Top Illinois Private Sightseeing Tours

Q: Which Illinois Private Sightseeing Tours have Instant Confirmation?

Illinois Private Sightseeing Tours with Instant Confirmation include: Hyde Park Walking Tour History Race and Urban Change Continental US Train Zephyr Adventure CA -CO - Il Chicago Self-Guided Audio Tour Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago Land of Lincoln Smartphone Audio APP Self Guided Walking Tour View all Tours with Instant Confirmation →

Q: Got any more Illinois trip ideas?

We sure do. Check out our curated lists of hand-picked Illinois Tours. Top 10 Illinois 2026 Senior-friendly tours Illinois The best tours and activities for culture lovers in Illinois Top Day Trips from Illinois Things to do in Illinois this summer View all Illinois Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Illinois?

Based on our sales data over the past year, the most popular styles of tours and activities in Illinois are: Illinois Luxury & Special Occasions Illinois Luxury Tours Illinois Tours & Sightseeing Illinois Cruises, Sailing & Water Tours Illinois Boat Tours View all tour styles in Illinois →

Field Museum of Natural History Chicago Tour with Tickets

Skip the lines and uncover ancient wonders at Chicago’s Field Museum, home to SUE, the world’s most complete T. rex. Marvel at dazzling artifacts, real …More

Chicago, USA

5.0 (2)

Field Museum of Natural History Chicago Tour with Tickets

Skip the lines and uncover ancient wonders at Chicago’s Field Museum, home to SUE, the world’s most complete T. rex. Marvel at dazzling artifacts, real...

2 hours Free Cancellation

5.0 (2)

from
$113

The Bear Private Pedicab Food Tour of Chicago

If you want culture, history, food, cinema and film and a heavy dose of all things Chicago this is your tour! Get ready to EAT. …More

Chicago, USA

5.0 (1)

The Bear Private Pedicab Food Tour of Chicago

If you want culture, history, food, cinema and film and a heavy dose of all things Chicago this is your tour! Get ready to EAT....

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$130

Chicago Suburbs Hidden Gems: Small-Group Exploration Tour

Experience a global adventure without leaving Chicagoland! This tour blends rich cultural landmarks, stunning natural beauty, and nostalgic favorites, creating a one-of-a-kind experience. *Hotel Pickup …More

Chicago, USA

5.0 (6)

Chicago Suburbs Hidden Gems: Small-Group Exploration Tour

8 to 12 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$149

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

Chicago, USA

5.0 (88)

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 (88)

from
$160

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

Chicago, USA

5.0 (4)

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...

4 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$178

Private History and Architecture of Chicago Loop Walking Tour

This is a private walking tour with your group and expert tour guide Dave Lineal. Different tour start times available upon request. I am happy …More

Chicago, USA

5.0 (1)

Private History and Architecture of Chicago Loop Walking Tour

This is a private walking tour with your group and expert tour guide Dave Lineal. Different tour start times available upon request. I am happy...

2 hours 30 minutes Free Cancellation

5.0 (1)

from
$180

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

Chicago, USA

5.0 (3)

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...

2 hours 30 minutes Free Cancellation

5.0 (3)

from
$195

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

Chicago, USA

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

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

Chicago, USA

4.8 (6)

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...

3 hours Free Cancellation

4.8 (6)

from
$211

️ 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

Chicago, USA

5.0 (2)

️ 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...

4 hours Free Cancellation

5.0 (2)

from
$236

Lincoln Park Zoo & Nature Museum Private Tour

Cover three Lincoln Park stops on a private walking tour through Chicago: the Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and Lincoln Park Zoo. At …More

Chicago, USA

5.0 (29)

Lincoln Park Zoo & Nature Museum Private Tour

Cover three Lincoln Park stops on a private walking tour through Chicago: the Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and Lincoln Park Zoo. At...

2 hours Free Cancellation

5.0 (29)

from
$275

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

Chicago, USA

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

Private Cultural Walking Tour in Chicago with Lakefront Landmarks

This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public art reflects …More

Chicago, USA

5.0 (1)

Private Cultural Walking Tour in Chicago with Lakefront Landmarks

This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public art reflects...

2 hours Free Cancellation

5.0 (1)

from
$349

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

Chicago, USA

4.5 (2)

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,...

2 to 4 hours Hotel pickup offered Free Cancellation

4.5 (2)

from
$350

Private Tour Art Institute of Chicago Guided Museum

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to …More

Chicago, USA

Private Tour Art Institute of Chicago Guided Museum

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to...

5 hours Hotel pickup offered

from
$443

Private Christmas Walking Tour in Chicago with Christkindlmarket

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are …More

Chicago, USA

5.0 (1)

Private Christmas Walking Tour in Chicago with Christkindlmarket

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are...

2 hours Free Cancellation

5.0 (1)

from
$469

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal …More

Chicago, USA

5.0 (3)

Private Holiday City Tour

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal...

3 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$499

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

Chicago, USA

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

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

Chicago, USA

5.0 (203)

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 (203)

from
$539

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

Chicago, USA

4 Hours of Chicago City Tour Sedan

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

4 hours Hotel pickup offered Free Cancellation

from
$640

Frequently Asked Questions

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

What are the best options for Illinois Private Sightseeing Tours?

What are the best kid-friendly options for Illinois Private Sightseeing Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Illinois Private Sightseeing Tours are:

View all kid-friendly Tours →

Which Illinois Private Sightseeing Tours have Instant Confirmation?

Which Illinois Private Sightseeing Tours have Free Cancellation?

Illinois Private Sightseeing Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Illinois Private Sightseeing Tours have Hotel Pickup?

No problem. These Illinois Private Sightseeing Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Illinois trip ideas?

What are the most popular styles of Tours and Activities in Illinois?