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Top 10 Best Chicago Unique Experiences

Found 476 Unique Experiences activities in Chicago. Sort by Popularity. - Page 7
 

Burlesque Peep Show Ticket in Chicago

(4.8 of 9 reviews)

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 hilarious comedians, mystifying m... More

Free Cancellation
Start From $25.00
 
Burlesque Peep Show Ticket in Chicago

Burlesque Peep Show Ticket in Chicago

  • Chicago
  • Superb9 reviews4.8

Peep Show is Chicago's finest burlesque and comedy revue! In 90 minutes, each show features a rotati....

    Free Cancellation
    Start From $25.00
 
 

Chicago Riverwalk Self-Guided Walking Tour

(4.2 of 6 reviews)

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city second Lakefront', the Riverwalk contains restaurants during the summer months, seating areas to relax, boat rentals, an... More

Free Cancellation
Private Tour
Start From $14.99
 
Chicago Riverwalk Self-Guided Walking Tour

Chicago Riverwalk Self-Guided Walking Tour

  • Chicago
  • Exellent6 reviews4.2

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called....

    Free Cancellation
    Private Tour
    Start From $14.99
 
 

360 Chicago Observation Deck Sip and View Ticket

(4.1 of 81 reviews)

The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City in the former John Hancock Building, 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering s... More

Free Cancellation
Private Tour
Start From $44.00
 
360 Chicago Observation Deck Sip and View Ticket

360 Chicago Observation Deck Sip and View Ticket

  • Chicago
  • Exellent81 reviews4.1

The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the....

    Free Cancellation
    Private Tour
    Start From $44.00
 
 

Chicago Craft Brewery Barrel Bus Tour

(4.9 of 331 reviews)

There’s never been a better time to be a beer drinker — and Chicago, with its thriving brewery scene and many destination-worthy beer bars, is the perfect city for suds lovers. Visit three of its craft breweries on this all-in... More

Free Cancellation
Private Tour
Start From $99.60
 
Chicago Craft Brewery Barrel Bus Tour Likely to Sell Out

Chicago Craft Brewery Barrel Bus Tour

  • Chicago
  • Superb331 reviews4.9

There’s never been a better time to be a beer drinker — and Chicago, with its thriving brewery s....

    Free Cancellation
    Private Tour
    Start From $99.60
 
 

Chicago Mobs and Haunts Walking Tour

(4.7 of 375 reviews)

Join us along the historic streets and alleys of Chicago as we walk among the spirits of mobsters and ghosts of the condemned. This tour is for lovers of history, true crime, and haunted mysteries. Expect a sultry and gritty cock... More

Free Cancellation
Private Tour
Start From $34.00
 
Chicago Mobs and Haunts Walking Tour Likely to Sell Out

Chicago Mobs and Haunts Walking Tour

  • Chicago
  • Superb375 reviews4.7

Join us along the historic streets and alleys of Chicago as we walk among the spirits of mobsters an....

    Free Cancellation
    Private Tour
    Start From $34.00
 
 

Chicago Helicopter 10-Minute Tour for up to Three Passengers

(4.3 of 31 reviews)

A helicopter tour of downtown Chicago is a unique and thrilling way to experience the Windy City. From high up in the sky, you'll be able to take in breathtaking panoramic views of Chicago's iconic skyline, world-famous landmarks,... More

Free Cancellation
Private Tour
Start From $375.00
 
Chicago Helicopter 10-Minute Tour for up to Three Passengers Likely to Sell Out

Chicago Helicopter 10-Minute Tour for up to Three Passengers

  • Chicago
  • Exellent31 reviews4.3

A helicopter tour of downtown Chicago is a unique and thrilling way to experience the Windy City. Fr....

