Menu

Top 10 Best Chicago Unique Experiences

Found 441 Unique Experiences activities in Chicago. Sort by Popularity. - Page 17
 

Private Transfer from Chicago City to Chicago (ORD) Airport

(5 of 1 review)

Take the worry out of your departure to Chicago Airport and pre-book a private transfer to suit your group size (up to 14 people). Avoid the long lines for taxis at the hotel, and travel in the comfort of a Premium car or minivan.... More

Free Cancellation
Private Tour
Start From $297.26
 
Private Transfer from Chicago City to Chicago (ORD) Airport

Private Transfer from Chicago City to Chicago (ORD) Airport

  • Chicago
  • Superb1 review5

Take the worry out of your departure to Chicago Airport and pre-book a private transfer to suit your....

    Free Cancellation
    Private Tour
    Start From $297.26
 
 

A Storied Neighborhood: A Self-Guided Audio Tour with Bill Ayers

(3.5 of 2 reviews)

This self-guided audio tour begins at the Laboratory Schools founded by John Dewey, and winds through the University of Chicago. Along the way, walkers will encounter world-renowned architects and Nobel Laureates, robber barons an... More

Free Cancellation
Private Tour
Start From $5.40
 
A Storied Neighborhood: A Self-Guided Audio Tour with Bill Ayers

A Storied Neighborhood: A Self-Guided Audio Tour with Bill Ayers

  • Chicago
  • Good2 reviews3.5

This self-guided audio tour begins at the Laboratory Schools founded by John Dewey, and winds throug....

    Free Cancellation
    Private Tour
    Start From $5.40
 
 

2 Hour Magnificent Chicago Tour with Photos and Popcorn

(5 of 1 review)

Be welcomed and greeted in Chicago from a TRUE native of the city. Experience the vibrant history and culture of the city while being professional photographed, and enjoying Chicago's famous Garrett's popcorn. This tour is lead by... More

Free Cancellation
Private Tour
Start From $35.00
 
2 Hour Magnificent Chicago Tour with Photos and Popcorn

2 Hour Magnificent Chicago Tour with Photos and Popcorn

  • Chicago
  • Superb1 review5

Be welcomed and greeted in Chicago from a TRUE native of the city. Experience the vibrant history an....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 
-20% Gangs and Mobsters Crime Tour at Chicago

Gangs and Mobsters Crime Tour at Chicago

(5 of 1 review)

Embark on a captivating walking tour that delves into the intriguing legacy of the Midwest's most notorious mobsters and gangs. Immerse yourself in the rich history of the Windy City as you stroll through its vibrant streets, wher... More

Special Offer
Free Cancellation
Private Tour
Start From $26.40
(Saving 20% ) $33.00
 
-20% Gangs and Mobsters Crime Tour at Chicago

Gangs and Mobsters Crime Tour at Chicago

  • Chicago
  • Superb1 review5

Embark on a captivating walking tour that delves into the intriguing legacy of the Midwest's most no....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $26.40
    (Saving 20% ) $33.00
 
 

Fun City Scavenger Hunt in Chicago by 3Quest Challenge

(5 of 1 review)

The Chicago 3Quest Challenge is a scavenger hunt done on an app where players will find objects (given in the form of riddles) and complete fun challenges for points. The items & challenges are separated into 3 quests. Complete qu... More

Free Cancellation
Private Tour
Start From $10.00
 
Fun City Scavenger Hunt in Chicago by 3Quest Challenge

Fun City Scavenger Hunt in Chicago by 3Quest Challenge

  • Chicago
  • Superb1 review5

The Chicago 3Quest Challenge is a scavenger hunt done on an app where players will find objects (giv....

    Free Cancellation
    Private Tour
    Start From $10.00
 
 

Private Transfer from Chicago City to Chicago Airport (ORD)

(5 of 1 review)

Book a private transfer from your hotel or destination to Airport, service guaranteed once you make the booking. We will provide all information necessary to meet your driver at hotel or destination. • Meet and greet • Priv... More

Free Cancellation
Private Tour
Start From $61.25
 
Private Transfer from Chicago City to Chicago Airport (ORD)

Private Transfer from Chicago City to Chicago Airport (ORD)

  • Chicago
  • Superb1 review5

Book a private transfer from your hotel or destination to Airport, service guaranteed once you make ....

