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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

Likely to Sell Out
Likely to Sell Out
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
$7
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
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 (341)

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 (341)
from
$84
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 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 (126)

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 (126)
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
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 (200)

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 (200)
from
$539
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 (24)

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 (24)
from
$33
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
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

5.0 (14)

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...

120 to 150 minutes • Hotel pickup offered • Free Cancellation
5.0 (14)
from
$71
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
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

4.8 (4)

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,...

2 hours
4.8 (4)
from
$87

Frequently Asked Questions

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

Recent tour reviews
Wonderful Stories
New York City
Art Institute of Chicago Private Expert Guided Tour
saraheK527UH, Sep 2026
Wonderful Stories
Joel was a fabulous guide. I loved how he made the art come to life with stories about the artists and their relationships to each other.
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
Skip the other options-this is the tour you want
New York City
Art Institute of Chicago Skip-the-Line Exclusive Guided Tour
suefK8078LY, Sep 2026
Skip the other options-this is the tour you want
One of the best tours we've taken. We don't know much about art and Samantha was amazing! She taught us so much while we enjoyed the overwhelming museum! While we waited, other tours gathered in the same spot. First two guides were nice, but general tour guides. One of them also guides the food tours. Each group had maybe 15 people. Then here comes Samantha, a graduate of the art institute in art history. Four people on our tour. Yes we hit the highlights but she also personalized it. She was fun and interesting. We walked away feeling like we were the lucky ones and can't stop talking about our morning. Cannot recommend Babylon enough.
Read more
This tour made me more interested in the history of the building.
New York City
Private Chicago Loop Architecture Walking Tour
kularats, Sep 2026
This tour made me more interested in the history of the building.
My English isn’t that good, but I really tried to concentrate. This tour amazed me! 🥹
Read more
Perfect
New York City
Private Chicago Loop Architecture Walking Tour
marcelamW5752VL, Sep 2026
Perfect
Amazing tour highly recommend!
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
Excellent Tour
New York City
Art Institute of Chicago Skip-the-Line Exclusive Guided Tour
Petlovers, Sep 2026
Excellent Tour
Spiro was a wonderful guide. He was extremely knowledgeable about the art and my friends and I learned a lot from him. We thoroughly enjoyed the tour.
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
A Great Afternoon with an Exceptional Guide
New York City
Art Institute of Chicago Private Expert Guided Tour
P1647AJmikes, Sep 2026
A Great Afternoon with an Exceptional Guide
Mark Collin’s was a fantastic guide. He has an incredible depth of knowledge built over a lifetime of studying and teaching art, and he’s an excellent artist himself. What we enjoyed most was his obvious passion for the subject. He’s personable, friendly, and just a really interesting guy to spend time with. We thoroughly enjoyed getting to know him, and he made it a great afternoon. I’d highly recommend Mark to anyone looking for a truly memorable tour.
Read more
Don’t miss this tour!
New York City
Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour
Lisa_K, Sep 2026
Don’t miss this tour!
Dan was amazing! He was full of energy, stories and great locations! The time flew by! We had a great time.
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
Knowledgeable Guide - Great Value
New York City
History and Architecture of Chicago Loop Walking Tour
emorym209, Sep 2026
Knowledgeable Guide - Great Value
My husband are the only ones to her and it was absolutely wonderful. We love architecture and our guide was able to go into much better detail than he normally would and we got so much out of it. Highly recommend this guide he was exceptionally knowledgeable and very friendly.
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
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