Illinois Luxury Tours

Historic Homes and Cottages of Wicker Park Walking Tour

Much of the historical information shared on this tour is unknown to most attendees. This tour also shows everything from the gritty to the pretty, …More

Chicago, USA

Much of the historical information shared on this tour is unknown to most attendees. This tour also shows everything from the gritty to the pretty,...

1 hour 30 minutes
5.0 (53)
from
$45
Chicago-Style Holiday Hike: Festive Food and Walking Tour

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holiday Hike, a 3-hour guided …More

Chicago, USA

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holiday Hike, a 3-hour guided...

3 hours Free Cancellation
5.0 (77)
from
$85
Chicago Loop Walking Tour

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists. …More

Chicago, USA

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists....

2 hours Free Cancellation
4.9 (56)
from
$60
The Deep Pockets Of Graceland Cemetery Walking Tour

Dive into this captivating journey through the hallowed grounds of Chicago’s Graceland Cemetery. As we stroll amidst the stunning and serene beauty of historic resting …More

Chicago, USA

Dive into this captivating journey through the hallowed grounds of Chicago’s Graceland Cemetery. As we stroll amidst the stunning and serene beauty of historic resting...

1 hour 30 minutes Free Cancellation
4.9 (13)
from
$45
Chicago Full-Day Walking Food Tour with Free Bike or Kayak Rental

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary...

5 hours Free Cancellation
5.0 (3)
from
$99
Frank Lloyd Wright Oak Park Architecture Tour from Chicago

Explore the architectural genius of Frank Lloyd Wright on a private, fully personalized tour in Chicago, home to the world’s largest collection of his buildings. …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA

Explore the architectural genius of Frank Lloyd Wright on a private, fully personalized tour in Chicago, home to the world’s largest collection of his buildings....

5 hours Hotel pickup offered Free Cancellation
4.4 (10)
from
$78
Chicago River Floating Tiki Bar Cruise Friday and Saturday

Set sail for an unforgettable evening aboard the River Star or Island Time, where the drinks are flowing and the views are unmatched. Enjoy a …More

Chicago, USA

Set sail for an unforgettable evening aboard the River Star or Island Time, where the drinks are flowing and the views are unmatched. Enjoy a...

1 hour 15 minutes
4.9 (26)
from
$42
Private Chicago Loop Architecture Walking Tour

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic …More

Chicago, USA

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic...

120 to 150 minutes Free Cancellation
5.0 (22)
from
$71
Explore the Historic Old Post Office in Chicago

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 …More

Chicago, USA

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...

1 hour 30 minutes Free Cancellation
5.0 (27)
from
$15
Skyline Lakefront and Millennium Park Chicago Private Day Tour

Explore Chicago’s iconic landmarks and scenic lakefront on a private, fully personalized city tour. Travel in comfort with your English-speaking driver, who shares local stories, …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA

Explore Chicago’s iconic landmarks and scenic lakefront on a private, fully personalized city tour. Travel in comfort with your English-speaking driver, who shares local stories,...

3 hours Hotel pickup offered Free Cancellation
5.0 (1)
from
$58
Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hancock …More

Chicago, USA

On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hancock...

3 hours Free Cancellation
5.0 (3)
from
$109
Haunted Chicago: Lincoln Park Ghost & History Walking Tour

This isn’t just a ghost tour, it’s a story-driven walk through one of Chicago’s most haunted landscapes, where real history and local legend collide. Unlike …More

Chicago, USA

This isn’t just a ghost tour, it’s a story-driven walk through one of Chicago’s most haunted landscapes, where real history and local legend collide. Unlike...

1 hour 30 minutes Free Cancellation
4.3 (13)
from
$30
The Art Institute in Chicago Highlights Tour & Photoshoot

Discover the Art Institute in a unique way that blends art, storytelling, and photography. After a warm welcome, we'll head inside with tickets included & …More

Chicago, USA

Discover the Art Institute in a unique way that blends art, storytelling, and photography. After a warm welcome, we'll head inside with tickets included &...

1 hour 15 minutes Free Cancellation
5.0 (5)
from
$101
Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking …More

Chicago, USA

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking...

2 hours Free Cancellation
5.0 (7)
from
$50
Chicago Architecture River Tour & Hop-on Hop-off Sightseeing Tour

Save 20% when you bundle these two iconic Chicago experiences! Discover Chicago by road and river with a 48-hour Hop-on Hop-off Ticket and Shoreline Architecture …More

Chicago, USA

Save 20% when you bundle these two iconic Chicago experiences! Discover Chicago by road and river with a 48-hour Hop-on Hop-off Ticket and Shoreline Architecture...

2 hours Free Cancellation
4.5 (46)
from
$99
The Chicago Theatre Tour Experience

A 60-75-minute guided, behind-the-scenes exploration of the historic Chicago Theatre, one of the city’s most iconic landmarks. Stand on the famed Chicago theatre stage and …More

Chicago, USA

A 60-75-minute guided, behind-the-scenes exploration of the historic Chicago Theatre, one of the city’s most iconic landmarks. Stand on the famed Chicago theatre stage and...

60 to 75 minutes
4.3 (46)
from
$32
Prairie Avenue Haunted History Tour and Ghost Hunt

Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this …More

Chicago, USA

Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this...

2 hours 20 minutes
5.0 (12)
from
$44
Chicago Movie Locations Tour

Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigley Field exterior …More

Chicago, USA

Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigley Field exterior...

3 hours Hotel pickup offered Free Cancellation
5.0 (11)
from
$315
Custom Chicago Walking Tours

We create custom walking tours for groups of all sizes and interests, blending delicious food experiences with rich historical storytelling. From downtown explorations for high …More

Chicago, USA

We create custom walking tours for groups of all sizes and interests, blending delicious food experiences with rich historical storytelling. From downtown explorations for high...

1 to 3 hours Free Cancellation
5.0 (5)
from
$75
Explore Chicago Black Culinary Heritage

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s …More

Chicago, USA

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s...

2 hours 45 minutes Free Cancellation
5.0 (6)
from
$75
Chicago Private Neighborhoods Tour to Lincoln and Hyde Park

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares local …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares local...

4 hours Hotel pickup offered Free Cancellation
5.0 (1)
from
$78

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These answers are based on answers previously given to City Sky Diving customers' questions.

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