    Free Cancellation
    Private Tour
    Start From $61.25
 
 

Chicago Scav Hunt

(5 of 1 review)

Take your shot at completing this Chicago Scavenger Hunt around the Loop and River North neighborhoods including the Riverwalk. Complete this solo or build a ScavSquad of up to 5 people and discover the city like never before! Use... More

Free Cancellation
Private Tour
Start From $8.00
 
Chicago Scav Hunt

Chicago Scav Hunt

  • Chicago
  • Superb1 review5

Take your shot at completing this Chicago Scavenger Hunt around the Loop and River North neighborhoo....

    Free Cancellation
    Private Tour
    Start From $8.00
 
 

Social Justice and Art History Walking Tour in Southside Chicago

(5 of 1 review)

Embark on a transformative tour of Chicago's Southside, delving into its vibrant street art scene and rich history of social justice activism. Explore captivating murals infused with artivism, and hear stories of iconic figures in... More

Free Cancellation
Private Tour
Start From $45.00
 
Social Justice and Art History Walking Tour in Southside Chicago

Social Justice and Art History Walking Tour in Southside Chicago

  • Chicago
  • Superb1 review5

Embark on a transformative tour of Chicago's Southside, delving into its vibrant street art scene an....

    Free Cancellation
    Private Tour
    Start From $45.00
 
 

Scavenger Hunt in Chicago by Wacky Walks

(5 of 1 review)

Starting near Vietnam Veterans Memorial in Chicago, complete Wacky Walks by using an app to find a list of objects around the city and participate in fun challenges for points. Collect points and take a look at your score compared... More

Free Cancellation
Private Tour
Start From $10.00
 
Scavenger Hunt in Chicago by Wacky Walks

Scavenger Hunt in Chicago by Wacky Walks

  • Chicago
  • Superb1 review5

Starting near Vietnam Veterans Memorial in Chicago, complete Wacky Walks by using an app to find a l....

    Free Cancellation
    Private Tour
    Start From $10.00
 
 

Self-Guided Chicago Scavenger Hunt: Chicago Loop

(5 of 1 review)

Let’s Roam is the top app-led adventure hunt company! Explore all the best landmarks and hidden gems, answering trivia questions and tackling exciting challenges along the way. Team up with your friends or compete against them a... More

Free Cancellation
Private Tour
Start From $13.08
 
Self-Guided Chicago Scavenger Hunt: Chicago Loop

Self-Guided Chicago Scavenger Hunt: Chicago Loop

  • Chicago
  • Superb1 review5

Let’s Roam is the top app-led adventure hunt company! Explore all the best landmarks and hidden ge....

    Free Cancellation
    Private Tour
    Start From $13.08
 
 

Explore the Historic Old Post Office in Chicago

(5 of 2 reviews)

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once seemed as though the stunning architectural details of Chicago's Old P... More

Free Cancellation
Private Tour
Start From $15.00
 
Explore the Historic Old Post Office in Chicago Likely to Sell Out

Explore the Historic Old Post Office in Chicago

  • Chicago
  • Superb2 reviews5

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused....

    Free Cancellation
    Private Tour
    Start From $15.00
 
 

Chicago Midway Airport (MDW) to Chicago City - Round-Trip Private Transfer

(5 of 2 reviews)

Book your Private Round-Trip Transfer from Chicago Midway Airport (MDW) to Chicago or address and return. Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door to door airpo... More

Free Cancellation
Private Tour
Start From $101.92
 
Chicago Midway Airport (MDW) to Chicago City - Round-Trip Private Transfer Likely to Sell Out

Chicago Midway Airport (MDW) to Chicago City - Round-Trip Private....

  • Chicago
  • Superb2 reviews5

Book your Private Round-Trip Transfer from Chicago Midway Airport (MDW) to Chicago or address and re....

