the winter ice rink.

Maggie Daley Park includes playgrounds, rock climbing walls, mini golf, roller skating ribbons, and more. In winter, its ice skating trail transforms into an awesome quarter mile long skating path.

You could easily spend a whole afternoon enjoying the parks’ scenery and activities.

11. Take in a Chicago Cubs Baseball Game at Wrigley Field

Experience America’s favorite pastime by taking in a Chicago Cubs baseball game at historic, iconic Wrigley Field. Opened in 1914, it’s one of baseball’s oldest and most storied ballparks.

Watch for fly balls hit onto Waveland or Sheffield Avenues. Yell for the Cubbies along with locals. Eat Chicago-style hot dogs and peanuts in the stands. And don’t leave before you check out the statue of beloved Cubs broadcaster Harry Caray leading fans in song.

With old-timey traditions and diehard fans, it’s a classic way to enjoy Chicago’s infectious local spirit.

12. Visit the Chicago Cultural Center

The Chicago Cultural Center offers free arts programming and exhibits in a gorgeous historic building. Originally the city’s central public library, it features the world’s largest Tiffany stained glass dome and two 38-foot Tiffany glass mosaics.

See ongoing art exhibits, attend free concerts, take a building tour, or just relax in the lounge areas. The Cultural Center also hosts many Chicago events like art fairs, flower shows and markets. Don’t miss this impressive historic spot.

13. Take in Stunning Views from 360 Chicago

Head to 360 Chicago’s 94th-floor observatory for amazing panoramic city views. Their open-air Skywalk offers unique unobstructed views and photo ops.

In addition, their TILT experience uses floor-to-ceiling windows to tilt visitors out 30 degrees over Michigan Avenue. This thrilling way to look straight down is not for the faint of heart!

360 Chicago, formerly the John Hancock Observatory, requires advance timed-entry tickets. It’s centrally located making it easy to visit. Day or night, their observatory offers some of the best views in Chicago.

14. Tour Historic Robie House by Frank Lloyd Wright

Tour the Robie House, one of Frank Lloyd Wright’s most famous and influential Prairie-style homes. The house design was revolutionary for its time and launched Wright’s career as America’s greatest architect.

See Wright’s open floor plan, low rooflines, and strong horizontal lines that mimic the flat prairie landscape. Exhibits provide insight into Wright’s personal life and architectural talents.

Guided tour tickets for the interior should be booked as far in advance as possible. Or you can walk around the exterior for free. This National Historic Landmark is an architecture must-see.

15. See the Chicago Skyline from Lake Michigan

Get out on the water to see Chicago’s towering skyline from a unique vantage point. Options include boat tours, kayaking, paddleboarding, or water taxis.

Popular places to launch are at Navy Pier, the Chicago Riverwalk, and North Avenue Beach. As you look back towards the city, the skyline takes on a whole new grandeur rising above Lake Michigan’s blue horizon.

It’s also fun to watch planes descending low towards O’Hare Airport flying right past downtown. Don’t forget your camera!

16. Catch a Show at The Green Mill Jazz Club

Experience Chicago’s famous jazz scene at the historic Green Mill Jazz Club. Opened in 1907, the club hosted jazz legends like Louis Armstrong, Count Basie, Billie Holiday and more. Al Capone even frequented it during Prohibition.

Sip a cocktail and listen to jazz bands in this intimate, retro parlor setting. On Sundays the club features nationally-known jazz groups. Poetry slams on Tuesdays and swing dancing on other nights liven up the scene.

Make reservations on weekends when there’s a small cover charge. The talented performers and historic ambiance make Green Mill a quintessential Chicago nightlife stop.

17. Visit Lincoln Park Zoo

Lincoln Park Zoo offers free admission to see lions, snow monkeys, penguins, and more up close. It’s an especially good budget-friendly option for families and one of the few major Chicago attractions that is free.

Don’t miss the large Regenstein African Journey exhibit where you can safely view gorillas, rhinos, zebras and other African animals in naturalistic habitats. See polar bears diving at the glass-walled pool. And check out baboons, a pygmy hippo, and warthogs at the Kovler Lion House.

With over 1,200 animals, this 35-acre zoo lets you easily spend half a day. And you can’t beat the price!

18. Explore The 606 Elevated Urban Trail

The 606 (named for Chicago’s ZIP code prefix) is an innovative 2.7 mile long elevated trail on former railway tracks. Walk, jog, bike, or skate along the trail through 4 Chicago neighborhoods – Bucktown, Wicker Park, Humboldt Park, and Logan Square.

Artwork installations, event programming, native plantings, seating areas, and even fitness equipment make The 606 more than just a way to get around. It attracts over 100,000 visitors a month!

Exploring neighborhoods from this vantage point gives you a unique peek into Chicago’s culture. The 606 is also a prime way to experience green space in the city.

19. See the Chicago Theater Marquees and Take In a Show

Chicago’s Theater District clustered around State and Randolph Streets is nicknamed the Great White Way for its neon-lit theater marquees.

Broadway smash hits like Hamilton, Wicked, and Moulin Rouge play long engagements here. Catch them at venues like CIBC Theatre or the Cadillac Palace Theatre.

Smaller theaters like Steppenwolf, Goodman, and Second City feature edgy dramas, comedies, and experimental works. And the historic Chicago Theatre with its iconic sign hosts concerts and performances.

With so many options, Chicago’s theater scene has something for all interests. It’s one of the top nightlife experiences in the city.

20. Explore Navy Pier for Rides, Food, and Views

Last but certainly not least, Navy Pier offers plenty of family fun. The pier juts a 1/2 mile out into Lake Michigan from Chicago’s shoreline.

Must-see attractions include riding the 196-foot high Centennial Wheel for spectacular views. Play midway rides and carnival games. Grab a bite from the international food court.

Catch a show at the classic IMAX theater or Shakespeare theater docked on the pier. In summer, watch fireworks shows on Wednesdays and Saturdays. With so many options, you can easily spend a whole day exploring Navy Pier.


From stunning architecture to world-class museums, Chicago offers endless things to see and do. Iconic attractions like Willis Tower, Millenium Park’s “Bean”, and Wrigley Field combine with arts, culture, entertainment, and dining for a fantastic visitor experience.

Use this list to plan an unforgettable trip that takes advantage of Chicago’s immense city vibrancy and spirit. You’re guaranteed to go home with great memories!

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