Events in Chicago in May 2026

Save up to 50%* on admission at 2 to 7 top Chicago attractions with Go City's Explorer Pass. Choose from over 35 options including 360 Chicago, Shoreline River Cruise, Skydeck Chicago, and much more.

Embark on a history-based guided walking tour and discover the stories of Chicago’s gangsters and ghosts. Learn about the city’s darker side and creepy past as you explore the Chicago Loop district.

Explore Chicago on a Crime and Mob Bus Tour. Escape into the city's underworld and learn about infamous gangsters and mobsters like Al Capone and John Dillinger.

Save up to 50%* on unlimited entry to 35+ Chicago attractions with Go City. Visit 360 Chicago and Skydeck Chicago for the views, explore Shedd Aquarium, enjoy an Architectural River Cruise and more!

Sample Chicago’s four favorite food groups – pizza, hot dogs, brownies, and beer – on this city bike tour. Tour Chicago's famous neighborhoods and top attractions, day and night tour routes.

Skip the ticket purchase desk to enjoy the best panoramic views of Chicago, 94 stories above the Windy City. Enjoy stunning lake views and close-up vistas of Chicago’s amazing skyscrapers.

Explore Chicago at your own pace with a Big Bus hop-on hop-off tour or sunset tour. See Chicago's landmarks including Willis Tower, Navy Pier, and Magnificent Mile from an open-top double-decker bus.

Experience Cincinnati and the Ohio River like never before on a boat cruise. Enjoy a delicious buffet dinner aboard the boat while gazing at the city skyline with friends or family.

Explore SEA LIFE Michigan Aquarium and marvel at an array of sea animals from around the globe. Discover more than 5,000 fish, rays, sea horses, and jellies, and surround yourself with sharks and sea turtles.

Purchase an unlimited ride wristband for a full day of rides at America’s first indoor Nickelodeon theme park, located inside the Mall of America, Minnesota where it is always 72 degrees and sunny.