27 Fun Things to Do in Chicago for an Unforgettable Experience
Known for its bold architecture, rich cultural heritage, and stunning location on the shores of Lake Michigan, Chicago is one of the most dynamic cities in the U.S. Travelers flock to Chicago to enjoy its myriad attractions, from world-class museums and lively neighborhoods to its iconic skyline and deep-rooted sports culture. Whether you’re visiting for a weekend or planning a longer stay, there are endless ways to experience the Windy City. In this guide, we’ll walk you through 27 fun things to do in Chicago—activities that cater to all types of visitors, whether you’re an art lover, history buff, foodie, nature enthusiast, or adrenaline seeker. Let’s dive right in to uncover the best ways to make the most out of your Chicago adventure!
1. Explore Millennium Park and Cloud Gate (The Bean)
One of Chicago’s most iconic and frequently visited landmarks, Millennium Park is a heart-stealer for both tourists and locals. Dominating the park is Cloud Gate, affectionately referred to as “The Bean” due to its bean-like reflective shape. Designed by British-Indian artist Anish Kapoor, this giant stainless-steel sculpture offers stunning reflections of the Chicago skyline, making it a popular spot for taking photos. But The Bean isn’t the only notable feature.
You can also appreciate the artistic simplicity of Crown Fountain, whose two towering LED glass blocks project images of Chicagoans while spouting water, offering a refreshing splash zone during warm months. For nature lovers, Lurie Garden provides a tranquil escape with native plants and walking paths right in the middle of the city. Don’t miss the Jay Pritzker Pavilion, an open-air concert venue designed by Frank Gehry, providing a blend of architectural beauty and live music performances that captivate visitors during Chicago’s summer months.
2. Take an Architecture River Cruise
Chicago’s rich architectural history is a story best told from the water. An Architecture River Cruise is a must-do activity to get a close-up view of some of the city’s most famous buildings while learning about the city’s design evolution. Chicago is the birthplace of the modern skyscraper, and its skyline is a canvas that features world-renowned buildings like the Willis Tower, John Hancock Center, and Marina City.
You’ll hear fascinating stories about these structures and others along the way, offering a glimpse into the minds of the visionary architects who shaped the city. Several companies offer these educational yet leisurely cruises.
The Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady sets the gold standard, led by knowledgeable guides who provide insightful commentary. Another popular option is Wendella Boat Tours, which has operated on the river for nearly 90 years and offers multiple cruise options, including sunset tours for those who want to relax while taking in the spectacular evening views. Regardless of which you choose, the architecture cruise provides a unique perspective of Chicago’s skyline, marrying history, design, and stunning visuals.
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3. Visit Navy Pier
Stretching out into Lake Michigan, Navy Pier serves as a year-round playground for people of all ages. Originally opening in 1916, the Pier has transformed into a major tourist destination with a variety of activities and places to explore. One of the most prominent features is the Centennial Wheel, a 200-foot-tall Ferris wheel that provides passengers with breathtaking views of both the city skyline and the expansive lake. Navy Pier is also home to several theaters, with regular performances including those by Chicago Shakespeare Theater.
Families with young children will enjoy the Chicago Children’s Museum, a treasure trove of interactive exhibits ranging from art studios to waterplay. Navy Pier additionally offers countless dining options—whether you’re interested in a quick bite aboard one of the many beacheside food stalls or a sit-down meal at a waterfront restaurant like Riva Crabhouse. Of course, no trip to Navy Pier is complete without experiencing one of its summer fireworks shows, boat tours, or festival events, many of which take place regularly throughout the year. Whether you’re with family, friends, or solo, Navy Pier promises an unforgettable day brimming with attractions.
