Chicago, known as the Windy City, is one of the most vibrant and exciting destinations in the United States. From its stunning skyline to its deep-rooted history and world-class cuisine, Chicago offers something for everyone. Whether you’re visiting for the first time or you’re a local looking to explore new spots, this guide covers the top 5 must-visit places in Chicago in 2025.
Each of these locations showcases the city’s architecture, culture, and entertainment, making them essential stops on your Chicago itinerary.
Location: 201 E Randolph St, Chicago, IL 60602
No trip to Chicago is complete without a visit to Millennium Park, home to one of the city’s most famous landmarks—Cloud Gate, also known as “The Bean.” This giant reflective sculpture designed by Anish Kapoor is a favorite for photos and offers a stunning view of the Chicago skyline.
Apart from The Bean, Millennium Park hosts outdoor concerts, art installations, and the iconic Crown Fountain, where digital faces of Chicagoans spit water during summer. In the winter, the McCormick Tribune Ice Rink becomes a must-visit attraction for skaters.
Why Visit?
- Iconic Chicago landmark for photography
- Seasonal events like concerts and ice skating
- Free entry and a great spot for relaxing in the city
2. The Art Institute of Chicago
Location: 111 S Michigan Ave, Chicago, IL 60603
For art lovers, the Art Institute of Chicago is a world-renowned museum that houses over 300,000 artworks, including pieces from Van Gogh, Picasso, and Monet. One of its most famous works is “A Sunday Afternoon on the Island of La Grande Jatte” by Georges Seurat.
The museum also features modern and contemporary art, historical artifacts, and one of the best collections of impressionist paintings outside of France. The new Modern Wing, designed by architect Renzo Piano, adds a futuristic touch to the museum.
Why Visit?
- Home to masterpieces by famous artists
- One of the oldest and largest museums in the U.S.
- Located in the heart of Chicago’s cultural district
3. Willis Tower Skydeck & The Ledge
Location: 233 S Wacker Dr, Chicago, IL 60606
If you want breathtaking views of Chicago, head to the Skydeck at Willis Tower (formerly Sears Tower). Located on the 103rd floor, the Skydeck offers a 360-degree panoramic view of the city and beyond—on a clear day, you can see up to four states!
The most thrilling part of the experience is The Ledge, a glass observation box that extends four feet outside the building, allowing visitors to stand over 1,300 feet above ground.
Why Visit?
- One of the tallest observation decks in the world
- The Ledge provides an unforgettable experience
- Incredible photo opportunities of Chicago’s skyline
4. Navy Pier & Centennial Wheel
Location: 600 E Grand Ave, Chicago, IL 60611
Navy Pier is a lively waterfront attraction featuring restaurants, shopping, boat tours, and entertainment. The highlight of the pier is the Centennial Wheel, a 200-foot-high Ferris wheel offering stunning views of Lake Michigan and the Chicago skyline.
Navy Pier is also home to:
- Chicago Shakespeare Theater
- IMAX Theater
- Seasonal fireworks displays (summer and New Year’s Eve)
- Boat tours and dinner cruises along Lake Michigan
Why Visit?
- Family-friendly entertainment and activities
- Stunning waterfront views and boat tours
- One of the best places for food, fun, and relaxation
5. The Magnificent Mile & Chicago Riverwalk
Location: N Michigan Ave, Chicago, IL 60611
The Magnificent Mile is Chicago’s premier shopping and dining district, featuring luxury boutiques, flagship stores, and world-class restaurants. From high-end brands like Gucci and Louis Vuitton to iconic Chicago favorites like Garrett Popcorn, this area is a shopper’s paradise.
Just steps away from the Magnificent Mile is the Chicago Riverwalk, a beautiful pedestrian walkway along the Chicago River with:
- Outdoor restaurants and bars
- Kayaking and boat tours
- Public art displays and fountains
Why Visit?
- Perfect for shopping, dining, and sightseeing
- Enjoy a scenic walk along the Chicago River
- Great spot for both daytime exploration and nightlife
Bonus: Best Time to Visit Chicago
The best time to explore these attractions is during spring (April-May) and fall (September-October) when the weather is mild, and the city is full of festivals and events. If you visit in the winter, be prepared for snow, but also enjoy holiday lights, ice skating, and festive markets.
Conclusion
Chicago is a city that blends history, culture, architecture, and entertainment like no other. Whether you’re looking for stunning skyline views, world-class museums, exciting waterfront attractions, or high-end shopping, these top 5 places offer a perfect Chicago experience.
If you’re planning a trip to Chicago in 2025, make sure to include these must-visit destinations in your itinerary for an unforgettable experience!
