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United States · fall (Sep-Nov)

Fall in Chicago: Autumn Foliage Tours & Activities

Lakefront runs, deep-dish lunches, river architecture cruises at golden hour. Foliage day trips, harvest food tours, autumn walking guides and quieter shoulder-season experiences in Chicago — the sweet spot between summer crowds and winter chill.

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Autumn experiences in Chicago

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1h 15m

Spectacular Lake Michigan/Skyline Fireworks Party Cruise

Our flagship vessel boasts a Tiki Chic vibe, two climate controlled decks, two bars, two bathrooms, premium sound system, outdoor and indoor viewing areas.

  • Instant confirmation
  • Short pick · ≤2h
From $53 a person
This tour cruises the Chicago River and Lake Michigan.
1h 30m

Chicago Lake and River Architecture Tour

An authentic Chicago tradition since 1935, this is the tour that started it all.

  • 4.7★ · 2360 reviews
  • Bestseller
From $45 a person
Kid smiling faces say it all on our Family Friendly Chicago Food & Bike Tour. Ride a Bicycle, taste local favorites, and enjoy one of the best Kid-Friendly Things to do in Chicago.
4h

Chicago Family Food and Bike Tour with Top Attractions

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in America by USA Today...

  • 4.8★ · 99 reviews
  • Free cancellation
From $79 a person
5h 30m

Kyoto Arashiyama: Fall Foliage Walking Tour【Autumn's limited】

Experience the unique charm of Arashiyama in autumn with our exclusive private tour, available only during this brief but breathtaking season.

  • Free cancellation
  • Instant confirmation
From $111 a person
The Chicago Loop is the city's epicenter of culture, commerce, and design.
2h to 2h 30m

Self-Guided Chicago Loop Tour Explore the City at Your Own Pace

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown.

  • Free cancellation
  • Instant confirmation
From $10 a person
24h

Milwaukee Day Tour from Chicago w/Optional Foliage Season Upgrade

（For Non-foliage season tour）Visit Milwaukee’s top attractions: Harley-Davidson Museum, Public Market, Miller Brewery & Milwaukee Art Museum Seasonal upgrade available during...

  • Free cancellation
  • Likely to sell out
From $125 a person
1h 30m

Wind and Souls an Adults Only Ghost Tour in Chicago

Leave the little ones at home and step into the shadows for a spine-chilling evening designed exclusively for adults.

  • Free cancellation
  • Instant confirmation
From $35 a person
3h 30m

NYC Fall Foliage Cruise: Experience Autumn's Beauty

Embark on a 3.5-hour cruise that transforms New York City into an autumn masterpiece.

  • Free cancellation
  • Instant confirmation
From $59 a person
2h 30m

New York Fall Foliage Cruise up the Hudson River

Enjoy a fall foliage cruise aboard Yacht Kingston, a cozy, elegant, 1920s-style yacht with an observation cabin and open bow.

  • Free cancellation
  • Instant confirmation
From $111 a person
1h to 1h 15m

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

Explore haunted Chicago at your own pace and schedule.

  • Free cancellation
  • Instant confirmation
From $10 a person
1h 30m

Chicago Fireboat Fireworks Cruise

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise.

  • Free cancellation
  • Instant confirmation
From $57 a person
30 min

Flyover in Chicago

The Flyover experience takes 30 minutes from beginning to end.

  • Top-rated · 4.7★
  • Free cancellation
From $28 a person
Skyline Queen showcasing the Chicago Skyline!
1h 30m

Chicago Sightseeing River and Lake Cruise

Our popular 90-minute daytime river and lake sightseeing tour delights family members of all ages with incredible views of Chicago's world-renowned buildings and stunning skyline.

  • Top-rated · 4.7★
  • Free cancellation
From $46 a person
1h 30m

Lake Michigan Sunset Cruise in Chicago

The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats.

  • 4.5★ · 1609 reviews
  • Bestseller
From $45 a person
Chicago Food Tour
2h

Chicago Loop Food Tour: Taste the Most Iconic Local Eats

Join a local guide for the ultimate foodie adventure in Chicago’s historic Loop, tasting classics like deep‑dish pizza and Chicago‑style hot dogs while discovering insider stories...

  • Top-rated · 4.8★
  • Free cancellation
From $87 a person
A picture of Chicago Chinatown’s landscape shows vibrant streets, iconic arches, and rich culture—everything guests explore on our Chinatown Food Tours. Food Tours in Chinatown bring it all to life.
3h

Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history.

  • Top-rated · 4.9★
  • Free cancellation
From $80 a person
2h 15m

Lincoln Park Hauntings Ghost Investigation Tour

We are Chicago's only paranormal investigation tour, and Chicago's oldest ghost and hauntings tours, founded by Ursula Bielski, Chicago's 35 year paranormal researcher and...

  • Free cancellation
  • Instant confirmation
From $40 a person
Feel the presence of the unseen as we wander through haunted history under the moon's glow.
1h

Embers of the Windy City: Chilling Chicago Ghost Tours

Come on our chilling ghost tour presented by US Ghost Adventures!

  • Free cancellation
  • Short pick · ≤2h
From $26 a person
From deep-dish to hot dogs, taste Chicago Classic Dishes on our Chicago Food & Bike Tour. Ride by Bicycle, learn the stories, and savor every stop on the best Food & Bike Tour in Chicago.
4h 30m

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour!

  • Top-rated · 5.0★
  • Free cancellation
From $89 a person
See Chicago's magnificent skyline at night!
1h 30m

Chicago By Night River and Lake Cruise

Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night!

  • Free cancellation
  • Instant confirmation
From $50 a person
216h

Chicago CityPASS®

Experience 5 top attractions and save up to 50% with Chicago CityPASS® tickets.

  • Instant confirmation
From $144 a person
3h

Skyline, Lakefront and Millennium Park Chicago Private Day Tour

Explore Chicago’s iconic landmarks and scenic lakefront on a private, fully personalized city tour.

  • Free cancellation
  • Instant confirmation
From $168 a person
4h

Fall Foliage Oktoberfest Cruise on the Hudson River

Set sail on a festive autumn adventure with the Fall Foliage Oktoberfest Cruise, running from October 4 to November 7.

  • Free cancellation
  • Instant confirmation
From $99 a person
3h

Chicago Cubs Baseball Game at Wrigley Field

One of the oldest and most iconic franchises in Major League Baseball and a founding member of the National League, the Chicago Cubs’ legacy dates all the way back to 1876.

  • Instant confirmation
  • Half-day
From $69 a person

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