Page 23 - Events in Chicago in May 2026

Discover the wineries and rolling hills of Texas Hill Country on a full-day tour with hotel pickup from Downtown Austin or San Antonio. Explore the famous LBJ Ranch, stroll around historic Fredericksburg, and experience the magic and music of Luckenbach.

Experience Chicago’s legendary architecture from the best seat in the house: the river. Enjoy a comprehensive tour with a live fun guide as you navigate through the heart of the city covering all 3 branches of the Chicago River.

Cruise down the Chicago River and see the city’s most spectacular landmarks on a boat cruise with live, family-friendly commentary and a full-service bar on board.

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.

Experience Chicago's most prominent sights on this night tour with hotel transfers. Enjoy a skyline cruise of the Windy City, and head to the top of the Skydeck observation deck at Willis Tower.

Discover the delicious, multiregional cuisine on this wonderful Chinatown Food & Culture Tour. Expand your culinary horizons with unique dishes while learning about the fascinating Chinese culture.