Events in Chicago in October 2025

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.

Soar to heights of nearly 200 feet over Navy Pier, with unparalleled, 360-degree views of Chicago and Lake Michigan. Experience the iconic Chicago skyline.

Save up to 50%* on admission to 2-10 top Chicago attractions with Go City's Explorer Pass. Choose from over 30 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.

Enjoy a fully immersive experience at the Museum of Ice Cream, delivering joy and entertainment for the whole family. Savor signature ice cream flavors and sweet treats as you explore the museum.

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 30+ 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.