The Top 15 Attractions in Chicago

Regardless of the vacation atmosphere you seek, the Windy City has something to offer everyone.

From bustling hotspots like the Art Institute of Chicago and the Picasso sculpture to the laid-back charm of neighborhoods like Andersonville on the North Side, Chicago will quickly start to feel like home.

If possible, dedicate about three days to your Chicago visit, allowing you to enjoy a range of activities at a leisurely pace. The city caters to all budgets, offering everything from high-end dining to numerous free attractions such as lovely parks and musical performances at The Grant Park Music Festival.

With so much to see and do, where should you begin? Take advice from the locals and navigate the city via bus or L train, just like they do. Here are 15 fantastic ways to experience Chicago as the locals do. Follow our Chicago travel tips for the best experiences, and soon you'll be exploring the Windy City like an expert.

1. Enjoy a Day at the Ballpark

With both the Chicago Cubs, who play at the historic Wrigley Field, and the Chicago White Sox, based at Guaranteed Rate Field, catching a baseball game is essential.

Throughout the year, fans can also enjoy a wide range of sporting events featuring top-notch athletes. Football enthusiasts can cheer for the Chicago Bears, while basketball fans have the Chicago Bulls and the women's Chicago Sky to support. Don’t overlook the Chicago Blackhawks in hockey, as well as the Chicago Fire FC men’s soccer team and the Chicago Red Stars women’s soccer team. It’s safe to say that Chicago is a sports-loving city.

On any given day, you’ll find fans flocking to arenas, stadiums, and bars to cheer for their favorite teams. Tickets for popular games tend to sell out fast, and hotel rates can soar, particularly during peak tourism seasons, so it’s wise to plan in advance.

2. Experience an Architecture River Cruise

A cruise along the Chicago River to take in the stunning skyline and learn about this important urban waterway is a must-do among Chicago attractions. Various cruises are available, with a highly regarded option provided by the Chicago Architecture Foundation. Even if you’re not an architecture enthusiast, the tales behind the city’s iconic buildings and their creators will captivate you. The boat tours now operate during both the day and sunset, featuring indoor and outdoor seating.

3. Explore Chicago’s Cocktail Culture 

The Violet Hour is often credited as the birthplace of craft cocktails in Chicago, making it essential to stop by one of the city's original speakeasies. When the yellow light is on, the doors are open. You’ll step through velvet curtains into a sophisticated cocktail bar reminiscent of a bygone era. 

Make sure to keep your phone on silent and dress to impress, as if you’re meeting the parents, to ensure you gain entry. 

However, the pinnacle of cocktail experiences in Chicago might just be at Aviary, known for its intricate molecular drinks that can be enjoyed on their own or paired with artfully presented small plates. This venue is part of the renowned Michelin-starred Alinea Group, which also includes the speakeasy The Office located below it. 

For those who can't get enough of Chicago’s speakeasy scene, make sure to check out The Drifter and Lady Bird. The Drifter is tucked away on the lower level of River North’s historic Green Door Tavern, the oldest bar in the city. You’ll find the entrance behind a bookshelf on the way to the restroom. Plus, enjoy live Vaudeville performances every hour (cover charge applies). 

Lady Bird, located in the basement of the Hoxton in the West Loop, boasts a cozy atmosphere with live music ranging from jazz to rock every Thursday through Saturday, evoking a 1960s glam vibe. 

4. Discover the Magic of Chicago 

Chicago is home to some of the most renowned magicians in the industry, making it a vibrant center for an emerging magic scene. 

In the Loop, you can dress to impress for an enchanting evening of magic with Dennis Watkins, a third-generation magician, at the luxurious Palmer House Hilton. Cocktail attire is encouraged, so come well-dressed.

For a more relaxed vibe, head north to the Chicago Magic Lounge. True to its magical theme, the entrance looks like a laundromat. Once inside, you’ll find a host ready to lead you to a show or the bar, where bartenders perform close-up magic while serving delightful drinks. If you’re visiting Chicago with kids, the Magic Lounge offers a family matinee show every other Sunday, welcoming all ages five and up—an ideal winter outing for families!