4. Admire Art at The Art Institute of Chicago
The Art Institute of Chicago is a must-visit destination for art lovers. Home to one of the largest and most impressive collections in the world, the museum houses more than 300,000 works spanning centuries, cultures, and artistic movements. Strolling through its vast galleries, you’ll spot iconic masterpieces like Grant Wood’s American Gothic, Georges Seurat’s A Sunday on La Grande Jatte, and Vincent van Gogh’s Self-Portrait. Another crowd favorite is the institute’s extensive Impressionist and Post-Impressionist collection, where works by Claude Monet and Edgar Degas grace the walls in vivid strokes.
Throughout the museum, visitors also encounter a plethora of artifact collections centered on ancient civilizations, medieval Europe, Asian arts, and African textiles, offering something for every kind of art buff. The building is a masterpiece in its own right, with striking Beaux-Arts style architecture that melds seamlessly with its 2009 Modern Wing expansion designed by Renzo Piano. Located in Grant Park, the museum also provides a peaceful outdoor space to complement your cultural experience indoors. Whether it’s your first visit or your hundredth, the Art Institute continually evolves, adding new exhibits and installations to explore.
5. Stroll Along the Chicago Riverwalk
Lounging along the banks of the Chicago River, the Chicago Riverwalk offers a perfect mixture of scenic beauty, urban exploration, and leisure activities. Stretching approximately 1.25 miles from Lake Shore Drive to Lake Street, the Riverwalk serves as a pedestrian haven that offers diverse opportunities to experience city life. Dotted along its length are vibrant eateries and outdoor bars such as City Winery and Tiny Tapp, providing charming spots to grab a drink or meal while soaking in views of the river and the skyline above.
Public art installations also pepper the route, making it a cultural experience as much as a recreational one. For those seeking something more aquatic, kayaking tours and boat rentals are available, allowing you to paddle through the city’s watery arteries for a unique vantage point of Chicago’s architectural wonders. If you’d rather cruise, water taxis and architectural tours operate along the Riverwalk. Whether roaming with friends or enjoying a peaceful solo stroll, the Riverwalk is a relaxing yet thrilling way to experience downtown Chicago and see the city from a new angle.
6. Experience Skydeck Chicago at Willis Tower
Ever wonder what it feels like to stand over 1,300 feet above the ground? That thrill can be found at Skydeck Chicago, located on the 103rd floor of the iconic Willis Tower. As one of the highest observation decks in North America, Skydeck offers panoramic views extending up to four states on a clear day. The most exhilarating feature, however, is The Ledge, a series of glass-bottomed boxes that extend four feet out from the tower.
Stepping onto The Ledge feels like you’re floating above the city, allowing nervy visitors to gaze directly down at the streets below. For the history buffs, there’s plenty to learn about Willis Tower’s (formerly Sears Tower) architectural innovations. Across the observation floor, interactive touchscreens allow visitors to explore the landmarks and notable sights visible from the Skydeck. Whether you visit at sunrise to catch the first rays of light hitting the city or at sunset to watch the city lights twinkle into view, a trip to Skydeck is one of those bucket-list experiences that define a trip to Chicago.
7. Enjoy Nature at Lincoln Park Zoo
Tucked in the middle of sprawling Lincoln Park, the Lincoln Park Zoo is one of the oldest zoos in North America, dating back to 1868. What makes it extra special? It’s completely free to the public, making it a beloved attraction for families and kind-hearted nature lovers alike. Covering 35 acres, the zoo is home to about 1,300 animals from all over the world. Whether you’re in the mood to watch chimpanzees at play in the Regenstein Center for African Apes or catch a glimpse of an Amur tiger prowling in the Kovler Lion House, there’s no shortage of fascinating wildlife to observe.
Lincoln Park Zoo also places a strong emphasis on conservation and animal welfare, often featuring interactive and educational programs where visitors can learn more about the animals and the efforts being made to protect their habitats. Adjacent to the zoo is the equally beautiful Lincoln Park Conservatory, a lush space crawling with exotic plants and flowers, offering both relaxation and education. Both outdoor landmarks are easily walkable and provide a perfect pairing with the zoo experience.
