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Top Chicago City Tours

Chicago City Tours See It All No Time Wasted

Skip the corny jokes and never-ending speeches — our shared tours are built for travelers who want the real Chicago, not a stand-up routine. ✔️ …More

Skip the corny jokes and never-ending speeches — our shared tours are built for travelers who want the real Chicago, not a stand-up routine. ✔️...

4 to 8 hours Free Cancellation
4.3 (20)
from
$150
Chicago Private Night Skyline and Lakefront Scenic Tour

Experience Chicago’s glowing skyline and scenic lakefront on a private, fully personalized night tour. Travel in comfort with your English-speaking driver, who shares stories and …More

Likely to Sell Out
Likely to Sell Out

Experience Chicago’s glowing skyline and scenic lakefront on a private, fully personalized night tour. Travel in comfort with your English-speaking driver, who shares stories and...

2 hours Hotel pickup offered Free Cancellation
3.0 (2)
from
$34
4-Hour Chicago City Tour by SUV

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

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

4 hours Hotel pickup offered Free Cancellation
5.0 (2)
from
$800
️ Chicago Instagram Walking Tour (Private & All- Inclusive)

Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a …More

Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a...

4 hours Free Cancellation
5.0 (2)
from
$236
Private Chicago Guided Tour with Hotel Pickup

One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour …More

One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour...

4 hours Hotel pickup offered Free Cancellation
5.0 (4)
from
$179
Private Wicker Park and Bucktown Walking Tour

This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time …More

This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time...

2 hours 30 minutes Free Cancellation
5.0 (3)
from
$195
5-Day Tour of Superior, Huron and Michigan from Chicago

Five days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are …More

Five days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are...

5 days Free Cancellation
5.0 (3)
from
$1,180
Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

Take in three of the Great Lakes and a string of classic Midwest towns on this four-day small-group loop out of Chicago. Travel up the …More

Take in three of the Great Lakes and a string of classic Midwest towns on this four-day small-group loop out of Chicago. Travel up the...

4 days Free Cancellation
5.0 (3)
from
$995
Private City Tour 6-10ppl

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 10 PASSENGERS TOTAL.  Thank you for contacting Chicago Private Tours! We would love to help …More

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 10 PASSENGERS TOTAL.  Thank you for contacting Chicago Private Tours! We would love to help...

3 to 4 hours Hotel pickup offered Free Cancellation
5.0 (3)
from
$770
Chicago Gangster History Walking Tour of River North

Go beyond Capone. An expert guides uncovers the Beer Wars, the ambushes, and the brutal rivalries on these exact streets. …More

Go beyond Capone. An expert guides uncovers the Beer Wars, the ambushes, and the brutal rivalries on these exact streets....

2 hours Free Cancellation
4.8 (4)
from
$30
Downtown Chicago City Tour In a Lamborghini[60 Minute Experience]

Experience Chicago in unparalleled style with a 10-mile cruise through the city in a luxury or exotic vehicle. Glide through iconic streets, turning heads at …More

Experience Chicago in unparalleled style with a 10-mile cruise through the city in a luxury or exotic vehicle. Glide through iconic streets, turning heads at...

45 to 60 minutes
5.0 (2)
from
$99
Chicago's Gold Coast Hidden History: A Self-Guided Audio Tour

Where did Chicago’s millionaires live, love and misbehave? Walk the Gold Coast with historian Amy Bizzarri, author of 111 Places in Chicago That You Must …More

Where did Chicago’s millionaires live, love and misbehave? Walk the Gold Coast with historian Amy Bizzarri, author of 111 Places in Chicago That You Must...

50 minutes Free Cancellation
4.6 (7)
from
$9
Chicago 6-Hour City Tour by Sedan

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

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

6 hours Hotel pickup offered Free Cancellation
5.0 (1)
from
$960
2 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get …More

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get...

2 hours Free Cancellation
5.0 (1)
from
$89
Luxury SUV 4 Hour Sightseeing Tour

Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking parks, …More

Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking parks,...

2 to 4 hours Hotel pickup offered Free Cancellation
4.5 (2)
from
$350
Chicago Small Group City Tour

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods …More

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods...

9 to 10 hours Hotel pickup offered Free Cancellation
5.0 (1)
from
$340
Chicago, Cloud Gate, Grant Park Full-Day City Tour

Discover Chicago, a vibrant city set along the shores of Lake Michigan, known for its world-class architecture, iconic skyline, and rich cultural scene. As the …More

Discover Chicago, a vibrant city set along the shores of Lake Michigan, known for its world-class architecture, iconic skyline, and rich cultural scene. As the...

8 to 10 hours Free Cancellation
4.0 (4)
from
$194
Chicago Amazing Lakefront Bike Tour

Enjoy the car-free lakefront trail and explore Chicago’s beaches, parks, lagoons, This tour offers a diverse mix of nature and attractions. Top sights include: The …More

Enjoy the car-free lakefront trail and explore Chicago’s beaches, parks, lagoons, This tour offers a diverse mix of nature and attractions. Top sights include: The...

1 hour 30 minutes Free Cancellation
3.6 (8)
from
$49
Continental US Train Zephyr Adventure CA -CO - Il

Embark on the adventure of a lifetime! Step aboard the iconic California-Chicago Train Expedition as we whisk you away on a journey that combines the …More

Embark on the adventure of a lifetime! Step aboard the iconic California-Chicago Train Expedition as we whisk you away on a journey that combines the...

3 days Free Cancellation
4.0 (1)
from
$5
Chicago Exotic Auto Experience

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride …More

Likely to Sell Out
Likely to Sell Out

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride...

3 to 7 hours
from
$1,800

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

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