28 Things to Do in Chicago: Discover the Best Attractions and Hidden Gems
Introduction
Chicago, affectionately known as the “Windy City,” is one of the United States’ most vibrant and historic cultural hubs. Located on the shores of Lake Michigan, Chicago is famed for its stunning architecture, rich history, world-class museums, and dynamic food scene. Whether you enjoy panoramic skyline views, serene parks, or arts and culture, Chicago has something to offer every type of traveler.
In this article, we’ll explore the 28 best things to do in Chicago—from iconic spots like Millennium Park and Navy Pier to hidden gems like the Garfield Park Conservatory and unique attractions such as the International Museum of Surgical Science. Whether you’re planning a weekend getaway or a week-long vacation, these attractions showcase the best of Chicago’s charm and diversity. Let’s embark on an unforgettable journey through the heart of this iconic American city!
1. Millennium Park & Cloud Gate (“The Bean”)
No visit to Chicago is complete without a visit to Millennium Park. As the city’s central hub and one of its most iconic landmarks, Millennium Park spans 25 acres and is home to several attractions. The most famous of these is Cloud Gate, affectionately known as “The Bean.” Designed by British artist Sir Anish Kapoor, this mesmerizing polished steel sculpture reflects both the Chicago skyline and the crowds that gather beneath it, offering a truly interactive visitor experience. The mirrored surface creates the perfect backdrop for selfies, making it one of the most photographed spots in the city.
Beyond The Bean, the park features other notable highlights such as the Crown Fountain, a digital art installation involving two towering glass blocks, and the Jay Pritzker Pavilion, an open-air concert venue designed by architect Frank Gehry. Lurie Garden, a serene garden space featuring native prairie flowers and paths, provides a quiet retreat within the bustling center of the city.
Millennium Park often hosts free cultural events, concerts, and outdoor movie screenings, making it a lively destination for both locals and tourists.
2. Navy Pier
Stretching over 3,300 feet into the waters of Lake Michigan, Navy Pier is one of Chicago’s premier family-friendly attractions. Originally opened in 1916 as a shipping and recreational facility, the pier has evolved into a bustling entertainment hub featuring a broad array of activities and attractions.
Families flock to Navy Pier for its variety of boat rides, including architectural tours, sightseeing cruises, and pirate-themed excursions. The Centennial Wheel, a massive Ferris wheel that offers spectacular views of the Chicago skyline and Lake Michigan, represents a classic pier experience. On summer evenings, the skies above Navy Pier are regularly lit up with fireworks, adding an extra layer of magic to each visit.
If you’re looking for a cultural experience, Navy Pier is home to the Chicago Shakespeare Theater, where award-winning productions take place year-round. You’ll also find several restaurants, gardens, and seasonal attractions like the Winter Wonderfest during the holiday season. Whether you’re seeking casual waterfront dining, a thrill ride on the Wave Swinger, or some quiet time by the pier’s stunning Polk Bros Park, Navy Pier is a timeless Chicago destination.
3. Art Institute of Chicago
A must-see for any art lover, the Art Institute of Chicago is among the world’s most renowned art museums. Located adjacent to Millennium Park, the museum boasts an impressive collection covering thousands of years of human creativity and featuring works by some of history’s most revered artists.
Inside its vast galleries, you’ll find masterpieces by iconic artists such as Vincent van Gogh, Claude Monet, Pablo Picasso, and Georges Seurat. In fact, the museum houses one of the most significant collections of Impressionist and Post-Impressionist paintings outside of Paris. Major works include Grant Wood’s American Gothic and Edward Hopper’s Nighthawks.
The museum doesn’t just focus on European masters—it also has rich collections of American art, contemporary works, and ancient artifacts from global civilizations. Special exhibitions often highlight emerging artists or significant global movements, so there’s always something new to see.