    Free Cancellation
    Private Tour
    Start From $375.00
 
 

Chicago Gangsters and Movies Tour

(5 of 27 reviews)

Mobsters and Movies takes you through the real haunts of Capone, Dillinger, and The Outfit—then shows you how the very same streets turned into movie magic. Walk the same corners seen in 'The Untouchables' and 'Public Enemies,' ... More

Free Cancellation
Private Tour
Start From $35.00
 
Chicago Gangsters and Movies Tour Likely to Sell Out

Chicago Gangsters and Movies Tour

  • Chicago
  • Superb27 reviews5

Mobsters and Movies takes you through the real haunts of Capone, Dillinger, and The Outfit—then sh....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 

Skydeck Chicago: Pie in the Sky VIP Dinner at Willis Tower

(3.6 of 42 reviews)

Indulge in a VIP dinner experience at Chicago’s Skydeck, offering breathtaking views from 1,353 feet (412 meters) above the city. Located in the iconic Willis Tower, this exclusive experience lets you enjoy the stunning skyline ... More

Free Cancellation
Private Tour
Start From $154.00
 
Skydeck Chicago: Pie in the Sky VIP Dinner at Willis Tower Likely to Sell Out

Skydeck Chicago: Pie in the Sky VIP Dinner at Willis Tower

  • Chicago
  • Very Good42 reviews3.6

Indulge in a VIP dinner experience at Chicago’s Skydeck, offering breathtaking views from 1,353 fe....

    Free Cancellation
    Private Tour
    Start From $154.00
 
 

Private 45-Minute Chicago Skyline Helicopter Tour

(4.8 of 126 reviews)

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the city of Chicago on a 45 minute thrill seeking guided tour. The price is... More

Free Cancellation
Private Tour
Start From $849.00
 
Private 45-Minute Chicago Skyline Helicopter Tour Likely to Sell Out

Private 45-Minute Chicago Skyline Helicopter Tour

  • Chicago
  • Superb126 reviews4.8

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3....

    Free Cancellation
    Private Tour
    Start From $849.00
 
 

Delicious Donuts & City Sights: Chicago's Original Donut Tour

(4.9 of 1,377 reviews)

Recently voted one of TripAdvisor's top food tours in the US. Discover the sweet side of the Windy City on the Underground Donut Tour, Chicago’s Delicious Donut Adventure. We’ll kick things off at the legendary Doughnut Vaul... More

Free Cancellation
Private Tour
Start From $70.00
 
Delicious Donuts & City Sights: Chicago's Original Donut Tour Likely to Sell Out

Delicious Donuts & City Sights: Chicago's Original Donut Tour

  • Chicago
  • Superb1,377 reviews4.9

Recently voted one of TripAdvisor's top food tours in the US. Discover the sweet side of the Windy....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Chicago Lincoln Park Indoor Skydiving with Two Flights

(4.6 of 67 reviews)

When you arrive at the Chicago Lincoln Park indoor skydiving location, get started by putting on your provided gear and going through a specialized training session from a flight instructor. Learn how to safely float in a 1,400-h... More

Free Cancellation
Private Tour
Start From $102.46
 
Chicago Lincoln Park Indoor Skydiving with Two Flights Likely to Sell Out

Chicago Lincoln Park Indoor Skydiving with Two Flights

  • Chicago
  • Superb67 reviews4.6

When you arrive at the Chicago Lincoln Park indoor skydiving location, get started by putting on you....

    Free Cancellation
    Private Tour
    Start From $102.46
 
 

Luxury Minibus Chicago City Tour

(4.7 of 3 reviews)

Experience Chicago in Style with Our Luxury City Sightseeing Minibus Tour. Indulge in the ultimate Chicago adventure on our top-rated, luxury sightseeing minibus tour. This 2-hour, expertly guided experience takes you through the ... More

Free Cancellation
Private Tour
Start From $65.00
 
Luxury Minibus Chicago City Tour Likely to Sell Out

Luxury Minibus Chicago City Tour

  • Chicago
  • Superb3 reviews4.7

Experience Chicago in Style with Our Luxury City Sightseeing Minibus Tour. Indulge in the ultimate C....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

(5 of 27 reviews)

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Free Cancellation
Private Tour
Start From $507.96
 
Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago Likely to Sell Out

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

  • Chicago
  • Superb27 reviews5

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....

