Ultimate guide to 16 fun things to do in Chicago

It might be known as the Windy City for a different reason, but there are so many fun things to do in Chicago that’ll blow you away. From ballroom dancing and helicopter rides to tasting tours of local fare, Chicago is filled with exciting things to add to your adventure.

Architecture cruises across Lake Michigan and observation decks with 360-degree views are great options if exploring Chicago’s cityscape is on your list. If you prefer dessert to design, this city has great food experiences too — tasting tour in the foodie neighborhood of Lincoln Park, anyone?

Make your own fun-filled itinerary with these 16 unique experiences in Chicago.

Fun things to do in Chicago as a couple

1. Go for a romantic cruise on Lake Michigan

Relaxing on a boat with your partner while sailing across Lake Michigan is one of the top things to do in Chicago for couples. Pass some of Chicago’s most iconic sights, like the Willis Tower and Grant Park, while floating along the city skyline. You’ll see why it's so easy to fall for Chicago after seeing its beauty from the water.

Best time to go:

Sail at sunset for the ultimate date night or special occasion under the setting sun.

Address and opening hours:

Meeting point locations and start and end times will depend on the cruise you book.

2. Dance the night away with a dance class

For couples wanting to try something new and be active, why not learn to salsa or swing together during a dance class in Chicago? Neighborhoods like Bronzeville and Pilsen have deep connections to music and dance, from jazz to flamenco, so joining a class to learn these styles is an immersive way to experience Chicago’s dance history.

Insider tip:

Ballroom Dance Chicago is a popular spot for both private and group dance lessons.

3. Get a bird's-eye view on a helicopter tour

Nothing says luxury quite like a helicopter ride over Chicago's best landmarks. Along with unrivaled perspectives of Chicago from the clouds, pilots will also often fill you in on interesting facts about the city's history during the flight. A helicopter tour is one of the most unique things to do on any Chicago vacation.

Insider tip:

Go after dark for romantic illuminated city views, and don't forget to prepare a bottle of champagne.

4. Enjoy views from the 360 Chicago Observation Deck

If you've already done the helicopter flight, traveling to the 94th floor of the former John Hancock Center to the 360 Chicago Observation Deck may be the next best thing. The observation deck is the highest point in the city for panoramic views of Lake Michigan and even neighboring states. Treat your partner to the high life while enjoying drinks in Chicago's highest bar.

Highlight:

Don’t miss the Tilt ride, windows that let you tilt out from the building.

Address and opening hours:

875 N Michigan Ave 94th floor, Chicago, IL 60611. Open 9:00 AM-11:00 PM every day.

Fun things to do in Chicago with kids

5. Meet dinosaurs at the Field Museum of Natural History

As you walk through the doors of Chicago’s renowned Field Museum, you're faced with a huge replica skeleton of a titanosaur that kids can touch. The famous T. rex Sue also waits to amaze curious minds. All ages will have fun exploring the dinosaur models, fossils, and mummies.

Highlight:

Don't miss the Family PlayLab, where your kids can play scientists and excavate bones.

Address and opening hours:

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

6. Have fun in the Play Garden

Set the kids loose at the Play Garden in Maggie Daley Park. This 20-acre public park has a winding path with interactive play spaces, making it one of the top things to do with kids in Chicago. Little ones will have lots to do and see, and there are plenty of picnic spaces and seating for adults to relax.

Highlight:

The water play areas are a perfect way to cool off during summer in Chicago.

Address and opening hours:

337 E Randolph St, Chicago, IL 60601. Open 6:00 AM-9:00 PM every day.

7. Take a selfie with The Bean

When it comes to things to see in Chicago, you can expect to see The Bean in almost every Chicago travel guide. This bean-shaped reflective sculpture, actually named Cloud Gate, is a sculpture by Anish Kapoor that marks the entrance to Millennium Park and is one of the most recognizable public artworks in the city. Taking a photo by The Bean is an essential Chicago experience.

Highlight:

Look out for Jaume Plensa's interactive video sculpture, the Crown Fountain, right next to Cloud Gate.

Address and opening hours:

201 E Randolph St, Chicago, IL 60602. Open 6:00 AM-11:00 PM every day.

8. Get creative at LEGOLAND Discovery Center

Exploring the LEGOLAND Discovery Center offers LEGO rides and fun activities for kids to try out and explore, including a 4D Cinema and millions of LEGO Bricks. Creativity and imagination take center stage, allowing children and adults to build and interact with the colorful world of LEGOs.

Highlight:

Special events, themed nights, and workshop sessions with Master Model Builders add to the fun.

Address and opening hours:

601 N Martingale Rd, Schaumburg, IL 60173. Open Monday-Friday, 10:00 AM-5:00 PM; and Saturday and Sunday, 10:00 AM-7:00 PM.

Fun things to do in Chicago on your own

9. Spend an afternoon at Navy Pier

Looking for a scenic place to spend an afternoon on your own? A trip to Chicago's beautiful lakefront destination, Navy Pier, should do the trick. It was conceived as a freight dock and has since evolved into a must-see fun destination and one of Chicago’s top attractions for its unbeatable views of the glistening Lake Michigan.

Highlight:

Ride on the Centennial Wheel and look at the city from 200 feet in the air.

Address and opening hours:

600 E Grand Ave, Chicago, IL 60611. Open Sunday-Thursday, 11:00 AM-9:00 PM; and Friday-Saturday, 11:00 AM-10:00 PM.

10. Take an architecture river cruise

Chicago is known for its unique architecture, as seen through its many historic and complex buildings. If you’ve already driven or walked around the city and think you’re familiar with Chicago’s architecture, hop on an architecture cruise, and you’ll be surprised to find things you didn’t notice before. See why many believe there's no better vantage point to admire the city's architecture than from the Chicago River and Lake Michigan.

