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Things to Do in Chicago This Fall

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.

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

3 Tours and Activities

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Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1145
Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$46.00
From
$46.00

Chicago Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architecture River Cruise

star-5
7004
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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  • 1 hour
  • Free Cancellation
From
$40.33
From
$40.33

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

star-4
218
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Chicago Explorer Pass by Go City saves you up to 40 percent off compared to buying individual attraction tickets. Create your own sightseeing itinerary by choosing 2, 3, 4, 5, 6 or 7 attractions, tours, and activities from among more than 25 top sites, including SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two years from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 60 days and/or the remaining number of attraction choices purchased.
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  • 60 days
From
$59.00
From
$59.00