Set against the beautiful backdrop of Grant Park, the Art Institute’s location makes it a convenient stop and ideal for pairing with other local attractions. Both serious art connoisseurs and casual museum-goers will find something to marvel at in this jewel of Chicago’s cultural scene.
4. Willis Tower Skydeck
For breathtaking, panoramic views of Chicago and beyond, head to the Skydeck located on the 103rd floor of Willis Tower—formerly known as the Sears Tower. As one of the tallest buildings in the Western Hemisphere, Willis Tower’s Skydeck offers a unique vantage point for taking in sprawling views across multiple states on a clear day.
The highlight of the experience is The Ledge, a series of glass boxes that extend outside the building. With glass floors, walls, and ceilings, standing on The Ledge feels like floating above the bustling city nearly 1,353 feet below. It’s an exhilarating photo opportunity and not for the faint-hearted!
Visitors can also find interactive exhibits throughout the Skydeck, providing fun facts and insights into the history, architecture, and culture of Chicago. If you’re timing your visit right, catching a sunset from the Skydeck will deliver one of the most spectacular views imaginable, with the Chicago skyline silhouetted against the fading light over Lake Michigan.
5. Chicago Riverwalk
Stretching along the banks of the Chicago River, the Chicago Riverwalk offers a scenic pedestrian path with spectacular views of the city’s iconic architecture. Spanning 1.25 miles from Lake Michigan to the heart of downtown, it’s a favorite spot for walking, jogging, or simply enjoying a relaxed meal by the water.
The Riverwalk is also a hub for culinary and cultural experiences. Along its stretch, you’ll find a variety of public art installations and outdoor dining options, ranging from casual cafes to fine dining restaurants. Be sure to check out Art on theMART, a large-scale digital art projection that transforms the façades of downtown buildings into stunning displays each evening.
Additionally, several boat tours depart from the Riverwalk area, offering up-close views of Chicago’s famous architectural landmarks such as Tribune Tower, Marina City, and Willard’s historic Wrigley Building. Whether you’re taking a leisurely stroll, grabbing a drink at one of the many riverside bars, or embarking on a boat tour, the Riverwalk offers stunning views and plenty to explore.
6. Shedd Aquarium
For an underwater adventure, the Shedd Aquarium is one of the nation’s largest and most impressive aquariums. Its collection spans marine habitats from around the world, featuring thousands of aquatic creatures from sharks to penguins, jellyfish, and Amazonian fish.
Popular exhibits include the Wild Reef, showcasing sharks and other predators of the coral reef, and the Caribbean Reef, where you can watch colorful fish, rays, and green sea turtles swim past in a 90,000-gallon circular tank. The aquarium also hosts dynamic animal encounters, allowing visitors to get up-close and personal with beluga whales, dolphins, and otters.
7. Field Museum of Natural History
The Field Museum is one of Chicago’s great cultural institutions, especially known for its vast natural history exhibits. It houses SUE, the largest and most complete Tyrannosaurus rex skeleton ever discovered, as well as Máximo, a life-sized replica of a Titanosaur. The museum’s collection covers the history of our planet from fossils to ancient human civilizations.
8. Adler Planetarium
Founded in 1930, the Adler Planetarium was the first planetarium in the Western Hemisphere and remains an essential destination for anyone fascinated by space exploration. It features interactive exhibits that educate visitors on the wonders of the universe. Immersive sky shows within the Grainger Sky Theater let visitors travel the stars without ever leaving the ground.
9. Museum of Science and Industry
The Museum of Science and Industry is one of the largest science museums in the world. It features myriad interactive exhibits on electricity, weather, transportation, space exploration, and more. Highlights include the gigantic U-505 Submarine used in World War II and a recreated 1930s coal mine experience that showcases life underground.
10. Lincoln Park Zoo & Alfred Caldwell Lily Pool
The Lincoln Park Zoo is a Chicago gem and one of the last free major zoos in the U.S. It is home to a wide variety of animals, ranging from big cats and penguins to critically endangered species like the Western Lowland Gorilla. Located nearby, the Alfred Caldwell Lily Pool offers a peaceful retreat surrounded by lush greenery and calm waters.
