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Top Chicago Tours & Sightseeing

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

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 Lakefront Electric Bike Tour

This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will …More

Likely to Sell Out
Likely to Sell Out

This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will...

45 to 60 minutes Free Cancellation
5.0 (15)
from
$69
Chicago Half-Day Bike Rental

Explore Chicago at your own pace on an independent bike tour. With your half-day bike rental, pedal along Lake Michigan and visit top Chicago attractions …More

Likely to Sell Out
Likely to Sell Out

Explore Chicago at your own pace on an independent bike tour. With your half-day bike rental, pedal along Lake Michigan and visit top Chicago attractions...

4 hours Free Cancellation
4.7 (12)
from
$20
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

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

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
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

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
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

Likely to Sell Out
Likely to Sell Out

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
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

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
Field Museum of Natural History Early Access Ticket

Visit the Field Museum like a VIP on this one- hour early access VIP tour. Head inside the Field Museum at 8am before it opens …More

Visit the Field Museum like a VIP on this one- hour early access VIP tour. Head inside the Field Museum at 8am before it opens...

2 to 4 hours Free Cancellation
4.7 (57)
from
$73
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

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
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

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
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

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
Outdoor Escape Room in Chicago - Fulton Market

An immersive clue-solving adventure around the trendy arts neighborhood Fulton Market. Search for real-world clues, solve puzzles, and discover the neighborhood with an experience you'll …More

An immersive clue-solving adventure around the trendy arts neighborhood Fulton Market. Search for real-world clues, solve puzzles, and discover the neighborhood with an experience you'll...

2 hours
4.9 (33)
from
$75
Private Chicago City Minibus Tour

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on …More

Likely to Sell Out
Likely to Sell Out

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on...

2 hours Hotel pickup offered Free Cancellation
5.0 (1)
from
$999
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

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
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

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
Private Chicago Foodie Tour

Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza, …More

Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza,...

4 hours Free Cancellation
5.0 (6)
from
$288
Private Vacation Photoshoot with Photographer in Chicago

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing …More

Likely to Sell Out
Likely to Sell Out

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing...

1 hour Free Cancellation
4.0 (4)
from
$137
Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables, …More

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables,...

2 hours
4.8 (4)
from
$87
Private Chicago Architecture Walking Tour

Discover the heart of Chicago’s architectural legacy on this guided walking tour through the historic Loop District. Step back in time as you explore some …More

Discover the heart of Chicago’s architectural legacy on this guided walking tour through the historic Loop District. Step back in time as you explore some...

3 hours Free Cancellation
4.8 (6)
from
$211

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These answers are based on answers previously given to Cool Shore Excursions customers' questions.

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