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Top Chicago Private Sightseeing Tours

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Chicago Tours

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Private 45-Minute Chicago Skyline Helicopter Tour

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 …More

Likely to Sell Out
Likely to Sell Out
4.9 (126)

Private 45-Minute Chicago Skyline Helicopter Tour

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...

45 minutes • Free Cancellation
4.9 (126)
from
$849
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

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 …More

5.0 (71)

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

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...

2 hours • Free Cancellation
5.0 (71)
from
$508
Haunted Chicago: Lincoln Park Ghost Escape Game

A dating app. A stranger with arctic blue eyes. A meeting in Lincoln Park on Halloween. This self-guided ghost escape game drops you into Chicago's …More

4.0 (6)

Haunted Chicago: Lincoln Park Ghost Escape Game

A dating app. A stranger with arctic blue eyes. A meeting in Lincoln Park on Halloween. This self-guided ghost escape game drops you into Chicago's...

2 hours • Free Cancellation
4.0 (6)
from
$6
Pilsen Chicago Walking Tour: Street Art & Mexican History

Discover Pilsen, one of Chicago’s most vibrant neighborhoods, known for its colorful street art, rich Mexican heritage, historic architecture, and thriving local culture. This locally …More

5.0 (6)

Pilsen Chicago Walking Tour: Street Art & Mexican History

Discover Pilsen, one of Chicago’s most vibrant neighborhoods, known for its colorful street art, rich Mexican heritage, historic architecture, and thriving local culture. This locally...

1 hour 15 minutes • Free Cancellation
5.0 (6)
from
$35
Private Chicago Food Tour with Deep Dish and Beef Sandwich

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all …More

Likely to Sell Out
Likely to Sell Out
5.0 (87)

Private Chicago Food Tour with Deep Dish and Beef Sandwich

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all...

3 hours • Free Cancellation
5.0 (87)
from
$160
Art Institute of Chicago Skip-the-Line Exclusive Guided Tour

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 …More

5.0 (346)

Art Institute of Chicago Skip-the-Line Exclusive Guided Tour

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...

2 hours 30 minutes • Free Cancellation
5.0 (346)
from
$84
Art Institute of Chicago Private Expert Guided Tour

Let our expert local guides share their passion with you for The Art Institute of Chicago on this private 2 hour tour. As you traverse …More

5.0 (128)

Art Institute of Chicago Private Expert Guided Tour

Let our expert local guides share their passion with you for The Art Institute of Chicago on this private 2 hour tour. As you traverse...

2 hours • Free Cancellation
5.0 (128)
from
$80
Private Magnificent Mile Architecture Tour and 360 Chicago Ticket

Experience the story of Chicago through its skyline on a walking tour that stretches from the city’s 19th-century roots to its most striking modern towers. …More

4.9 (80)

Private Magnificent Mile Architecture Tour and 360 Chicago Ticket

Experience the story of Chicago through its skyline on a walking tour that stretches from the city’s 19th-century roots to its most striking modern towers....

2 hours • Free Cancellation
4.9 (80)
from
$99
Private Chicago History Museum Tour

Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life …More

5.0 (27)

Private Chicago History Museum Tour

Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life...

2 hours • Free Cancellation
5.0 (27)
from
$59
Lincoln Park Zoo & Nature Museum Private Tour

Discover the wild heart of Chicago on our guided walking tour through Lincoln Park, where nature and history meet in one unforgettable experience. What sets …More

5.0 (21)

Lincoln Park Zoo & Nature Museum Private Tour

Discover the wild heart of Chicago on our guided walking tour through Lincoln Park, where nature and history meet in one unforgettable experience. What sets...

2 hours • Free Cancellation
5.0 (21)
from
$275
Chicago City Private Tours

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a …More

4.8 (41)

Chicago City Private Tours

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a...

2 to 8 hours • Hotel pickup offered • Free Cancellation
4.8 (41)
from
$199
History and Architecture of Chicago Loop Walking Tour

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walk among gigantic towers of downtown and learn how Chicago became …More

5.0 (27)

History and Architecture of Chicago Loop Walking Tour

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walk among gigantic towers of downtown and learn how Chicago became...

2 hours • Free Cancellation
5.0 (27)
from
$33
Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  Thank you for contacting Chicago Private Tours! We would love to help your …More

5.0 (201)

Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  Thank you for contacting Chicago Private Tours! We would love to help your...

3 to 4 hours • Hotel pickup offered • Free Cancellation
5.0 (201)
from
$539
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
5.0 (15)

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...

45 to 60 minutes • Free Cancellation
5.0 (15)
from
$69
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

5.0 (77)

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...

3 hours • Free Cancellation
5.0 (77)
from
$85
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

5.0 (3)

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...

3 hours • Free Cancellation
5.0 (3)
from
$109
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
4.3 (8)

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....

5 hours • Hotel pickup offered • Free Cancellation
4.3 (8)
from
$79
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
5.0 (1)

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...

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
5.0 (1)

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,...

3 hours • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$59
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

5.0 (6)

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,...