11. The Magnificent Mile
The Magnificent Mile is a shopper’s paradise. This mile-long stretch along Michigan Avenue offers a mix of top-tier luxury brands, historic landmarks like the Water Tower, and world-class dining. The Magnificent Mile is not just about shopping; it’s also a culinary and architectural tour in its own right.
12. 360 Chicago Observation Deck at John Hancock Center
Located atop the John Hancock Center, the 360 Chicago Observation Deck offers panoramic views over the city skyline and Lake Michigan. For thrill-seekers, the TILT attraction allows visitors to lean outwards from the 94th floor, providing a unique and heart-pounding view down Michigan Avenue.
13. Chicago Architecture River Cruise
Chicago is known for its stunning skyline and groundbreaking architecture, and there’s no better way to experience it than on the Chicago Architecture River Cruise. Guides provide a detailed commentary on the city’s architectural history during this boat tour, highlighting iconic buildings like the Marina City Towers and Tribune Tower.
14. The 606 Elevated Trail
The 606, a 2.7-mile-long elevated park trail constructed on a former railway line, is a favorite among locals for biking, running, and walking. Stretching through several Chicago neighborhoods like Wicker Park and Bucktown, the trail is lined with public art installations and offers scenic urban views.
15. Wrigley Field & Gallagher Way
Wrigley Field is not only home to the Chicago Cubs, but it’s also one of the oldest major league ballparks in the U.S. A trip to Wrigleyville, the neighborhood bustling with bars and eateries, is a quintessential Chicago experience. Nearby Gallagher Way, adjacent to the ballpark, showcases a bustling square with family-friendly activities, community events, and live music performances.
Hidden Gems & Unique Experiences
16. Garfield Park Conservatory
Known as the “landscape art under glass,” the Garfield Park Conservatory is one of the largest and most striking botanical conservatories in the U.S. Its greenhouses are a lush escape, filled with tropical plants, cacti, orchids, and ferns from around the world.
17. Robie House by Frank Lloyd Wright
Designed by the legendary architect Frank Lloyd Wright, the Robie House in Chicago’s Hyde Park neighborhood is lauded as one of the most significant works of 20th-century architecture. The masterpiece exemplifies Wright’s renowned Prairie School design, emphasizing horizontal lines and natural materials.
18. The DuSable Black History Museum & Education Center
For those interested in African American history, the DuSable Black History Museum offers a deep dive into civil rights movements, African heritage, and Chicago’s important role in Black history and culture.
19. Oz Park & Lincoln Park Conservatory
Oz Park is a family-friendly outdoor space dedicated to characters from The Wizard of Oz, featuring life-size bronze statues of Dorothy, Toto, and the Tin Man. Nearby, the Lincoln Park Conservatory provides exquisite garden and tropical greenhouse experiences.
20. Smart Museum of Art at University of Chicago
The Smart Museum of Art, located on the University of Chicago campus, features diverse art collections spanning centuries, with a focus on modern and contemporary movements.
Outdoor Activities
21. Lakefront Trail
For stunning views of both Lake Michigan and the city skyline, the Lakefront Trail is an 18-mile stretch perfect for bikers, runners, and walkers. Along the trail, you’ll pass beaches, parks, and cultural institutions like the Museum Campus.
22. Maggie Daley Park & Skating Ribbon
Adjacent to Millennium Park, Maggie Daley Park offers a large playground with twists and turns, vibrant rock climbing walls, and the Skating Ribbon—an ice-skating path that loops around the park in winter.
23. North Avenue Beach & Oak Street Beach
Looking to relax by the water? North Avenue Beach and Oak Street Beach are popular lakefront spots with sandy shores, volleyball nets, and stunning views of Chicago’s skyline. These beaches are perfect for swimming, sunbathing, and enjoying water sports.
