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LGBT Friendly Tours LGBT Friendly Tours Kid-Friendly Kid-Friendly Excellent Quality Excellent Quality Wayfortravel Plus Wayfortravel Plus Sporting Event Tickets & Passes Sporting Event Tickets & Passes Best Conversion Best Conversion Involves Animals Involves Animals Good for avoiding crowds Good for avoiding crowds Seasonal & Special Occasions Seasonal & Special Occasions Classes & Workshops Classes & Workshops Travel & Transportation Services Travel & Transportation Services Tours, Sightseeing & Cruises Tours, Sightseeing & Cruises Tickets & Passes Tickets & Passes Food & Drink Food & Drink Art & Culture Art & Culture Outdoor Activities Outdoor Activities Small Group Small Group Likely to Sell Out Likely to Sell Out Audio Guides Audio Guides Sustainable Tours Sustainable Tours Limousine Transfers Limousine Transfers Donut Walking Tour Donut Walking Tour Virtual Experiences Virtual Experiences Additional fees Additional fees DSA non-compliant DSA non-compliant Low Last Minute Supplier Cancellation Rate Low Last Minute Supplier Cancellation Rate
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LGBT Friendly Tours LGBT Friendly Tours Kid-Friendly Kid-Friendly Excellent Quality Excellent Quality Wayfortravel Plus Wayfortravel Plus Sporting Event Tickets & Passes Sporting Event Tickets & Passes Best Conversion Best Conversion Involves Animals Involves Animals Good for avoiding crowds Good for avoiding crowds Seasonal & Special Occasions Seasonal & Special Occasions Classes & Workshops Classes & Workshops Travel & Transportation Services Travel & Transportation Services Tours, Sightseeing & Cruises Tours, Sightseeing & Cruises Tickets & Passes Tickets & Passes Food & Drink Food & Drink Art & Culture Art & Culture Outdoor Activities Outdoor Activities Small Group Small Group Likely to Sell Out Likely to Sell Out Audio Guides Audio Guides Sustainable Tours Sustainable Tours Limousine Transfers Limousine Transfers Donut Walking Tour Donut Walking Tour Virtual Experiences Virtual Experiences Additional fees Additional fees DSA non-compliant DSA non-compliant Low Last Minute Supplier Cancellation Rate Low Last Minute Supplier Cancellation Rate

Seasonal & Special Occasions in Chicago

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Chicago to Milwaukee:Day Trip with Brewery Tour & City Highlights
Chicago to Milwaukee:Day Trip with Brewery Tour & City Highlights
Starting at
$125.00
4/5
Overview
Welcome to the amazing city of Chicago.Discover the mechanics behind how motorcycles work and learn about the iconic history of Harley-Davidson through a gallery of bikes from 1903 to the present. Vis...
1 reviews
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Chicago Private Boat Rental - Explore Chicago's Skyline & Waters
Chicago Private Boat Rental - Explore Chicago's Skyline & Waters
Starting at
$2275.00
5/5
Overview
Our Mission: We are dedicated to curating exceptional boating experiences, offering day and night cruises, fireworks displays, and serene voyages along the Chicago River. Our goal is to share the magi...
1 reviews
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Chicago River Sunday Funday Mimosa or Bloody Mary Party Cruise
Chicago River Sunday Funday Mimosa or Bloody Mary Party Cruise
Starting at
$35.00
4/5
Overview
Sunday Funday Mimosa Cruise – Chicago’s Floating Tiki Bar Adventure! Sundays are Fun-Days aboard our vibrant floating tiki bar, Island TIme, where the drinks are cold, the vibes are high, and the...
1 reviews
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Chicago Skyline Tiki Chic Party Cruise on Lake Michigan
Chicago Skyline Tiki Chic Party Cruise on Lake Michigan
Starting at
$35.00
4/5
Overview
Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. Your adventure begins on the iconic Chicago Riverwalk, where you’ll board a beautifully appointed boat featuring...
1 reviews
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Peep Show Ticket in Chicago
Peep Show Ticket in Chicago
Starting at
$40.00
5/5
Overview
Peep Show is Chicago's finest burlesque and comedy revue! In 90 minutes, each show features a rotating cast of up to 4 dancers, performing original striptease dances for our audiences! We also add hil...
