Chicago’s 12 Best Things to Do in 2025 (Millennials + Gen Z)

Ready for the ultimate Chicago adventure? The Windy City is always buzzing with energy, and 2025 is one of the best years to experience it. From the iconic skyline views at the Willis Tower to the funky street art in Pilsen, Chicago has it all. If you’re a foodie craving deep-dish pizza, a thrill-seeker looking to ride the latest rollercoasters, or a history lover wanting to explore world-class museums, Chicago got you covered. Let’s get into these 12 must-do activities to experience the best of Chicago in 2025.

Best Places to Go in Chicago for Young Adults

Visiting Chicago? Take in stunning lakefront views at Navy Pier, grab a slice of deep-dish pizza at Lou Malnati’s Pizzeria, or enjoy breathtaking cityscapes from 360 CHICAGO. Sip cocktails with a view at LondonHouse Chicago, or catch a game at the iconic Wrigley Field. Whether you’re into food, nightlife, or sports, Chicago has plenty to offer.

1. Catch Thrills at Navy Pier

For an action-packed day in Chicago, Navy Pier is the place to be. Stretching 3,300 feet into Lake Michigan, this iconic spot is packed with rides, restaurants, and entertainment. The Centennial Wheel, standing 200 feet high, offers some of the best city views. If you’re into live performances, check out Chicago Shakespeare Theater, where world-class productions happen year-round. For a unique experience, take a Seadog Speedboat Tour for a high-energy ride along the shoreline.

Last summer, I visited Navy Pier on a whim and ended up staying until sunset, watching the fireworks light up the skyline. Whether you’re grabbing a bite at Giordano’s, exploring the Crystal Gardens, or hopping on a lake cruise, there’s always something happening here. Arrive early on weekends to avoid crowds, and if you’re visiting in the summer, don’t miss the Wednesday and Saturday night fireworks!

2. Savor the Flavor at Lou Malnati’s Pizzeria

No trip to Chicago is complete without deep-dish pizza, and Lou Malnati’s Pizzeria serves one of the best. With a recipe perfected since 1971, their signature pizza features a buttery crust, rich tomato sauce, and layers of gooey cheese. The Malnati Chicago Classic™, topped with lean sausage and extra cheese, is a must-try. Each bite is a reminder of why Chicago-style pizza is legendary.

The first time I tried Lou Malnati’s, I underestimated how filling one slice could be—I barely made it to a second! The Gold Coast and River North locations are great spots to sit down and enjoy, but if you’re in a hurry, carryout and delivery are solid options. Expect a wait during peak hours, but trust me—it’s worth it. If you want to mix it up, their buttery-crust thin-crust pizza is also fantastic.

3. Try Yoga With a View at 360 CHICAGO

Imagine doing yoga 1,000 feet above the city—that’s exactly what you get at 360 CHICAGO Observation Deck. Located on the 94th floor of 875 N Michigan Avenue (formerly John Hancock Center), this experience combines breathtaking skyline views with a guided yoga session. Whether you’re a beginner or a pro, stretching while overlooking Lake Michigan and the Chicago skyline is an unforgettable way to start your day.

I joined a morning class once, and watching the sunrise while holding a warrior pose was surreal. After class, you can stick around to explore the observation deck or test your courage on TILT, a glass platform that leans you forward over the edge of the building. Book your spot early since yoga sessions sell out fast, and bring a light jacket—it gets chilly up there!

4. Sip Cocktails High Above the City at LondonHouse Chicago

For one of the best rooftop views in Chicago, head to LondonHouse Chicago. Located on the 22nd floor of a historic building on Michigan Avenue, this rooftop bar delivers panoramic views of the city, the Chicago River, and Lake Michigan. Whether you’re sipping a handcrafted cocktail at LH Rooftop or enjoying the River Vista Afternoon Tea, the atmosphere is always top-tier.

I grabbed a seat here on a summer evening, and watching the sunset reflect off the skyscrapers was next-level. The signature drinks are as good as the view—try the LondonHouse Old Fashioned or the LH Margarita. Dress smart-casual, as it’s a popular nightlife spot, and make a reservation in advance if you want a prime seat on the terrace. If you prefer a quieter vibe, head to LH on 21, their stylish indoor lounge.

5. Cheer Like a Local at Wrigley Field

There’s nothing like the energy of a Chicago Cubs game at Wrigley Field. Built in 1914, it’s one of the most historic and beloved ballparks in the country. From the ivy-covered outfield walls to the roaring crowd in the bleachers, Wrigley has an old-school charm that makes every game feel special. Even if you’re not a die-hard baseball fan, the atmosphere, classic ballpark snacks, and live music in Wrigleyville make it a must-do experience.

I went to my first Cubs game on a sunny afternoon and instantly got hooked on the excitement. The 7th-inning stretch singalong and Wrigleyville bar scene are just as fun as the game itself. If tickets are pricey, check out the rooftop seating at nearby buildings for a unique view. And if you visit off-season, take a stadium tour to explore the dugouts and press box.