Cultural & Historical Attractions
24. Chicago Cultural Center & Tiffany Dome
The Chicago Cultural Center is a building rich in history, offering free exhibits, performances, and architectural tours. The standout feature is the breathtaking Tiffany Dome, the largest of its kind, composed of thousands of pieces of stained glass.
25. National Museum of Mexican Art in Pilsen
Located in the Pilsen neighborhood, the National Museum of Mexican Art houses one of the most comprehensive collections of Mexican art in the U.S., celebrating both ancient and modern Mexican culture.
Family-Friendly Attractions
26. Chicago Children’s Museum at Navy Pier
Located on Navy Pier, the Chicago Children’s Museum offers a range of interactive exhibits designed to spark creativity and curiosity among young visitors, from crafting and storytelling to hands-on science experiments.
27. Maggie Daley Park Climbing Wall & Playgrounds
Beyond the skating ribbon, Maggie Daley Park also features state-of-the-art playgrounds tailored for kids of various age groups and a climbing wall perfect for both beginners and experienced climbers, offering fun and challenge in a lakefront setting.
Unusual Attractions
28. International Museum of Surgical Science
For an offbeat yet fascinating experience, visit the International Museum of Surgical Science. Housed in a historic mansion, this museum features exhibits on the history of surgery, with original surgical instruments, artifacts, and anatomical models from around the world.
FAQs Section: Common Questions About Visiting Chicago
1. What is the best time to visit Chicago?
The best time to visit Chicago is during the spring (April-May) and fall (September-November) when the weather is mild, and crowds are fewer. Summer (June-August) offers plenty of outdoor events, while winter (December-February) features holiday festivals and ice-skating.
2. How do I get around in Chicago?
Public transportation is the most convenient way to get around. The Chicago Transit Authority (CTA) operates buses and trains (the “L”). Other options include Divvy bikes or walking, especially in downtown areas. Rideshare services like Lyft and Uber are also popular.
3. What are some free things to do in Chicago?
Enjoy Millennium Park and visit The Bean, stroll along the Chicago Riverwalk and Lakefront, see animals at the Lincoln Park Zoo, explore parks like Maggie Daley Park, or visit the Chicago Cultural Center with its Tiffany Dome.
4. What food is Chicago famous for?
Chicago is famed for its deep-dish pizza (try places like Giordano’s or Lou Malnati’s), Italian beef sandwiches (Al’s Beef and Portillo’s), and Chicago-style hot dogs (no ketchup!).
5. Is it safe to visit downtown Chicago?
Yes, downtown Chicago (The Loop) is generally safe, especially in tourist areas like Millennium Park and Navy Pier. However, as with any city, be mindful of your surroundings, especially at night, and keep your belongings secure.
Conclusion: Why You Should Visit Chicago Now!
Chicago’s reputation as one of America’s greatest cities is well deserved. Its rich architectural history, world-class museums, breathtaking skyline, and deep cultural lineage make it a destination that appeals to all age groups and interests. Whether you’re marveling at Cloud Gate in Millennium Park, shopping along the Magnificent Mile, or soaking in views from the Skydeck at Willis Tower, Chicago offers moments of awe and inspiration at every corner.
Outdoor enthusiasts will relish the miles of green space and trails that wind along Lake Michigan, while foodies can indulge in culinary experiences ranging from classic deep-dish pizza to Michelin-starred fine dining. Families can delight in endless attractions like Navy Pier, the Shedd Aquarium, and multiple world-renowned museums.
But beyond its major landmarks, what truly makes Chicago special is its sense of community, the warmly welcoming spirit of its people, and its ability to blend innovative modernity with proud tradition. Whether you’re coming for a weekend or longer, the Windy City promises experiences—both iconic and unexpected—that will stay with you long after you leave. Now is the perfect time to embrace all that Chicago has to offer!
