Chicago, a city renowned for its vibrant culture, rich history, and diverse attractions, offers a plethora of activities that cater to all interests and preferences. For tourists and locals alike, here are some fun, entertaining, and unique things to do in Chicago, especially during the first week of May 2025.
To start your day, consider visiting the Chicago Cultural Center for the "Under The Picasso Noontimes" event, which takes place on Fridays, including May 3, 2025. This free event features live music performances under the iconic Picasso sculpture in the Daley Civic Center Plaza, providing a perfect blend of art and music.
For those interested in architecture, the Chicago River: 1.5-Hour Guided Architecture Cruise is a must-do. This cruise, available throughout May, offers a detailed look at Chicago's architectural landmarks and historical buildings along the Chicago River. Alternatively, you can opt for the 45-Minute Family-Friendly Architecture River Cruise, which is more suited for families with children.
If you're looking for outdoor adventures, the Spring Flower Show, which is ongoing in early May, is a great place to visit. Held at various locations, this show showcases the beauty of spring with a variety of flowers and plants on display. Another outdoor highlight is Buckingham Fountain in Grant Park, which will turn on its water display on May 10, 2025. This fountain is one of the largest in the world and features a spectacular light and music display at dusk.
Art enthusiasts will find plenty to appreciate in Chicago. The Art Institute of Chicago, one of the top art museums in the country, boasts a vast collection that includes works by Monet, Van Gogh, and an extensive collection of miniature rooms. The museum is open daily from 9 AM to 5 PM.
For a unique cultural experience, take the Chicago: Taste of Chinatown Food Walking Tour. This tour allows you to explore the culinary delights of Chinatown, sampling local delicacies and learning about the history and culture of the area.
Sports fans can enjoy a tour of Wrigley Field, the historic home of the Chicago Cubs. These tours provide access to the press box, dugout, and other behind-the-scenes areas, offering a glimpse into the ballpark's rich baseball heritage.
Music lovers should check out the various concerts and performances happening in May. While specific dates and artists may vary, Chicago is known for its vibrant music scene, with venues like the Chicago Theatre and the United Center hosting top acts throughout the year.
For an elevated view of the city, visit the SkyDeck at the Willis Tower or the Navy Pier Centennial Wheel. The SkyDeck features a glass-floored ledge and interactive displays, while the Navy Pier Centennial Wheel offers panoramic views of the city and Lake Michigan.
Food experiences are also plentiful in Chicago. In addition to the Taste of Chinatown tour, you can explore the city's culinary scene with the Chicago: Mob and Crime Bus Tour, which includes stops at local eateries and delis, or visit the historic Magnificent Mile, known for its upscale dining and shopping.
The Field Museum, located on the Museum Campus, is another must-visit attraction. Here, you can see Maximo, the Titanosaur, the largest dinosaur that ever lived, along with other interactive educational exhibits on ancient cultures and extinct species.
Finally, for a blend of history and entertainment, take the Chicago: Mob and Crime Bus Tour, which delves into the city's infamous crime history, or visit Millennium Park, which features serene gardens, interactive fountains, and iconic sculptures like Cloud Gate.
Whether you're interested in art, music, sports, or outdoor adventures, Chicago has something for everyone, making it a city that is both entertaining and enriching to visit.