6. Cruise and Schmooze on Spirit of Chicago

For a night out with skyline views and nonstop entertainment, hop aboard the Spirit of Chicago Dinner Cruise. This Lake Michigan cruise includes a buffet-style dinner, live DJ, and dancing, all set against Chicago’s stunning waterfront. The outdoor deck is perfect for soaking in the city lights and landmarks like Navy Pier and the Willis Tower. If you time it right, you can even catch the fireworks on Wednesday and Saturday nights.

I went on a cruise with a group of friends, and between the music, food, and insane city views, it was one of the best nights we had in Chicago. The vibe is casual but fun, and people of all ages get into the dance party by the end of the night. Dress to impress (smart casual works), book your tickets early, and don’t forget to step outside for that Instagram-worthy skyline shot!

7. Dive into Discovery at Shedd Aquarium

Step into an underwater world at Shedd Aquarium, home to over 32,000 aquatic animals from across the globe. From beluga whales and sea otters to colorful coral reef fish and sharks, this spot is both educational and mesmerizing. One of the highlights is the Wild Reef exhibit, where you can watch massive sharks glide overhead. The Aquatic Presentation is another must-see, featuring trained dolphins and sea lions in action.

The first time I visited, I found myself completely hypnotized by the Jellyfish Exhibit, where glowing, otherworldly creatures float gracefully in dark-lit tanks. If you want a more interactive experience, sign up for an animal encounter and get up close with a penguin or beluga whale. Buy tickets in advance to skip long lines, and if you visit in the summer, go early to beat the crowds.

8. Discover Art at the Museum of Contemporary Art

If you love modern and experimental art, the Museum of Contemporary Art (MCA) Chicago is the place to be. Located near the Magnificent Mile, this museum features rotating exhibits of photography, sculpture, paintings, and interactive installations. Past exhibitions have included Andy Warhol, Takashi Murakami, and Kerry James Marshall, so expect bold, thought-provoking work. The museum also has a performance space, sculpture garden, and a fantastic gift shop for unique souvenirs.

I visited an exhibition here that had an entire room filled with mirrors and lights, and it felt like stepping into another dimension. One of the best parts of MCA is that it’s never the same twice, thanks to its ever-changing exhibits. Visit on a Tuesday for free admission, and don’t miss Marisol, the café with a sleek design and great coffee. If you’re looking for something artsy but approachable, MCA is a must.

9. Rock Out at The House of Blues

For an unforgettable live music experience, The House of Blues Chicago delivers on every level. Located near the Chicago River in Marina City, this legendary venue hosts rock, blues, jazz, and hip-hop artists in an intimate yet high-energy setting. The walls are covered in vibrant folk art, and the sound system is top-notch, making every show an immersive experience. If you’re a brunch fan, their Sunday Gospel Brunch features live music and a massive Southern-style buffet.

I caught a surprise set here one night, and the energy was unreal—people dancing, singing along, and just vibing with the music. The venue isn’t huge, so you always feel close to the stage. Check their lineup ahead of time, as they book everything from big-name artists to indie bands. Arrive early to grab a good spot, and don’t skip their Southern-inspired cocktails—the Hurricane is a solid pick!

10. Zip Through the Sky at 360 CHICAGO

If you thought a sky-high view was exciting, wait until you try TILT at 360 CHICAGO. Located on the 94th floor of 875 N Michigan Avenue, this observation deck offers panoramic views of the city, Lake Michigan, and beyond. But the real thrill? TILT—an enclosed glass platform that tilts forward at a 30-degree angle, giving you a heart-pounding view straight down. If you love adrenaline rushes, this is for you.

I was hesitant at first, but once I leaned into TILT, it was surprisingly smooth—until I looked down! It’s an experience you won’t find anywhere else in Chicago. If you prefer a more relaxed visit, head up during sunset for golden-hour views or stop by BAR 94 for a cocktail with a skyline backdrop. Buy tickets online to save time, and if you’re feeling brave, go for the Sky High Combo, which includes both TILT and a drink.

11. Gaze at Stars at Adler Planetarium

For a cosmic escape, head to Adler Planetarium, the first planetarium in the U.S. and still one of the best. Whether you’re learning about black holes, exploring the Mars Rover simulation, or catching a space show in the Grainger Sky Theater, every visit is packed with awe-inspiring astronomy experiences. The museum’s location on Northerly Island offers some of the best lakefront views of the Chicago skyline, making it a great place to visit day or night.

One of my favorite visits was during an Adler After Dark event—where the museum turns into a 21+ space party with drinks, DJs, and telescope viewings. Even on regular days, the Doane Observatory lets you look through one of the largest public telescopes in the Midwest. Check their schedule for special events, and if you’re visiting during summer, go at night to see the Chicago skyline light up.

