Chicago, also known as The Windy City, is one of the most vibrant travel destinations in the United States. Whether you’re visiting for a weekend getaway, a family trip, or a solo adventure, Chicago offers an unmatched blend of world-class architecture, iconic attractions, cultural institutions, and mouthwatering food.
If you’re searching for the best things to do in Chicago, this guide will help you plan the perfect itinerary for the remainder of 2025 and 2026.
1. Millennium Park & The Bean
No Chicago trip is complete without a photo at Cloud Gate (aka The Bean) in Millennium Park. This free attraction is a hub for art, music, and seasonal events.
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Best for: First-time visitors & Instagram photos
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Tip: Visit early in the morning for fewer crowds.
2. Navy Pier
One of Chicago’s most famous landmarks, Navy Pier offers restaurants, theaters, boat cruises, and the Centennial Wheel with sweeping lakefront views.
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Best for: Families & couples
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Don’t miss: Fireworks shows in summer.
3. Willis Tower Skydeck
Step out onto The Ledge, a glass balcony extending 4 feet outside the 103rd floor. The Willis Tower Skydeck provides jaw-dropping city views.
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Best for: Thrill seekers & photographers
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Tip: Sunset visits give the best photos.
4. Art Institute of Chicago
Home to Grant Wood’s American Gothic and Monet’s water lilies, this museum is a must-see for art lovers.
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Best for: Culture seekers
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Plan for: At least 2–3 hours.
5. Chicago Riverwalk
Take a stroll along the Chicago Riverwalk, lined with cafes, public art, and boat tour docks. Architecture cruises are highly recommended.
6. Chicago Architecture Boat Tour
Chicago is the birthplace of the skyscraper. A river architecture cruise showcases iconic buildings like the Tribune Tower and Marina City.
7. Magnificent Mile
If shopping is on your list of things to do in Chicago, the Magnificent Mile delivers luxury retailers, historic landmarks, and plenty of dining options.
8. Lincoln Park Zoo (Free)
One of the oldest zoos in the U.S., Lincoln Park Zoo is free year-round and perfect for families.
9. Shedd Aquarium
See beluga whales, sea otters, and colorful reef fish at the Shedd Aquarium, one of the world’s largest indoor aquariums.
10. Field Museum
From Sue the T. Rex to ancient Egyptian mummies, the Field Museum is a bucket-list attraction.
11. Adler Planetarium
Perfect for stargazers, the Adler Planetarium is America’s first planetarium and features immersive sky shows.
12. Museum of Science and Industry
From a real WWII submarine to interactive science exhibits, this museum fascinates all ages.
13. Chicago Food Tour
Chicago is world-famous for deep-dish pizza, Italian beef sandwiches, and Chicago-style hot dogs. Food tours let you taste it all.
14. Wrigley Field
Catch a Chicago Cubs game at historic Wrigley Field, one of the most iconic baseball stadiums in America.
15. United Center
Sports fans can also watch the Chicago Bulls (NBA) or Chicago Blackhawks (NHL) at the United Center.
16. Lakefront Trail
Walk, run, or bike the 18-mile Lakefront Trail, offering breathtaking views of Lake Michigan and Chicago’s skyline.
17. 360 Chicago Observation Deck
Located in the John Hancock Center, 360 Chicago offers panoramic views and the thrilling TILT experience.
18. Chicago Theatre
Snap a photo of the iconic Chicago Theatre marquee or catch a live performance.
19. Garfield Park Conservatory
A lush, tropical escape with free admission, the Garfield Park Conservatory is one of the largest in the U.S.
20. Chicago Cultural Center (Free)
Home to the world’s largest Tiffany glass dome, this free cultural hub hosts rotating art exhibits and concerts.
21. Andersonville & Wicker Park
For a local experience, explore neighborhoods like Andersonville (Swedish heritage, indie shops) or Wicker Park (trendy dining, nightlife).
22. Chicago Festivals
Chicago is a city of festivals:
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Taste of Chicago (food)
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Chicago Blues Festival (music)
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Lollapalooza (global music festival)
23. Kayaking on the Chicago River
For adventure seekers, kayaking along the Chicago River is an unforgettable way to see the skyline.
24. Chicago History Museum
Learn about the Great Chicago Fire and the city’s vibrant past at the Chicago History Museum.
25. Winter in Chicago
If visiting in winter, try ice skating at Millennium Park, Christmas markets, and indoor museum hopping.
Insider Travel Tips
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Best Time to Visit: May–September for festivals and outdoor activities.
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Budget Tip: Many museums offer free days for Illinois residents — check calendars before visiting.
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Transportation: Use the CTA (“L” train) for affordable city travel.
Final Thoughts
From iconic attractions like The Bean and Navy Pier to hidden gems like Garfield Park Conservatory, Chicago offers endless ways to explore. Whether you’re here for art, sports, food, or skyline views, you’ll never run out of things to do in Chicago.
