Perched on the shores of Lake Michigan, Chicago is a city that buzzes with energy, creativity, and cultural depth. Known for its legendary skyline, world-class museums, vibrant food scene, and deep-rooted musical legacy, the Windy City is a must-visit for travelers of all kinds. Whether you’re visiting for the first time or rediscovering the city, here’s a curated guide to the The Best Things to Do in Chicago: A Guide to the Windy City’s — iconic landmarks, cultural highlights, outdoor adventures, and hidden gems that showcase the very best of this American metropolis.
1. Marvel at the Architecture on a Chicago River Cruise
Chicago is the birthplace of the modern skyscraper, and one of the best ways to admire its architectural wonders is from the water. An architecture river cruise offers a fascinating perspective of the city’s most iconic buildings—from historic towers to contemporary masterpieces. Knowledgeable guides bring the skyline to life with stories of innovation, vision, and design.
Why go: It's the city’s #1 rated tour experience.
Don’t miss: Twilight cruises for a magical view of the lit-up skyline.
2. Stroll Through Millennium Park and See “The Bean”
No trip to Chicago is complete without a visit to Millennium Park. At its heart is the world-famous Cloud Gate sculpture (affectionately known as “The Bean”), reflecting the skyline and drawing selfie-takers from around the globe. The park also features lush gardens, art installations, and free outdoor concerts during the summer.
Why go: A perfect mix of art, nature, and people-watching.
Pro tip: Visit early in the morning to beat the crowds.
3. Take in the Views from Skydeck Chicago or 360 CHICAGO
Chicago’s skyline is best appreciated from above. At Skydeck Chicago (Willis Tower), thrill-seekers can step out onto The Ledge — a glass balcony 1,353 feet in the air. Alternatively, 360 CHICAGO at the John Hancock Building offers stunning lake and skyline views, plus TILT, a moving glass platform that leans outward over the city.
Why go: Unbeatable panoramic views.
Insider tip: Time your visit around sunset for unforgettable scenery.
4. Explore the Art Institute of Chicago
Regularly ranked among the world’s top art museums, the Art Institute of Chicago houses a diverse collection spanning centuries and continents. Don’t miss Grant Wood’s American Gothic, Georges Seurat’s A Sunday on La Grande Jatte, and the museum’s extensive collection of Impressionist and Modern art.
Why go: It's a cultural cornerstone of the city.
Ideal for: Art lovers, history buffs, and curious minds.
5. Experience Chicago’s Deep-Dish Pizza and Food Scene
Chicago is a food lover’s paradise, from its iconic deep-dish pizza to its diverse and dynamic restaurant scene. Try a slice at Lou Malnati’s or Giordano’s, then branch out to discover everything from Michelin-starred fine dining to global street food in neighborhoods like Pilsen, Chinatown, and Little Italy.
Why go: Food is central to the Chicago experience.
Must-try: Italian beef sandwich, Chicago-style hot dog, and Garrett Popcorn.
6. Catch a Game or a Show
Chicago is a sports town through and through. Catch a Cubs game at Wrigley Field, one of the oldest ballparks in the country, or cheer for the Bulls, Bears, or Blackhawks depending on the season. Prefer the stage? The city also boasts a thriving theater scene, with productions at the Chicago Theatre, Steppenwolf, and Broadway in Chicago.
Why go: Sports and performance are woven into Chicago's cultural DNA.
Best for: Fans of live entertainment and electric atmospheres.
7. Walk the Lakefront Trail
Spanning 18 miles, the Lakefront Trail offers stunning views of Lake Michigan and access to some of the city’s top green spaces, including Grant Park, Lincoln Park, and Museum Campus. Whether you walk, jog, or bike, it’s one of the best ways to enjoy the outdoors in the city.
Why go: Scenic, peaceful, and active all in one.
Bonus: Stop by the beaches in summer for a true local experience.
8. Discover the Neighborhoods
Chicago’s strength lies in its neighborhoods, each offering a distinct cultural and culinary identity. Explore Wicker Park for indie boutiques and coffee shops, Logan Square for craft beer and nightlife, Hyde Park for history and museums, and Andersonville for charming Swedish roots and vintage shopping.
Why go: See the real Chicago beyond the tourist hubs.
Great for: Culture, local eats, and authentic city vibes.
9. Visit the Field Museum and Shedd Aquarium
Located on Museum Campus, these two institutions offer world-class exhibits for families and curious minds alike. See Sue the T. rex, one of the most complete Tyrannosaurus skeletons ever discovered, or get up close with sea otters, penguins, and sharks at Shedd Aquarium.
Why go: Fun, educational, and great for all ages.
Perfect for: Rainy days or family outings.
10. Listen to Live Blues or Jazz
Chicago’s musical legacy runs deep, especially in blues and jazz. Head to Buddy Guy’s Legends, Green Mill Cocktail Lounge, or Kingston Mines to hear talented performers carry on the city’s rich sonic tradition.
Why go: Feel the rhythm of the city in an intimate, historic setting.
Best time: Nighttime for the full experience.