12. Solve Mysteries at The Escape Game Chicago

For an interactive and fast-paced challenge, gather your crew and head to The Escape Game Chicago. Located in River North, this immersive experience puts you in a themed room where you have 60 minutes to solve puzzles, crack codes, and escape. The games range from breaking out of prison to stopping an art heist, with realistic sets and mind-bending clues that make you feel like you’re in a movie.

I did the Gold Rush escape room with friends, and just when we thought we had it all figured out, a hidden door opened! It’s one of the best team activities in Chicago, whether you’re visiting with friends or family. If you’re new to escape rooms, the staff helps you choose a difficulty level so it’s fun without being impossible. Book ahead, as weekend slots fill up fast, and arrive 15 minutes early to get your game face on.

Frequently Asked Questions About Fun Activities in Chicago for Young Adults

Curious about what Chicago for young adults has to offer? Our FAQs have got you covered with all the insider tips and must-knows!

What makes Chicago a great destination for young adults?

Chicago is a vibrant city teeming with activities that cater to young adults. From its dynamic music scene and diverse nightlife to its rich cultural offerings like museums and theaters, there’s always something exciting to explore. The city’s blend of urban charm and lakeside beauty offers a unique backdrop for a variety of experiences, making it an ideal destination for those seeking adventure, entertainment, and cultural enrichment.

What are some popular activities for 20 year olds in Chicago?

Activities for 20 year olds in Chicago are diverse and thrilling. This age group often enjoys exploring the city’s lively music venues, like The House of Blues, or engaging in interactive experiences like The Escape Game Chicago. Outdoor enthusiasts can bike along the Lakefront Trail, while art lovers can immerse themselves in the contemporary collections at the Museum of Contemporary Art. The city’s diverse neighborhoods also offer a chance to experience different cultures and cuisines.

What’s Chicago famous for?

Chicago is renowned for its impressive architecture, deep-dish pizza, and jazz and blues heritage. The city boasts iconic structures like Willis Tower and the Cloud Gate sculpture in Millennium Park. Chicago’s culinary scene is also a highlight, with its famous Chicago-style hot dogs and diverse dining options. Additionally, the city’s rich history in jazz and blues music continues to thrive in its many live music venues.

Are there any notable bars for young adults in Chicago?

Chicago has some of the best bars in Chicago for young adults, offering a range of atmospheres from trendy rooftop bars to cozy speakeasies. Popular spots include the lively atmosphere of Three Dots and a Dash, known for its tiki-themed cocktails, and the chic ambiance of The Signature Room at the 95th, offering stunning city views. For those who enjoy craft beers, the city’s numerous breweries and taprooms provide a taste of local flavors. It’s also one of the best places to go in Chicago for couples where the ambiance, food, and views come together to create a magical experience.

Is Chicago good for shopping?

Chicago is a fantastic city for shopping, offering everything from high-end boutiques on the Magnificent Mile to unique finds in local neighborhoods like Wicker Park and the Loop. The city is home to major department stores, designer outlets, and independent shops, catering to a wide range of styles and budgets. Whether you’re looking for the latest fashion trends or one-of-a-kind gifts, Chicago’s shopping scene has it all.

How do I spend my day in Chicago?

Spending a day in Chicago can be an exciting mix of sightseeing, dining, and entertainment. Start with a visit to a famous attraction in Chicago like the Art Institute of Chicago or the Skydeck at Willis Tower. Enjoy lunch at a local eatery, then spend the afternoon exploring neighborhoods like Lincoln Park or the Gold Coast. End your day with a show at a theater in the Theater District or with live music at a venue like The House of Blues.

What are some unique things to do in Chicago for young adults?

For young adults looking for unique experiences, Chicago offers a range of options. Engage in an immersive art experience at places like the Museum of Contemporary Art or explore the city’s vibrant street art scene. For a taste of adventure, try kayaking on the Chicago River or join a bike tour through the city’s historic neighborhoods. The city’s diverse cultural festivals throughout the year also offer a unique way to experience Chicago’s rich heritage.

What are the best ways to experience Chicago’s nightlife?

Experiencing Chicago’s nightlife is a must, with options ranging from jazz clubs and rooftop bars to dance clubs and comedy shows. The city’s music scene is vibrant, offering everything from blues and jazz to indie and electronic music. For a more laid-back evening, enjoy a cocktail at a rooftop bar with city views or laugh the night away at a comedy club like The Second City. Chicago’s nightlife truly has something for every taste.

Final Thoughts on Chicago Attractions for Young Adults

Chicago is a city bursting with energy and possibilities, especially for young adults looking for adventure and new experiences. From the towering skyscrapers and bustling streets to the serene parks and lakefront, the city offers a diverse range of activities. This makes it one of the best places to travel in the US for young people.

Whether you’re into music, art, food, or outdoor adventures, there’s no shortage of fun stuff to do in Chicago for young adults. Each neighborhood tells its own story, inviting you to explore and create memories. Chicago is a place where every visit can be different, yet always exciting. So, pack your sense of adventure and get ready to discover all the fun and wonders this vibrant city has to offer.