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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 the360 Chicago Observation Deck.

  • Discover a true Chicago icon when you visit the world-famousWillis Tower.

  • Visit Al Capone’s former haunts (and learn about the city’s sordid past) on analternative history tour.

  • See where the Cubs made World Series history on awalking tour of Wrigleyville.

  • Sip acclaimed Illinois wines aboard aLake Michigan boat tour.

  • Use aChicago Explorer Passto 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 hop-on hop-off bus tour.

  • Get to know Chicago’s spooky side during aHalloween-themed bike tour.

  • Step back in time to the Roaring Twenties at aspeakeasy-themed dinner show.

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6 Tours and Activities | All Chicago Tours

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Chicago Crime and Mob Tour

Chicago Crime and Mob Tour

star-4
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
  • Taking safety measures
From
$45.00
From
$45.00
Taking safety measures

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
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
  • Taking safety measures
From
$38.85
From
$38.85
Taking safety measures

Skip the Line: Tommy Gun's Garage Dinner and Show Ticket

Skip the Line: Tommy Gun's Garage Dinner and Show Ticket

star-4.5
Transport yourself back in time to Chicago’s roaring twenties at Tommy Gun’s Garage, a unique speakeasy dinner show in the Windy City. Say the password at the front door and then step into an era of mob guys and flappers, Broadway tunes by Cole Porter and George Gershwin and lively dances like the Charleston. This gut-busting show, full of song, dance and audience participation, is sure to please.
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  • 3 hours
  • Free Cancellation
From
$67.00
From
$67.00

Go Chicago Explorer Pass with SkyDeck and 360 Chicago

Go Chicago Explorer Pass with SkyDeck and 360 Chicago

star-4.5
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Go Chicago Explorer Pass saves you up to 45 percent on regular ticket prices. Create your own sightseeing itinerary by choosing 2, 3, 4, or 5 attractions, tours, and activities from among more than 30 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 (purchased by December 31) are valid for two year 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
$66.00
From
$66.00

Fright Hike: Chicago Halloween Bike Tour

Fright Hike: Chicago Halloween Bike Tour

star-5
Pedal through Chicago’s scary heritage with a 3-hour Halloween bike tour that includes hauntings, tragedies and overflowing cemeteries. Experience the creepiest parts of the city as you follow your professional actor guides through the Halloween streets, and watch them bring Chicago’s ghosts to life. Learn about the infamous ‘Resurrection Mary,’ figure out why the Levee District is so famously haunted, and hear the story of H.H. Holmes, Chicago’s most notorious serial killer.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$0.00
From
$0.00
Taking safety measures

360 CHICAGO Observation Deck (Hancock Center) Sun & Stars Admission

360 CHICAGO Observation Deck (Hancock Center) Sun & Stars Admission

star-4.5
If you can’t decide whether you prefer clear daytime or twinkling nighttime city views, this is the ideal activity for you. The Sun and Stars admission ticket to the 360 Chicago Observation Deck allows you to visit twice, so you can come once in the day, once at night. The deck is one of the highest points in Chicago, and this ticket allows you to see the stunning panoramic views in two completely different ways.
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  • 1 to 2 hours
  • Free Cancellation
  • Taking safety measures
From
$28.50
From
$28.50
Taking safety measures