Highlight:

Look for the Tribune Tower, known for its neo-Gothic design, and the Wrigley Building, a standout example of Spanish Colonial Revival architecture.

11. Find tranquility at Garfield Park

Take a trip to the Garfield Park Conservatory and bask in the peace of 12 acres of greenery. Thousands of plants and unique exhibits create a serene escape from the city, allowing visitors to connect with nature in a beautifully curated environment. Find towering tropical plants in the Palm House and feel like you’re in a bygone era in the dense Fern Room. The conservatory also hosts workshops and seasonal displays.

Highlight:

Swing by the Horticulture Hall on weekends for a lavender oat milk cold brew.

Address and opening hours:

300 N Central Park Ave, Chicago, IL 60624. Open Wednesday-Sunday, 10:00 AM-5:00 PM.

12. Scream your lungs out at a wrestling show

Get a front-row seat to hard-hitting action in Chicago and cheer on your favorites in the wrestling ring. Experience AAW, Warrior Wrestling, and Freelance Wrestling with established and up-and-coming talent alongside international stars. Whether you're watching lucha libre in the park or a professional match, live wrestling is a unique way to engage with Chicago's longstanding wrestling culture.

Highlight:

Attend the annual Windy City Classic for top-tier wrestling and a high-energy atmosphere.

13. Learn the true stories of Chicago's mob past

Chicago's mob history is rich with tales of notorious gangsters and events that shaped the city's underworld. Those wanting to explore this part of the city's past should head to neighborhoods like Little Italy and the South Side, which were significant centers of mob activity during the Prohibition era. Al Capone, one of the most infamous mobsters, ran his operations from the Lexington Hotel, which became a hub of criminal enterprise. Another key site is the Green Mill Cocktail Lounge in Uptown, a former speakeasy where gangsters would gather.

Insider tip:

For a deep dive into the mob's history and the most significant spots in Chicago, join a mob-themed tour with an expert guide.

Fun things to do in Chicago for food and drinks

14. Satisfy your palate on a food tour

Figuring out what to eat in Chicago is made easy with a food tour. With a food guide by your side, wander through neighborhoods like the West Loop, known for its trendy restaurants and upscale eateries, or Pilsen, where Mexican flavors dominate the scene, and taste as you go. Get led straight to Chicago's hidden gems and most iconic eateries for a true taste of the city.

Highlight:

Don’t miss trying Chicago’s iconic deep-dish pizza, a classic Chicago-style hotdog, and a slice of rich, cheesy Italian beef sandwich.

15. Take a brunch cruise with a side of views

Joining a brunch cruise in Chicago is a fun way to combine sightseeing with a meal. As you sail, you can take in beautiful daytime views of the city skyline, including landmarks like the Chicago Harbor Lighthouse, Wrigley Building, Marina City, and Aqua Tower. The bonus is you can enjoy brunch and drinks with a moving panorama from the movies.

Insider tip:

If you aren't a morning person, there are lunch and dinner cruises too.

16. Sip on Chicago's best brews

Chicago’s brewing history dates back to the 19th century, with the city playing a pivotal role in the Midwest beer scene. Sampling Chicago brews is the best way to experience the city's innovative craft beer movement. Areas like the West Loop and Wicker Park are home to renowned breweries such as Revolution Brewing and Goose Island. Unique ways to experience Chicago's brew culture include brewery tours, beer tastings, and Illinois Craft Brewers Guild events.

Insider tip:

Visit the Chicago Beer Festival in spring or fall to sample from 70+ breweries.

FAQs

What are some fun things to do in Chicago at night?

There are lots of things to do in Chicago at night. Evening escapades range from evening cruises to late-night drinks and rooftop dining. The 360 Chicago Observation Deck is a popular nighttime destination for views, while speakeasy bars are a fun place to go in Chicago to experience the city's past character.

Are there any fun day trips from Chicago that I should consider?

Take a trip to Will County, about an hour southwest of Chicago, to the 9,000-acre expanse of the Midewin National Tallgrass Prairie. Another popular day trip is to the Cave of the Mounds in Wisconsin, roughly a three-hour drive from Chicago, where you can explore unique geological formations. These are only a couple of the many day trips from Chicago.

What are some popular festivals or events in Chicago?

Chicago hosts a variety of festivals and events throughout the year. Lollapalooza, held every summer, is a major music festival that attracts top artists from around the world. The city holds a big St. Patrick's Day celebration with a parade and the dyeing of the Chicago River. The Chicago Air and Water Show is a free Chicago event that features aerial and watercraft displays.

What are some family-friendly fun activities to do in Chicago?

There are lots of fun experiences in Chicago for the whole family, from cycling around the city to exploring Chicago's parks and gardens. Millennium Park has a fountain to cool off in on hot days, the flower-filled Lurie Garden, and The Bean. Next door, there are play areas and a rock climbing wall at Maggie Daley Park. The Chicago Children's Museum and the Sloomoo Insitute are other fun things to do with kids in Chicago.

What are some fun outdoor activities to do in Chicago?

Chicago has many outdoor activities to enjoy, especially during the warmer months. Kayaking on the Chicago River or strolling around areas like Navy Pier or the 1.25-mile-long Chicago Riverwalk are excellent options. The Chicago Botanic Garden in Glencoe is perfect for a relaxing day, featuring beautiful gardens and walking paths, while Lincoln Park has numerous trails and picnic areas.