8. Discover Science at The Field Museum
For history buffs, biology lovers, and geology enthusiasts alike, The Field Museum offers a treasure trove of fascinating exhibits that celebrate the natural world and human history. Opening its doors in 1893 after the World’s Columbian Exposition, the museum is best known for being home to Sue, the largest and most complete Tyrannosaurus rex skeleton ever discovered. But dinosaurs are merely one aspect of this sprawling institution’s allure. Journey through time as you explore galleries dedicated to everything from ancient Egyptian mummies to the story of the planet’s evolution.
One eye-catching exhibition, Inside Ancient Egypt, transports you to the tombs of pharaohs with its 23 human mummies, reconstructions of ancient temples, and other sacrificial offerings. The museum also provides hands-on learning with the Evolving Planet exhibit, charting life’s development, and The World of Gemstones, showcasing dazzling minerals and gems. Located on Chicago’s Museum Campus, alongside the Shedd Aquarium and Adler Planetarium, The Field Museum is an unmissable educational experience for both children and adults, allowing you to immerse yourself fully in the diversity of our planet and human history.
9. Relax at Grant Park and Buckingham Fountain
Known affectionately as Chicago’s front yard, Grant Park is an expansive green space located in the city’s downtown area that welcomes both locals and visitors seeking a respite from the urban landscape. The star of the park is the Buckingham Fountain, one of the largest fountains in the world, with a stunning daily water show featuring synchronized lights and music during evening presentations (spring through autumn).
Visitors to the park can relax by the fountain, take strolls along the tree-lined paths, and explore various gardens. It’s also a hotspot for seasonal events, including the famous Taste of Chicago food festival and summer concerts like Lollapalooza. Bordering other top attractions like The Art Institute and Millennium Park, Grant Park is a serene yet central place to spend time outdoors, making it a tranquil yet vital element of any itinerary for fun things to do in Chicago.
10. Take a Ride on the Centennial Wheel at Navy Pier
Navy Pier’s Centennial Wheel stands as one of Chicago’s most famous attractions, offering panoramic views stretching across Lake Michigan and the downtown skyline. The wheel reaches heights of nearly 200 feet, which gives riders a bird’s eye view that is particularly dazzling at night when the wheel lights up and the city sparkles against the lake’s tranquil waters. Each enclosed gondola is climate-controlled, making it an enjoyable ride year-round, regardless of the weather.
A nostalgic attraction, rooted in Chicago’s love for Ferris wheels—remember, the original Ferris wheel debuted at the 1893 World’s Fair in Chicago—the Centennial Wheel is a delightful experience that enhances any trip to Navy Pier. Whether you’re riding it in the day or at twilight, the Wheel offers unparalleled views and a distinctly Chicago experience.
11. Visit Shedd Aquarium
Chicago’s Shedd Aquarium is one of the most prestigious aquariums in the world, home to thousands of marine species that range from adorable sea otters to mesmerizing jellyfish. For a close-up view of aquatic animals, head to the aquarium’s Oceanarium, a showcase of beluga whales, dolphins, and sea lions. This vast indoor aquarium presents diverse marine habitats, with recreated environments representing various ecosystems from around the world, ranging from the Amazon River Basin to the deep ocean.
The Wild Reef exhibit immerses visitors in coral reefs full of vibrant fish life and even shark tanks—perfect for those who are fascinated by the ocean’s most formidable predators. Guests of all ages keep engaged with interactive learning exhibitions, such as touch pools where kids can pet stingrays and starfish. The Shedd also doubles as a venue that holds frequent events, from live-dive shows to spotlighted talks with marine biologists, making it an enriching and fascinating stop for any type of visitor.
12. Explore Adler Planetarium
For those intrigued by the wonders of space, the Adler Planetarium is a celestial haven you don’t want to miss. Located on Museum Campus with stunning views of Lake Michigan and the downtown skyline, Adler offers immersive planetarium shows, hands-on exhibits, and opportunities for engaging with astronomy. The historic Atwood Sphere allows visitors to peer into a model of the night sky as it appeared in 1913, while the interactive Community Design Lab lets curious minds tinker with models and simulations related to space technologies. Live telescope viewings are also available, affording guests a framed and magnified glimpse into outer space wonders right from the city.
