Top Sights & Attractions in Chicago: 5 Must-See Highlights
Explore the Best Things To Do in Chicago With Drives & Detours’ Guide to the City’s Top Attractions—From World-Class Museums and Skyline Views to Lakefront Landmarks and Iconic Urban Experiences You Won’t Want To Miss
The Windy City is full of architectural brilliance, artistic innovation, and Midwestern charm — Benjamin R / Unsplash
Few cities blend architectural brilliance, artistic innovation, and Midwestern charm quite like Chicago. The Windy City offers a skyline that inspires awe, food that feeds the soul, and lakefront views that seem endless, whether it’s your first visit or your fifth.
While Drives & Detours self-guided tours spotlight Chicago’s lesser-known corners, no trip is complete without checking off a few of the city’s most iconic landmarks. These are our five can’t-miss experiences.
Here’s your guide to the top five attractions in Chicago—plus a few insider tips to make your visit unforgettable.
1. Millennium Park & Cloud Gate—The Bean
Cloud Gate—better known as The Bean—has come to define Chicago’s image — Dulcey Lima / Unsplash
If there’s one image that defines modern Chicago, it’s Cloud Gate, the gleaming mirrored sculpture affectionately nicknamed The Bean.
Designed by artist Anish Kapoor, this stainless-steel marvel perfectly captures the city skyline—and your reflection—in its curved surface. It’s playful, photogenic, and symbolic of Chicago’s bold artistic spirit.
Cloud Gate anchors Millennium Park, a sprawling urban oasis that forms part of the larger Grant Park complex along Michigan Avenue.
But the Bean is just the beginning. The park also features the futuristic Jay Pritzker Pavilion, where free concerts and cultural events fill the air with music, the interactive Crown Fountain, where digital faces spill water in a blend of technology and play, and the peaceful Lurie Garden, a botanical retreat in the heart of downtown.
In winter, the park’s McCormick Tribune Ice Rink turns into one of Chicago’s most beloved seasonal attractions—especially with the skyline glittering behind you.
Visit early morning or at dusk for the best light and fewer crowds. And don’t rush—Millennium Park rewards those who linger.
2. The Art Institute of Chicago
The Art Institute of Chicago is one of the world’s greatest museums and is full of works by the masters — Walter Martin / Unsplash
Just steps from Millennium Park sits one of the world’s greatest art museums—the Art Institute of Chicago. Housing masterpieces from every corner of the globe, it’s often ranked the number one attraction in Chicago—and for good reason.
Inside, you’ll find everything from Monet’s luminous water lilies to Van Gogh’s The Bedroom and Grant Wood’s American Gothic.
The museum’s Impressionist and Post-Impressionist collections are world-renowned, but its reach extends into modern and contemporary works, ancient artifacts, photography, design, and beyond.
The Art Institute’s Beaux-Arts architecture is impressive in its own right, with grand stone lions guarding the entrance on Michigan Avenue. Once inside, the museum’s modern wing, connected by a glass bridge, provides stunning views of Millennium Park and the city skyline.
Download the museum’s app or pick up a map to plan your route through its vast galleries. Give yourself at least two hours here if possible—you’ll want the time to soak it all in.
3. Willis Tower Skydeck & The Ledge
The Willis Tower dominates Chicago’s skyline, and offers some of its most thrilling experiences — Margo / Unsplash
The Willis Tower (formerly the Sears Tower) was the tallest building in the world when it opened in 1973—and it remains one of Chicago’s defining icons.
At 1,450 feet, the tower still dominates the skyline, drawing millions of visitors each year to its Skydeck on the 103rd floor.
The highlight? The Ledge—four glass boxes that extend four feet out from the tower’s face, letting you stand (or sit, if you dare) directly above the city.
The view stretches up to four states on a clear day, taking in Illinois, Indiana, Wisconsin, and Michigan. It’s one of those only-in-Chicago experiences that’s equal parts thrilling and unforgettable.
Inside the Skydeck lobby, exhibits trace Chicago’s architectural evolution, offering context before your ascent. But it’s that moment you step into the glass box—heart pounding, camera ready—that you’ll remember most.