    Free Cancellation
    Private Tour
    Start From $101.92
 
 

Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

(5 of 2 reviews)

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the footsteps of the gangsters, bootleggers, hoodlums, gunmen, and crooked cops and politicians w... More

Free Cancellation
Private Tour
Start From $6.99
 
Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour Likely to Sell Out

Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

  • Chicago
  • Superb2 reviews5

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affor....

    Free Cancellation
    Private Tour
    Start From $6.99
 
 

Private Transfer from Chicago (MDW) Airport to Chicago City

(5 of 2 reviews)

Take the worry out of your arrival to Chicago (MDW) Airport and pre-book a private transfer to suit your group size (up to 14 people). Avoid the long lines for taxis on arrival, and travel in the comfort of a Premium car or miniva... More

Free Cancellation
Private Tour
Start From $140.14
 
Private Transfer from Chicago (MDW) Airport to Chicago City Likely to Sell Out

Private Transfer from Chicago (MDW) Airport to Chicago City

  • Chicago
  • Superb2 reviews5

Take the worry out of your arrival to Chicago (MDW) Airport and pre-book a private transfer to suit ....

    Free Cancellation
    Private Tour
    Start From $140.14
 
 

Chicago Architecture, Art and History Tour - Off The Beaten Path

(5 of 2 reviews)

This short but sweet and unique adventure will take you on a 2-hour walking tour by the interiors of the most iconic buildings of Chicago downtown. Dive into the extravaganza of splendid hidden gems of the city as you explore the... More

Free Cancellation
Private Tour
Start From $95.00
 
Chicago Architecture, Art and History Tour - Off The Beaten Path Likely to Sell Out

Chicago Architecture, Art and History Tour - Off The Beaten Path

  • Chicago
  • Superb2 reviews5

This short but sweet and unique adventure will take you on a 2-hour walking tour by the interiors of....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

1 Hour Photoshoot in Chicago

(5 of 2 reviews)

In this photoshoot you will have most iconic and important places in downtown Chicago, places where you need to have a photo with , and in a unique way with your own personal photographer. We will have the most photogenic and beau... More

Free Cancellation
Private Tour
Start From $179.00
 
1 Hour Photoshoot in Chicago Likely to Sell Out

1 Hour Photoshoot in Chicago

  • Chicago
  • Superb2 reviews5

In this photoshoot you will have most iconic and important places in downtown Chicago, places where ....

    Free Cancellation
    Private Tour
    Start From $179.00
 
 

Chicago Haunts and Hooligans Tour

(5 of 16 reviews)

Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a recent transplant to Chicag... More

Free Cancellation
Private Tour
Start From $34.77
 
Chicago Haunts and Hooligans Tour Likely to Sell Out

Chicago Haunts and Hooligans Tour

  • Chicago
  • Superb16 reviews5

Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret p....

    Free Cancellation
    Private Tour
    Start From $34.77
 
 

Walking tour to Chicago dive bars

(5 of 2 reviews)

The only walking tour that takes you to real neighborhood taverns, pubs, and dive bars in Chicago. The tour covers about a mile in the West Loop neighborhood. You won't find tourists here. You won't find famous sports figures. You... More

Free Cancellation
Private Tour
Start From $41.03
 
Walking tour to Chicago dive bars Likely to Sell Out

Walking tour to Chicago dive bars

  • Chicago
  • Superb2 reviews5

The only walking tour that takes you to real neighborhood taverns, pubs, and dive bars in Chicago. T....

    Free Cancellation
    Private Tour
    Start From $41.03
 
 

4 Hours of Chicago City Tour Sedan

(5 of 2 reviews)

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city... More

Free Cancellation
Private Tour
Start From $640.00
 
4 Hours of Chicago City Tour Sedan Likely to Sell Out

4 Hours of Chicago City Tour Sedan

  • Chicago
  • Superb2 reviews5

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating....

    Free Cancellation
    Private Tour
    Start From $640.00
 
 

Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

(5 of 1 review)

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding a bike. Dive into the atmosphere of the city’s movement and c... More

Free Cancellation
Private Tour
Start From $179.00
 
Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer Likely to Sell Out

Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

  • Chicago
  • Superb1 review5

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a frien....

    Free Cancellation
    Private Tour
    Start From $179.00
 
Booking.com
Booking.com
Booking.com