13. Wander Through Maggie Daley Park
For a family-friendly day out in Chicago, head over to Maggie Daley Park, adjacent to Millennium Park. This destination was purposely designed to cater to kids and visitors of all ages, as it features adventurous rock climbing walls, a whimsical playground, and a skating ribbon that transforms into an ice-skating wonderland during the winter. The miniature golf course features Chicago-themed obstacles that fully tie the experience back to the city’s local charm. Whether you are a child or just a child-at-heart, Maggie Daley Park provides ample space for outdoor fun, making it a perfect reprieve from the bustling city streets while still keeping you right in the heart of downtown Chicago.
14. Shop Along The Magnificent Mile
Shoppers rejoice! If you love indulging in some retail therapy, The Magnificent Mile (also known as Michigan Avenue) is Chicago’s premier shopping strip. Home to luxury brands like Louis Vuitton, Gucci, and Tiffany & Co., it also offers a range of other shopping delights, from high-end retail at Water Tower Place to recognizable global brands like H&M and Zara. Along with shopping, the Magnificent Mile is dotted with architectural landmarks such as the historic Chicago Water Tower and prominent restaurants where you can take a break to sample Chicago-style deep-dish pizza or globally inspired cuisine.
Attractions like 360 CHICAGO (updated John Hancock observation deck) and museums such as the Museum of Contemporary Art are just steps away, making the area brimming with both buying and browsing opportunities. Whether it’s a casual walk, a window-shopping venture, or a blow-out shopping spree, exploring The Magnificent Mile is a Chicago bucket-list experience for those embracing fashion and architecture in harmony.
15. Visit Wrigley Field for a Cubs Game or Tour
A visit to Wrigley Field is a pilgrimage for every baseball fan. As one of the oldest ballparks in Major League Baseball, this historic stadium hosts Chicago Cubs games, bringing together locals and visitors for an all-American pastime in an atmosphere steeped in history and tradition. If your visit doesn’t coincide with a game, tours of the iconic stadium are still a must! Wander through the locker rooms, peek inside the press box, and learn about the ballpark’s fascinating history, including the origin of its ivy-covered outfield wall. Whether you’re a die-hard Cubs fan or just love the historic charm of classic American sporting culture, Wrigley Field is both a ballpark and a local legend you’ll want to experience.
16. Relax at Oak Street Beach or North Avenue Beach
If you’re looking for a quintessential Chicago summer experience, make sure to relax at Oak Street Beach or North Avenue Beach along Lake Michigan. Nestled between the bustling downtown and the serene unlimited horizon of Lake Michigan, both urban beaches offer the perfect atmosphere to swim, sunbathe, or participate in some beach volleyball. For those visiting Oak Street Beach, you’re a stone’s throw away from the iconic Gold Coast, while North Avenue Beach offers amenities like kayak rentals and even an entertainment-packed bar modeled after a lakefront boat. With stunning views of the skyline, the beaches provide a delightful mix of urban energy and a laidback beach vibe, perfect for the hot summer months.
17. Marvel at Views from 360 CHICAGO Observation Deck (John Hancock Center)
Rise 1,000 feet above Chicago to experience one of the city’s most thrilling viewpoints. Located on the 94th floor of the John Hancock Center, 360 CHICAGO offers near-panoramic, floor-to-ceiling views of not only the Chicago skyline, but you can also see deep into Lake Michigan and, on clear days, all the way to four surrounding states. But for daredevils looking for an extra adrenaline rush, TILT will give you a heart-pounding experience. This glass-encased platform tilts visitors forward over Michigan Avenue, providing the sensation of hovering above the city streets. Along with unparalleled views, the observation deck’s cafes provide a peaceful spot to sip a drink while soaking in the extraordinary perspective. Whether you visit during the day to take in Lake Michigan’s blues or at sunset when the skyline is bathed in golden hues, 360 CHICAGO brings an unmissable experience to any itinerary.