    Free Cancellation
    Private Tour
    Start From $507.96
 
 

Verse Immersive Holographic Theater in Chicago

(5 of 14 reviews)

HIGHLIGHTS - The World's First Holographic Theater - Wield real magic, stroll through the cosmos, or train and battle life-sized dinosaurs – Verse has it all - Great for Families, Date Nights, and Solo Adventures Step into a li... More

Free Cancellation
Private Tour
Start From $39.99
 
Verse Immersive Holographic Theater in Chicago Likely to Sell Out

Verse Immersive Holographic Theater in Chicago

  • Chicago
  • Superb14 reviews5

HIGHLIGHTS - The World's First Holographic Theater - Wield real magic, stroll through the cosmos, or....

    Free Cancellation
    Private Tour
    Start From $39.99
 
 

Chicago Night Driving Tour with Skydeck and River Cruise

(4.3 of 26 reviews)

Discover Chicago’s most iconic landmarks illuminated after dark on this small-group night tour (max 6 guests) with hotel pick-up and drop-off included in the price. Start your evening at the legendary Willis Tower Skydeck, the... More

Free Cancellation
Private Tour
Start From $189.00
 
Chicago Night Driving Tour with Skydeck and River Cruise Likely to Sell Out

Chicago Night Driving Tour with Skydeck and River Cruise

  • Chicago
  • Exellent26 reviews4.3

Discover Chicago’s most iconic landmarks illuminated after dark on this small-group night tour (ma....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Drunk Shakespeare Ticket – Chicago

(4.6 of 154 reviews)

One actor has five shots of whiskey and then attempts to perform in a Shakespeare play. New York Times Critics' Pick!... More

Free Cancellation
Private Tour
Start From $29.00
 
Drunk Shakespeare Ticket – Chicago Likely to Sell Out

Drunk Shakespeare Ticket – Chicago

  • Chicago
  • Superb154 reviews4.6

One actor has five shots of whiskey and then attempts to perform in a Shakespeare play. New York Tim....

    Free Cancellation
    Private Tour
    Start From $29.00
 
 

Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max

(5 of 143 reviews)

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour semi-private (12 Guest Maximum) guided museum tour, you’ll be able to skip the line... More

Free Cancellation
Private Tour
Start From $90.01
 
Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max Likely to Sell Out

Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max

  • Chicago
  • Superb143 reviews5

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Me....

    Free Cancellation
    Private Tour
    Start From $90.01
 
 

Chicago Scavenger Hunt Adventure

(5 of 5 reviews)

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-bas... More

Free Cancellation
Private Tour
Start From $29.00
 
Chicago Scavenger Hunt Adventure Likely to Sell Out

Chicago Scavenger Hunt Adventure

  • Chicago
  • Superb5 reviews5

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, p....

    Free Cancellation
    Private Tour
    Start From $29.00
 
 

Private Acrylic Painting Class in Chicago

(5 of 5 reviews)

Our "Fluid Art" experience is truly unique. It offers a mesmerizing journey into the world of art unlike any other. Participants are guided through an exciting process using acrylic paints, silicone, a hair dryer, and a gas burner... More

Free Cancellation
Private Tour
Start From $88.00
 
Private Acrylic Painting Class in Chicago Likely to Sell Out

Private Acrylic Painting Class in Chicago

  • Chicago
  • Superb5 reviews5

Our "Fluid Art" experience is truly unique. It offers a mesmerizing journey into the world of art un....

    Free Cancellation
    Private Tour
    Start From $88.00
 
 

Private Transfer Chicago Airport to Chicago by Luxury Car or SUV

(5 of 1 review)

Why spend your precious time waiting in long shuttle or taxi lines? Avoid the language barrier and currency exchange. Travel in style from Chicago O'Hare Airport ORD or Chicago Midway Airport to your Hotel in Chicago by priva... More

Free Cancellation
Private Tour
Start From $115.26
 
Private Transfer Chicago Airport to Chicago by Luxury Car or SUV Likely to Sell Out

Private Transfer Chicago Airport to Chicago by Luxury Car or SUV

  • Chicago
  • Superb1 review5

Why spend your precious time waiting in long shuttle or taxi lines? Avoid the language barrier and c....

    Free Cancellation
    Private Tour
    Start From $115.26
 
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