5. Enjoy the blues and rock scene

Few musical styles are as intrinsically linked to Chicago as the blues—specifically, the electric blues. When Muddy Waters and his peers plugged in during the 1950s, their guitar riffs soared to new heights, giving rise to the vibrant Chicago blues scene.

Experience authentic blues in local venues like Buddy Guy's Legends, where the legend himself occasionally performs, or at Rosa's Lounge, which has a grittier atmosphere. The Chicago Blues Festival, held in Millennium Park each June, showcases top-notch talent.

Planning tip: The blues set the stage for rock and roll, and you’ll find charming venues featuring indie bands on many street corners. Start your search at places like Thalia Hall, Hideout, and Reggies.

6. Explore local shops in Chicago's trendy neighborhoods

Chicago is a lively mix of neighborhoods. To truly immerse yourself in the city like a local, venture beyond the Loop, skip Michigan Avenue, and support local shops that showcase the city’s rich diversity. 

Andersonville, located on the North Side, boasts fascinating Swedish heritage. The Clark Street stretch between Foster and Bryn Mawr is filled with nostalgic boutiques that exude Wes Anderson charm, while Wicker Park and Bucktown cater to local hipsters and young families.

Heading south to Little Village reveals a vibrant Mexican community, making it the city’s second-highest shopping district. Visit Comercio Popular to shop from unique artisans and enjoy events inspired by Mexico. 

Conclude your shopping journey in Hyde Park, home to Michelle and Barack Obama (when they’re in Chicago). The Silver Room is a must-visit – this Black-owned store showcases a variety of products highlighting Black culture and artisans.

Planning tip: Michigan Avenue is more touristy and caters to big brands oriented, but it's worth a stop between Thanksgiving and Christmas for seasonal decorations and festive storefronts.

7. Savor dishes at award-winning eateries 

Throughout the years, Chicago has built a strong reputation as a food haven, thanks to talented chefs like Grant Achatz, Rick Bayless, Stephanie Izard, Erick Williams, Bill Kim, and Carlos Gaytan. 

For upscale dining, make your way to the West Loop and choose from a selection of top culinary masters, James Beard award winners, and Michelin-starred chefs. 

Joe Flamm’s Rosemary, an Italian-Croatian eatery, is among the city's hottest spots, while Gibson’s Italia specializes in exquisite Florentine steaks for the power dining crowd, and The Publican offers an exceptional brunch. Must-try classics include The Girl & The Goat and Frontera Grill. Don’t miss Virtue in Hyde Park for award-winning new Southern cuisine, a favorite of the Obamas. 

For a splurge, secure a reservation at Grant Achatz’s restaurant Next, where the concept, decor, and menu transform entirely several times a year.

If you're exploring Chicago on a budget, make your way to the Athenian Room in Lincoln Park for their chicken kalamata (a Tina Fey favorite). Lou Malnati’s Pizza is famous for its deep-dish pies. Check out Oasis in the Loop for Lebanese dishes or Aguascalientes in Little Village for delicious Mexican cuisine.  

8. Experience the Wonders of Millennium Park

Nestled in the lively core of Chicago, Millennium Park dazzles with playful public art. Don't miss your chance to walk beneath Anish Kapoor's Cloud Gate, affectionately known as 'the Bean,' and feel its sleek, reflective surface. Cool off in the summer as you let the whimsical human gargoyles of Jaume Plensa’s Crown Fountain drench you, or spread a blanket at Pritzker Pavilion, the stunning Frank Gehry-designed silver band shell, as twilight descends and beautiful live music fills the air. 

Planning tip: Be sure to check the schedule for free summer concerts running from June to August in Millennium Park – enjoy jazz and world music on Mondays and Thursdays, and classical music on Wednesdays, Fridays, and Saturdays.