18. Explore Chicago History Museum
The Chicago History Museum provides a comprehensive overview of this storied city’s past, from its earliest days to its modern-day evolution. Featuring exhibits like the Great Chicago Fire of 1871 and early developments in transportation (hello, the “L” train!), this museum offers an engaging deep dive into the social, cultural, and architectural milestones that make Chicago unique. A don’t-miss section of the museum includes artifacts from President Abraham Lincoln, given Illinois’ moniker as “the Land of Lincoln.”
19. Walk Through Garfield Park Conservatory & Lincoln Park Conservatory
Escape into a world of greenery at two of Chicago’s magnificent conservatories: Garfield Park Conservatory and Lincoln Park Conservatory. Both are free to visit and offer a peaceful oasis within the city where nature lovers can roam among exotic plants, blooming flowers, and innovative floral arrangements housed in impressive glass structures. The Garfield Park Conservatory is often referred to as “landscape art under glass” due to its vast indoor collections, while Lincoln Park Conservatory offers a smaller but equally enchanting array of botanical beauty.
20. Take a Segway Tour Along Lakefront Trail or Through Downtown Chicago
For visitors looking to zoom through town without having to constantly walk, Segway tours offer an exhilarating mode of transport to explore downtown and the nearby Lakefront Trail. With expert guides leading the way, visitors can learn about the rich history of the city while gliding effortlessly on two wheels alongside sweeping lake views or zipping between fascinating architectural landmarks in the Loop. Riders receive the added entertainment of a fresh, immersive experience that captures the essential sights of the city.
21. Visit The Museum of Science & Industry (MSI)
The Museum of Science & Industry (MSI) is one of the most interactive museums in Chicago, perfect for travelers of any age. Located in Jackson Park, MSI makes science engaging with hands-on exhibits and life-sized displays that cater to the curious spirit. One highlight: the museum celebrates historical achievements related to space exploration, computing technologies, and more. The U-505 Submarine Exhibit is particularly notable, bringing visitors on a tour through a real German U-Boat captured during World War II. From storm simulators to interactive jet planes and even a walk-through of a working coal mine, the variety here makes MSI a must-do for fun science learning.
22. Attend a Show at The Second City Comedy Club (Family-Friendly Shows Available)
Known as the training ground for comedy legends like Tina Fey, Bill Murray, and Steve Carell, attending a show at The Second City Comedy Club is a quintessential Chicago experience. While some shows offer biting political satire and other adult-themed humor, there are plenty of family-friendly performances, particularly the hilarious improv shows, that cater to younger audiences. The intimate venue provides a sense of closeness between audience and performers, enhancing the laughter-filled moments as you witness the birth of tomorrow’s top comedians.
23. Take an Urban Kayak Tour on The Chicago River or Lake Michigan
For those seeking a bit of active adventure, urban kayaking lets you explore Chicago from its waterways. Whether you are paddling on the calm stretches of the Chicago River or navigating the waves of Lake Michigan, urban kayaking offers a new way to see the towering skyscrapers and bustling city streets from a peaceful vantage point on the water. Guided tours allow you to paddle through iconic spots, like the Riverwalk, along side historic architecture that blends together Chicago’s past and present.
24. Explore Navy Pier’s Crystal Gardens Indoor Botanical Garden (Free Admission)
The Crystal Gardens at Navy Pier is a beautiful hidden gem that provides free, year-round access to a serene indoor greenhouse brimming with tropical plants and dancing fountains under six-stories of glass. The gardens are the perfect spot to take a relaxing break from the many energetic activities at Navy Pier, offering a quiet space amid the greenery for pictures, contemplation, and delightful walks.