4 hours • Free Cancellation
5.0 (6)
from
$288

Frequently Asked Questions

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

Recent tour reviews
Loved it!
New York City
Art Institute of Chicago Private Expert Guided Tour
susanhZ8320JH, Sep 2026
Loved it!
Brian was very knowledgeable !
Read more
Incredible tour, incredible guide. Do this tour!
New York City
Art Institute of Chicago Skip-the-Line Exclusive Guided Tour
panblanc0, Sep 2026
Incredible tour, incredible guide. Do this tour!
Fabulous venue, incredible art, spectacular building. Our guide Spiro was outstanding. I learned more about art history and the relationships across ages and countries than ever before. I highly recommend Babylon and Spiro as your guide is a must.
Read more
Excellent guide
New York City
Art Institute of Chicago Skip-the-Line Exclusive Guided Tour
jenmil123, Sep 2026
Excellent guide
Mandy was such a wonderful guide. She is extremely knowledgeable and has a real passion for what she does. She knows secrets about the paintings and makes the tour fun. I can see where she would be really good with families. I recommend you ask for her specifically!
Read more
Chicago’s history comes alive in this tour
New York City
History and Architecture of Chicago Loop Walking Tour
Natashenanigans, Sep 2026
Chicago’s history comes alive in this tour
Dave is a spectacular guide! Chicago is a beautiful city but he really made it come alive. In about two hours, he is able to describe the city’s incredible journey through history, starting with the small settlement in the early 1800s to its exponential growth, to the booming metropolis it is today. Along the journey, he takes you through important and beautiful places that exemplify the city’s unique development through the ages. We were able to understand Chicago better and appreciate how much has gone into making it what it is now. Dave is also super personable and passionate and is able to engage in any question. We wholeheartedly recommend this tour to anyone who is visiting and wants a stellar introduction to the city.
Read more
fabulous museum and Awesome guide .. Don't miss the opportunity.
New York City
Art Institute of Chicago Private Expert Guided Tour
JeanOnTheRun, Sep 2026
fabulous museum and Awesome guide .. Don't miss the opportunity.
Our tour of the Art Institute of Chicago was awesome. Joe (our guide) was so knowledgeable and he was eager to share it with us. It was a delightful way to get an "introduction" to the museum. There is so much to see ... we will come back and seek out Joe for another tour .. jean
Read more
This was a great way to...
New York City
Chicago Private Custom City Tour with Hotel Pick Up
capotvin, Sep 2026
This was a great way to...
This was a great way to see the city the way you want. Our tour guide, Sofia, and our driver, J T were great and gave us lots of information. If you are in Chicago for the first time, I highly recommend this tour.
Read more
Discovering Chicago
New York City
History and Architecture of Chicago Loop Walking Tour
elizabethaR3092VJ, Sep 2026
Discovering Chicago
Dave is knowledgeable, personable and gave us a delightful tour of many historic buildings. We learned a lot about pivotal moments in Chicago’s past, including interesting anecdotes about local personalities that influenced the development of the city. Time well spent!
Read more
Such a great tour, don't miss it!
New York City
Pilsen Chicago Walking Tour: Street Art & Mexican History
noragP7303YI, Sep 2026
Such a great tour, don't miss it!
This was such a wonderful and informative tour. Luis our guide was outstanding! His knowledge of the history of the neighborhood, the artists, and the subjects of the murals was vast. He made it such an interesting experience. I'm so glad I went on this tour!
Read more
Great tour
New York City
Chicago Private Custom City Tour with Hotel Pick Up
elizabethmX9186LB, Sep 2026
Great tour
Matthew is a knowledgeable tour guide. I will definitely recommend this tour.
Read more
A lot of food
New York City
Private Chicago Food Tour with Deep Dish and Beef Sandwich
geoffreym354, Sep 2026
A lot of food
Come hungry... deep dish pizza, hotdogs, Italian beef and sweets. Its a lot! Elliott did a really nice job sharing food and architectural history with us
Read more
Don’t miss this excursion!!
New York City
Pilsen Chicago Walking Tour: Street Art & Mexican History
Esther_D, Sep 2026
Don’t miss this excursion!!
Luis, our guide was very knowledgeable and enthusiastic . He explained the murals and their significance in this neighborhood!
Read more
Chicago Bob & Food - great combo!
New York City
Private Chicago Food Tour with Deep Dish and Beef Sandwich
Lisa M, Sep 2026
Chicago Bob & Food - great combo!
Our guide, Chicago Bob, was great. Knowledgeable and made it fun. It was a small group and he read things well - explaining and letting us all talk amongst ourselves. The food samples were very filling and his facts were great. I’d highly recommend doing this!
Read more
Great tour!
New York City
Lincoln Park Zoo & Nature Museum Private Tour
Y3892OVharryg, Sep 2026
Great tour!
I went with my 10-year old daughter, and we both had a blast. The butterfly garden, seeing the baby zebra and rhino at the zoo, it was all awesome. The tour guide was funny and engaging for adults and kids. Highly recommend!!!
Read more
Positively “Wright”!
New York City
Frank Lloyd Wright Oak Park Architecture Tour from Chicago
Elizabeth_B, Sep 2026
Positively “Wright”!
Perfect pickup and delivery to the FLWright sites in the Trust; however, it would have been good to know more clearly that the tours had specific times because we were a little late for the start of the Robie House tour.
Read more
Zoo review
New York City
Lincoln Park Zoo & Nature Museum Private Tour
Linda_M, Sep 2026
Zoo review
Our guide Scout, was extremely well versed in all aspects of the Museum and Zoo. We had plenty of time, and she took great care in explaining the plants, butterflies, reptiles, and animals. I would highly recommend this tour and do ask for Scout as your guide. Exceptional.
Read more
Excellent way to take in...
New York City
Private Chicago History Museum Tour
Therese_M, Sep 2026
Excellent way to take in...
Excellent way to take in The Chicago History Museum with an extremely knowledgeable, personable guide.
Read more
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