1 reviews
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Experience Chicago Cooking Class with Deep Dish Pizza or Pasta
Experience Chicago Cooking Class with Deep Dish Pizza or Pasta
Starting at
$109.00
5/5
Overview
This experience combines Chicago's iconic deep-dish pizza or Italian-American pasta with a warm, hands-on cooking class led by Nancy and her daughter Hailey. Enjoy personalized guidance, homemade reci...
1 reviews
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Party Boat Services in Chicago
Party Boat Services in Chicago
Starting at
$1400.00
5/5
Overview
Experience the beauty and excitement of Chicago from the water aboard Misunderstood, a premier charter boat perfect for parties, events, or a relaxing day on Lake Michigan. Cruise past iconic landmark...
1 reviews
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Chicago New Year's Eve Buffet Dinner Cruise on Lake Michigan
Chicago New Year's Eve Buffet Dinner Cruise on Lake Michigan
Starting at
$273.26
4/5
Overview
Embark on the ultimate New Year’s Eve celebration with our Signature Dinner Fireworks Dinner Cruise. Come together for unparalleled festivities with dining, dancing, and magnificent skyline views li...
1 reviews
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Chicago River Spectacular Fireworks Show and Tiki Bar Cruise
Chicago River Spectacular Fireworks Show and Tiki Bar Cruise
Starting at
$40.00
4/5
Overview
Fireworks Cruise Aboard Island Time – See the Sparks Fly the Island Party Way! Experience Chicago’s dazzling fireworks like never before—from the deck of our floating Tiki Bar, Island Time! Cru...
1 reviews
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New Year's Eve Plated Dinner Cruise on Lake Michigan
New Year's Eve Plated Dinner Cruise on Lake Michigan
Starting at
$341.59
5/5
Overview
Set sail on a breathtaking celebration with a Premier Chicago New Year’s Eve Fireworks Dinner Cruise on Lake Michigan. Indulge in an unforgettable evening of delicious craft cocktails, plated, chef-...
1 reviews
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Drunk Shakespeare Ticket – Chicago
Drunk Shakespeare Ticket – Chicago
Starting at
$29.00
5/5
Overview
One actor has five shots of whiskey and then attempts to perform in a Shakespeare play. New York Times Critics' Pick!...
1 reviews
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Chicago Skyline Sunday Funday Mimosa/Bloody Mary Party Cruise
Chicago Skyline Sunday Funday Mimosa/Bloody Mary Party Cruise
Starting at
$40.00
4/5
Overview
Kick off your Sunday the right way—with mimosas, Bloody Marys , and unbeatable views of Chicago’s stunning skyline aboard Enchantment, our flagship vessel. This ticketed cruise is the perfect blen...
1 reviews
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Chicago to Washington D.C. Cherry Blossom 3-Day Tour
Chicago to Washington D.C. Cherry Blossom 3-Day Tour
Starting at
$476.00
5/5
Overview
Celebrate the beauty of spring and the rich history of the National Cherry Blossom Festival, commemorating the 1912 gift of 3,000 cherry trees from Tokyo to Washington, D.C. Visit iconic landmarks lik...
1 reviews
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Fright Hike: Chicago Halloween Bike Tour
Fright Hike: Chicago Halloween Bike Tour
Starting at
$54.99
5/5
Overview
Come get spooked on Bobby’s Fright Hike! Bobby’s Bike Hike is America’s longest running city bicycle company, and this is Chicago’s premiere Halloween ghost tour. Hop on two wheels and follow ...
1 reviews
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Chicago Local Brewery Expedition with Homemade Guacamole
Chicago Local Brewery Expedition with Homemade Guacamole
Starting at
$54.00
5/5
Overview
We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; which used to be the meatpacking district,...
1 reviews
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Chicago’s Festive Lights: A Magical Christmas Journey
Chicago’s Festive Lights: A Magical Christmas Journey
Starting at
$370.87
5/5
Overview
“Chicago’s Festive Lights: A Magical Christmas Journey” takes you through the heart of the Windy City during the most wonderful time of the year. Begin your tour at 875 North Michigan Avenue, fo...
1 reviews
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