25. Visit Peggy Notebaert Nature Museum (Great for Kids)
For hands-on learning about nature and the environment, the Peggy Notebaert Nature Museum in Lincoln Park is a wonderland perfect for younger visitors. The butterfly haven, filled with live fluttering butterflies, is the star of the show, captivating children’s imaginations. Interactive exhibits educate kids about local ecosystems, conservation efforts, and the joys of the natural world.
26. Go Indoor Skydiving at iFLY Chicago (Great for Teens & Tweens)
Buckle up for sky-high thrills—without the actual airplane! At iFLY Indoor Skydiving, you’ll experience the sensation of free-fall in a completely safe environment. Ideal for adventure-seeking teens and tweens looking for something unique, this one-of-a-kind experience is great for beginners and offers plenty of excitement without ever leaving the ground.
27. Take a Bike Ride Along The Lakefront Trail (Bike Rentals Available)
For an eco-friendly, scenic way to explore the lakeside, hop on a bike and soar along the Lakefront Trail. Spanning 18 miles, this waterfront path offers a ride that takes you from Chicago’s downtown core all the way up to its northern and southern neighborhoods, with jaw-dropping views of the water and skyline accompanying you along the entire route. Bike rentals are widely available, so you can set your own pace and explore attractions like Grant Park, the Field Museum, and the city’s many beaches found along Lake Michigan.
FAQs Section
What are some free things to do in Chicago?
Chicago offers plenty of free attractions, including Millennium Park, Lincoln Park Zoo, Grant Park, and walking along the Chicago Riverwalk. Both Garfield Park Conservatory and the Lincoln Park Conservatory offer free admission, as does access to the outdoor segments of Navy Pier.
What is there to do in Chicago with kids?
Chicago is bursting with family-friendly activities, such as exploring the Shedd Aquarium, checking out the city views from the Centennial Wheel, running wild at Maggie Daley Park, and learning through nature at the Lincoln Park Zoo and Peggy Notebaert Nature Museum.
What are some unique things to do in Chicago?
For something different, take an architecture boat tour, go kayaking on the Chicago River, or test your bravery at Skyline decks like Skydeck Chicago and 360 CHICAGO’s TILT. Don’t forget about experiences like the indoor skydiving at iFLY or attending an improv comedy show at The Second City.
What is the best time of year to visit Chicago?
Summer (June to August) offers the best weather for outdoor activities like kayaking, biking, beach visits, and festivals. Fall brings cooler weather with fewer crowds, and the winter offers an entirely different yet magical experience with events like Christkindlmarket and ice skating at Maggie Daley Park.
How can I get around in Chicago without a car?
Chicago’s extensive public transportation network is easy to navigate, with options like buses, “L” trains, and even water taxis. You can also choose bike rentals or walk between most of the major downtown attractions.
What are some outdoor activities in Chicago?
Visitors can enjoy biking along The Lakefront Trail, taking a boat or kayak tour, sunbathing at North Avenue Beach, or merely soaking in the sights at the array of city parks like Grant Park and Millennium Park.
Is Navy Pier worth visiting?
Absolutely! With attractions like the Centennial Wheel, numerous dining options, live performances, and a number of family-friendly activities, Navy Pier offers something for everyone. Additionally, the free Crystal Gardens and rotating seasonal events make it a must-visit on your Chicago itinerary.
Conclusion
In a city that presents a harmonious blend of history, nature, and urban culture, the 27 activities outlined cover just a fraction of what Chicago offers to its visitors. With iconic sites, immersive history, and vast recreational opportunities, it’s a city where you can find the perfect balance between high-flying adventure and peaceful reflection. Whether you’re marveling at world-class art at the Art Institute, soaking in stunning panoramic views from Skydeck Chicago, relaxing on sun-soaked beaches, or shopping along The Magnificent Mile, Chicago offers an unforgettable experience that’s sure to delight. One trip simply won’t be enough to uncover all that this magnificent city has in store, but hopefully, this guide has given you an excellent head start on making the most out of your visit.
