Chicago is a city of contrasts. It buzzes like a major metropolis but still carries the warm, welcoming charm of the Midwest. Here, towering skyscrapers meet peaceful beaches and lush green parks, which is why Chicago is often called the “City in a Garden.” Visitors feel at home almost immediately. Whether you’re wandering along the lakeshore or exploring downtown streets, the city offers endless experiences. If this is your first visit, make sure to include these things to do in Chicago in your travel plan. You’ll discover hidden gems and iconic attractions that make this city truly unforgettable.
1. Explore Chicago’s Millennium Park Campus
Millennium Park perfectly reflects the spirit of Chicago, offering endless attractions and activities. One of its most famous highlights is Cloud Gate, affectionately called “The Bean,” a must-see public artwork. Visitors love to snap creative photos here from every angle. Cool off at Crown Fountain, a shallow reflecting pool flanked by two digital towers displaying local faces. Summer brings outdoor dining near The Bean, while winter offers ice skating in the plaza. Free concerts, lively festivals, and movie nights at the Jay Pritzker Pavilion keep the energy alive year-round. For a peaceful retreat, stroll through Lurie Garden to spot birds, bees, and butterflies in a natural setting. It’s a serene escape right in the heart of downtown Chicago, making it one of the fun things to do in Chicago today.
Nearby, the Art Institute of Chicago ranks among the world’s top museums. From classic paintings to modern masterpieces, it offers something for every art lover. The Chicago Cultural Center amazes visitors with its massive Tiffany stained-glass dome, while evenings at Harris Theater for Music and Dance offer unforgettable performances. For family fun, Maggie Daley Park has lakefront climbing walls, mini golf, playgrounds, tennis courts, and seasonal ribbon skating. It’s also one of the things to do in Chicago with kids that adults will enjoy just as much.
2. Visit Chicago’s Iconic Navy Pier
Navy Pier is the ultimate lakeside playground. Whether traveling solo, with family, or with friends, it has something exciting for everyone. Glide across the sparkling waters on a scenic boat ride, savor local food favorites, or sip cocktails at the city’s largest rooftop bar with stunning lake views. During summer, watch fireworks every Wednesday and Saturday — best enjoyed from a cruise boat for an unforgettable experience. These fireworks are among the top things to do in Chicago, creating magical memories for all visitors.
The Centennial Wheel stands at the heart of the Pier, nearly 200 feet tall and inspired by the original Ferris wheel from Chicago’s World Fair. Climate-controlled gondolas offer breathtaking city views and perfect photo opportunities. Don’t miss free outdoor concerts, carnival rides, and indoor gardens that make every visit unique. For culture lovers, enjoy a play at Chicago Shakespeare Theater, live music at the Navy Pier Beer Garden, or hands-on exhibits at the Chicago Children’s Museum. Sunset cocktails at Offshore Rooftop offer views that will leave you speechless, making it a must-see for things to do in Chicago for adults.
Pro Tip: First time in Chicago? Make your trip effortless with a Big Bus Tour. Hop on, hop off, and explore the city’s top attractions at your own pace — an experience you’ll never forget.
3. Stroll the Chicago Riverwalk
The Chicago Riverwalk has something for everyone — whether you want to relax, party, or soak in the culture. Sip wine at riverside patios, unwind under sparkling trees, or paddle through the “skyscraper canyon” on a kayak. Take an architectural boat tour, join a lively tiki party boat, or enjoy pier fishing and birdwatching right in downtown Chicago — a unique blend of city life and nature. Art on theMART, the world’s largest video-projected artwork, adds a touch of creativity to your stroll. This vibrant pathway is also one of the free things to do in Chicago, offering unforgettable experiences without breaking the budget.
4. Chicago Theater Experiences You Can’t Miss
Chicago’s theater scene is bold, creative, and diverse. From Broadway In Chicago and Tony Award-winning shows to the famous improve hub The Second City and over 200 small storefront theaters, the city has something for everyone. Catch classic, experimental, or cutting-edge productions. For the best deals, visit during Chicago Theatre Week in February or grab half-price tickets through Hot Tix. Whether you’re an experienced theatergoer or trying something new, these performances rank among the top 10 things to do in Chicago for culture lovers.
