Top 25 Things to Do in Chicago on Your First Visit

Visiting Chicago for the first time? You’re in for an unforgettable trip. Chicago, Illinois, offers a perfect mix of history, culture, food, and breathtaking lakefront views. On my first visit, I wanted to see the must-do in Chicago attractions and also find some hidden gems. From world-famous museums to cool rooftop cafés, here’s a detailed guide with everything you need to know, including prices, official websites, and the best local recommendations. If you’re searching for things to do in Chicago or even free things to do in Chicago, this guide has you covered.

1. Millennium Park & The Bean (Cloud Gate)

No trip to Chicago is complete without visiting Millennium Park. The star attraction is Cloud Gate, also known as “The Bean,” one of the most Chicago must see spots. It’s free to enter, and you can enjoy live music, art installations, and the beautiful gardens nearby. I went early in the morning to avoid the big crowds, and it was worth it!

Price: Free

Address: 201 E Randolph St, Chicago, IL

2. Willis Tower Skydeck

For one of the top things to do in Chicago, head to the Willis Tower Skydeck. Standing 1,353 feet above the city, the glass ledge lets you step out and look straight down. It’s an incredible experience if you’re not afraid of heights!

Price: Adults $32+, Children $24+

Address: 233 S Wacker Dr, Chicago, IL

3. Navy Pier

The Navy Pier is one of the best Chicago attractions for families. With a giant Ferris wheel, boat tours, restaurants, and seasonal events, it’s always lively. I especially enjoyed watching the fireworks during summer nights.

Price: Free entry, rides/attractions vary $10–$30

Address: 600 E Grand Ave, Chicago, IL

4. Art Institute of Chicago

If you’re into art, the Art Institute of Chicago is a must. It’s one of the oldest and largest art museums in the U.S. and home to works by Van Gogh, Monet, and Picasso. I spent hours here and still couldn’t see everything!

Price: Adults $32, Students/Seniors $26, Children under 14 free

Address: 111 S Michigan Ave, Chicago, IL

5. Chicago Riverwalk

Walking along the Chicago Riverwalk is one of the coolest free activities in the city. You’ll find cafés, bars, and art displays along the river. Try renting a kayak or just sit with a coffee and watch the boats pass by.

Price: Free (extra for kayaking/food)

Address: Along the Chicago River, Downtown

6. 360 Chicago Observation Deck (John Hancock Center)

Another amazing view comes from the 360 Chicago Observation Deck. The unique feature here is “Tilt,” a moving glass platform that tilts you over Michigan Avenue. It gave me chills but the view was worth it.

Price: Adults $30, Children $20, Tilt +$9

Address: 875 N Michigan Ave, Chicago, IL

7. Shedd Aquarium

The Shedd Aquarium is one of the best things to do in Chicago with family. From beluga whales to penguins, the marine life here is incredible. I recommend booking tickets online because it gets crowded, especially on weekends.

Price: Adults $39.95, Children $29.95

Address: 1200 S Lake Shore Dr, Chicago, IL

8. Field Museum of Natural History

If you’re into history, the Field Museum is a must. Home to “Sue,” the most complete T. rex ever discovered, this museum is fascinating for both adults and kids.

Price: Adults $32, Children $23

Address: 1400 S Lake Shore Dr, Chicago, IL

9. Adler Planetarium

The Adler Planetarium is perfect for astronomy lovers. With interactive exhibits and amazing sky shows, it’s a cool spot to learn and relax. The location also offers some of the best skyline views of Chicago.

Price: Adults $19+, Children $8+

Address: 1300 S Lake Shore Dr, Chicago, IL

10. Chicago Architecture River Cruise

The Chicago Architecture River Cruise is one of the most popular must see in Chicago activities. Learning about the city’s skyline while cruising down the river is both relaxing and educational. I loved it as it gave me a different perspective of the city.

Price: $40–$50 per person

Departure: Multiple docks along the river

11. Lincoln Park Zoo

The Lincoln Park Zoo is one of the best free things to do in Chicago. Open every day of the year, it’s perfect for families or anyone who enjoys wildlife. I was surprised by how big it is considering it’s free.

Price: Free

Address: 2001 N Clark St, Chicago, IL

12. Chicago Theatre Tour

The historic Chicago Theatre is an iconic landmark. Taking the backstage tour was a highlight of my trip—I got to see behind the scenes of this legendary performance space.

Price: Around $20 per tour

Address: 175 N State St, Chicago, IL

That’s just the beginning! In the second part, I’ll continue with more stuff to do in Chicago including music venues, best restaurants, rooftop cafés, hotels, beaches, family-friendly activities, and seasonal events like things to do in Chicago in December. Keep reading!