Things to Do in Chicago This Fall
Fall is a wonderful time to visit Chicago. Crisp breezes and golden leaves lend the Windy City a romantic, autumnal ambiance, but it’s still warm enough to enjoy open-air bus tours, cruises along Lake Michigan and the Chicago River, and engaging walking tours. Here’s what to do during your fall visit to the Windy City.
Explore the city by boat, and catch glimpses of its most striking buildings, on an architecture river cruise.
Admire stunning city views from the lofty heights of the 360 Chicago Observation Deck.
Discover a true Chicago icon when you visit the world-famous Willis Tower.
Visit Al Capone’s former haunts (and learn about the city’s sordid past) on an alternative history tour.
See where the Cubs made World Series history on a walking tour of Wrigleyville.
Sip acclaimed Illinois wines aboard a Lake Michigan boat tour.
Use a Chicago Explorer Pass to craft your own sightseeing itinerary (and visit the city’s top museums and attractions).
Make the most of your time in the Windy City on a h op-on hop-off bus tour.
Get to know Chicago’s spooky side during a Halloween-themed bike tour.
Step back in time to the Roaring Twenties at a speakeasy-themed dinner show.