5. Wrigley Field
Explore the legendary home of the Chicago Cubs on a Wrigley Field Tour. Opened in 1914, this iconic stadium is packed with over a century of baseball history. This year, the non-gameday Ivy Tour lets you snap photos in front of Wrigley Field’s famous ivy-covered walls. Sports fans and casual visitors alike can enjoy behind-the-scenes stories and experience the excitement that makes this one of the top things to do in Chicago Illinois.
6. Chicago Architecture Interiors Tour: Stunning Spaces
Step back into the Roaring Twenties on this unforgettable tour. Experience Prohibition-era Chicago with flappers, gangsters, and your lively host, Vito Valentino. Enjoy live music, delicious food, hilarious comedy, and Vito’s infamous bootleg hooch. Don’t forget the secret password once inside, the fun begins. This immersive experience is a top choice among things to do in Chicago for couples, offering both excitement and historical insight.
7. Explore Chicago’s Lively Neighborhoods
Chicago is a city of neighborhoods, each with its own culture, history, and vibe. Bronzeville and Chinatown showcase rich cultural heritage, Logan Square and Pilsen offer local flavors, and Lincoln Park or Garfield Park provide beautiful green spaces. Whichever area you choose, you’ll experience authentic Chicago life and see what it’s like to live like a local. Exploring neighborhoods is one of the things to do in Chicago today if you want to mix culture, food, and sightseeing all in one day.
8. Top Spots for Breathtaking Chicago Views
Chicago has two thrilling observation deck experiences atop its tallest skyscrapers. At Willis Tower’s Sky deck, step onto The Ledge a glass box extending over 1,300 feet above the city. Meanwhile, TILT at 360 CHICAGO leans you out over The Magnificent Mile, offering spectacular views of the city and Lake Michigan from 1,000 feet high. Both spots are perfect for photography lovers and anyone wanting to enjoy one of the top things to do in Chicago for adults.
9. Chicago Museum Campus
The Field Museum takes visitors on a journey through time, inspiring discovery and insight into nature and culture. With nearly 40 million specimens, including SUE, the world’s most complete Tyrannosaurus rex, there’s something fascinating for every visitor. Families, solo travelers, and school groups alike can spend hours exploring exhibits, making it one of the things to do in Chicago with kids that’s both educational and fun.
10. Chicago Crime and Rob Bus
Explore Chicago’s infamous mobster history, with names like John Dillinger and the legendary Al Capone. This bus tour, led by a knowledgeable guide, takes you to the exact spots where history unfolded. Sit back, relax, and enjoy this comfortable tour — perfect for any weather, with multiple departure times to fit your schedule. It’s a unique experience and one of the fun things to do in Chicago for history enthusiasts and curious travelers alike.
FAQ,s
1️⃣ Q: What are the must-visit attractions in Chicago?
A: Some must-visit attractions in Chicago include Millennium Park, The Art Institute of Chicago, Navy Pier, Willis Tower Skydeck, and the Field Museum.
2️⃣ Q: When is the best time to visit Chicago?
A: The best time to visit Chicago is from May to October when the weather is pleasant and outdoor activities like lakefront tours and festivals are in full swing.
3️⃣ Q: Are there family-friendly things to do in Chicago?
A: Yes, Chicago is very family-friendly with attractions like Shedd Aquarium, Lincoln Park Zoo, Maggie Daley Park, and interactive museums suitable for kids.
4️⃣ Q: How can I explore Chicago on a budget?
A: You can explore Chicago on a budget by visiting free attractions like Millennium Park, Chicago Cultural Center, Lincoln Park Zoo, and walking along the Chicago Riverwalk.
5️⃣ Q: What are some unique experiences in Chicago?
A: Unique experiences include taking an architecture river cruise, visiting the Skydeck at Willis Tower, exploring local food at Chicago’s deep-dish pizza restaurants, and attending live jazz or blues shows.