Go early in the morning or just before sunset for fewer crowds and jaw-dropping light. Skip-the-line tickets are well worth it during peak season.
4. The Chicago Riverwalk
Chicago Riverwalk is a seamless blend of nature, architecture, and urban energy — John Benitez / Unsplash
Flowing right through the heart of downtown, the Chicago Riverwalk is one of the city’s most beautiful and walkable public spaces—a seamless blend of nature, architecture, and urban energy.
Stretching along the south bank of the Chicago River, this pedestrian promenade transforms what was once an industrial corridor into a lively waterfront lined with cafes, public art, and open-air patios that invite you to linger and take in the view.
As you stroll, you’ll pass distinct “rooms”—from quiet garden zones to bustling restaurant terraces—each offering a unique perspective of the river and skyline. Locals gather here for after-work drinks, morning jogs, and sunset strolls, while visitors marvel at how the city’s legendary skyscrapers seem to rise right from the water’s edge.
Along the way, you’ll find spots like City Winery, The Northman Beer & Cider Garden, and O’Brien’s Riverwalk Café, all perfect places to sip something cold while boats glide by. Public art installations and informational plaques also dot the path, adding layers of culture and history to the experience.
Travelers consistently say that the Riverwalk is among the top things to do in Chicago, and it’s easy to see why—it captures everything the city does best: bold design, scenic beauty, and a sense of community that thrives outdoors.
Visit during the golden hour before sunset, when the light reflects off the glass towers and the river turns to liquid gold. For an even deeper experience, pair your walk with a stop at one of the riverfront bars or patios to watch the city come alive after dark.
5. Navy Pier & the Centennial Wheel
Navy Pier is Chicago’s playground, park, and promenade — Gautam Krishnan / Unsplash
Stretching nearly half a mile into Lake Michigan, Navy Pier is one of Chicago’s most beloved entertainment destinations. Equal parts playground, park, and promenade, it’s home to a mix of restaurants, theaters, museums, and lakefront views that make it a natural stop for travelers of all ages.
At its center rises the Centennial Wheel, a 200-foot Ferris wheel that offers sweeping, climate-controlled views of the skyline and lake. Whether you’re riding in daylight or after dark, the panorama is spectacular—especially when the pier lights up for summer fireworks shows.
Navy Pier is also the starting point for many boat tours, including lake cruises and the aforementioned architecture tours. Inside, you’ll find the Chicago Children’s Museum, Chicago Shakespeare Theater, and a rotating calendar of festivals and events that keep the energy buzzing year-round.
Time your visit around sunset, then stay for dinner or drinks at one of the pier’s waterfront restaurants for unbeatable views.
Plan Your Perfect Chicago Experience
Start with Chicago’s top attractions, and then let curiosity take you — Unsplash
Chicago is a city best explored at your own pace. Start with these top attractions, then let curiosity lead you into neighborhoods like Pilsen, Lincoln Park, or Wicker Park, where local culture and cuisine shine brightest.
Whether you’re standing atop Willis Tower, gazing into The Bean, or cruising down the river, Chicago rewards explorers who look up—and look closer.
So grab your camera, lace up your walking shoes, and get ready to experience Chicago’s top attractions like never before.
If you’re planning a Drives & Detours adventure, these landmarks create a perfect foundation for your route—giving you the best of both worlds: the big-name must-sees and the chance to discover what lies between them.
Discover Chicago at Your Own Pace With Drives & Detours
Drives & Detours shares the rich cultural history of Chicago and guides you to must-see sights and hidden treasures —aveedibya-dey / Unsplash
Experience Chicago on your terms with Drives & Detours’ self-guided tours. Designed to be flexible, informative, and fully accessible offline, these tours let you explore one of America’s greatest cities at a pace that suits you.
Purchase your tour online ahead of time or download the app and start your adventure whenever it works for you.
Each tour shares the rich cultural history of Chicago and guides you to must-see sights and hidden treasures across the city.
With Drives & Detours, you won’t miss the little-known spots and local favorites that make Chicago truly special.