9. Embark on a Windy City Tour  

Curious about Chicago's hidden gems? Join a guided tour to unveil intriguing facts and insider knowledge that could give you an edge at Trivia Night back home. 

To dive deeper into Chicago's neighborhoods, consider booking a tour with TikTok historian Shermann “Dilla” Thomas. He offers engaging walks through Bridgeport/Stockyard, Bronzeville, or Pullman/Roseland with his company, Chicago Mahogany Tours.

10. Enjoy a night of laughter at local comedy shows 

Improv comedy was born in a Chicago bar fifty years ago when a group of comedians began performing intentionally unstructured skits. Second City remains a powerhouse for top talent, while numerous other improv theaters thrive on audience suggestions fueled by drinks. 

Chicago boasts over 200 theaters, featuring powerhouse companies like the star-studded Steppenwolf, the Black Ensemble Theater, and many edgy, thought-provoking 'off-Loop' troupes, including The Neo-Futurists.

Getting around Chicago

11. Take a leisurely walk along Navy Pier

Extending from the skyline into the sparkling waters of Lake Michigan, the half-mile-long Navy Pier is a must-see destination in Chicago. Its allure lies in the refreshing breezes and stunning vistas, especially from the thrilling, 196ft (59.7m) Ferris wheel. Exciting rides, splash fountains, grand boats, and delicious treats delight visitors of all ages. 

Live music, Shakespearean performances, and spectacular fireworks shows entertain everyone else. Recent renovations have introduced public plazas, performance spaces, art installations, and a variety of free cultural programs.

12. Uncover African American History at the DuSable Museum 

The DuSable Museum is the oldest independent African American museum in the U.S., narrating the narrative of the Black American experience through significant figures and events. 

Current exhibits honor Chicago’s first Black mayor, Harold Washington, display art gathered by the publisher of Ebony and Jet magazines, and present scenes from the civil rights movement. As a nonprofit, admission is free, though donations are welcomed. 

 13. Journey through the ocean and the cosmos 

One of Chicago's greatest features is that many top attractions are conveniently clustered around Lake Michigan. 

Your little explorers can dive into the sea and the cosmos with two exhilarating lakefront attractions. Visit the John G. Shedd Aquarium, home to vast tanks brimming with angel fish, octopuses, beluga whales, and sharks. For aspiring astronomers, the Adler Planetarium offers a chance to launch rockets and gaze into the universe through a giant telescope.

14. Immerse yourself in culture at the Art Institute

The Art Institute of Chicago is a cherished destination for locals and a must-see for visitors. Even a brief visit will leave a lasting impression. 

The museum boasts iconic works, including modernist masterpieces by Mondrian and Georgia O’Keeffe, alongside enchanting impressionist paintings by Monet and Matisse. On warm days, unwind at the garden café before exploring the new gallery showcasing ancient Egyptian masks and sculptures. Don’t forget to take a souvenir photo with one of the majestic lions at the entrance. 

15. Relish the outdoors at Grant Park 

Chicago offers a wealth of inexpensive and free attractions, making it an enjoyable destination even on a tight budget. 

Stroll through Grant Park, where you’ll find lovely gardens, cozy benches for relaxation, and beautiful lake views. Take the kids to Maggie Daley Park to burn off energy climbing, zooming down tube slides, or crossing a suspension bridge. Older kids can tackle the climbing wall or rent rollerblades. If you’re in town during winter (November-February), be sure to register for tickets to the Ice Skating Ribbon. 

As night approaches, head to Buckingham Fountain, a breathtaking 1927 landmark that features dazzling water displays illuminated by colorful lights until 11pm. Just remember to pack some mosquito repellent. 

Continue planning your Chicago adventure:

Discover the best times to visit Chicago.

Navigating Chicago is simpler than you might expect – here’s how.

Discover the top free activities in Chicago – and ways to explore on a budget.

Uncover national parks, wineries, and more with these Chicago day trips.