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Top Illinois Full-day Tours

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Illinois Tours

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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
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
Frank Lloyd Wright Tour in Oak Park

Exploring Oak Park, Illinois, where Frank Lloyd Wright resided during the crucial early years of his career, offers a captivating journey through the evolution of …More

4.6 (15)

Frank Lloyd Wright Tour in Oak Park

Exploring Oak Park, Illinois, where Frank Lloyd Wright resided during the crucial early years of his career, offers a captivating journey through the evolution of...

1 hour • Free Cancellation
4.6 (15)
from
$35
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
Chicago, USA
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 to Milwaukee Day Trip with Brewery Tour & City Highlights

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davidson Museum, …More

Chicago, USA
4.5 (15)

Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davidson Museum,...

8 to 10 hours • Free Cancellation
4.5 (15)
from
$125
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

Chicago, USA
5.0 (26)

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...

1 hour 30 minutes • Free Cancellation
5.0 (26)
from
$15
Chicago Movie Locations Tour

Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigley Field exterior …More

Chicago, USA
5.0 (11)

Chicago Movie Locations Tour

Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigley Field exterior...

3 hours • Hotel pickup offered • Free Cancellation
5.0 (11)
from
$315
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

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...

8 to 12 hours • Hotel pickup offered • Free Cancellation
5.0 (6)
from
$149
Shameless TV Show Location Tour

Experience the ultimate Private Shameless TV Location Tour with the convenience of hotel pick and drop-off, allowing you to sit back, relax and enjoy the …More

Chicago, USA
5.0 (5)

Shameless TV Show Location Tour

Experience the ultimate Private Shameless TV Location Tour with the convenience of hotel pick and drop-off, allowing you to sit back, relax and enjoy the...

2 hours • Hotel pickup offered • Free Cancellation
5.0 (5)
from
$315
Iconic Action Film and Movie Locations 1 Day Tour in Chicago

From the Gotham chaos in The Dark Knight to the explosive battles of Transformers, Chicago’s skyline has played a starring role in countless blockbusters. On …More

Chicago, USA
5.0 (3)

Iconic Action Film and Movie Locations 1 Day Tour in Chicago

From the Gotham chaos in The Dark Knight to the explosive battles of Transformers, Chicago’s skyline has played a starring role in countless blockbusters. On...

9 hours • Free Cancellation
5.0 (3)
from
$158
Guided Seasonal Hike

Discover Starved Rock’s canyons, bluffs and seasonal waterfalls on this 3-mile (round trip) guided hike. Listen as the guide tells stories of how Starved Rock …More

5.0 (1)

Guided Seasonal Hike

Discover Starved Rock’s canyons, bluffs and seasonal waterfalls on this 3-mile (round trip) guided hike. Listen as the guide tells stories of how Starved Rock...

4 hours • Free Cancellation
5.0 (1)
from
$33
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

Chicago, USA
5.0 (1)

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...

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

Chicago, USA
4.0 (4)

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...

8 to 10 hours • Free Cancellation
4.0 (4)
from
$194
One Day Galena and Dubuque Tour from Chicago

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, …More

Chicago, USA
3.0 (2)

One Day Galena and Dubuque Tour from Chicago

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque,...

9 to 10 hours • Hotel pickup offered • Free Cancellation
3.0 (2)
from
$315
Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenient …More

Chicago, USA

Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenient...

9 to 10 hours • Hotel pickup offered • Free Cancellation
from
$1,200
Discover Chicago: A Self-Guided Walking Tour

Discover Chicago's soaring ambition and neighborhood soul with your self-guided audio tour, allowing you to explore America's most architecturally significant city at your own pace. …More

Chicago, USA

Discover Chicago: A Self-Guided Walking Tour

Discover Chicago's soaring ambition and neighborhood soul with your self-guided audio tour, allowing you to explore America's most architecturally significant city at your own pace....

8 hours 30 minutes • Free Cancellation
from
$4

Frequently Asked Questions

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

Recent tour reviews
Fun day in Chicago
New York City
Iconic Action Film and Movie Locations 1 Day Tour in Chicago
873yued, Sep 2026
Fun day in Chicago
Really enjoyed this tour! It was a fun way to explore Chicago and see some iconic movie locations. Michael was friendly, knowledgeable, and made the whole experience really enjoyable. Everything was well organized and easy. Definitely recommend if you’re a movie fan or just want to see a different side of Chicago!
Read more
VIP Tour 4 Sure!
New York City
Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights
858yihanl, Sep 2026
VIP Tour 4 Sure!
Me and my husband joined the Chicago-Milwaukee one day tour.It is a phenomena experience with our Tour Guide Mike, he is very professional, personable, and knowledgeable. We learned a lot from this TOUR. I will highly recommend this company to the future tourist you will not be regret. What a day!!
Read more
What started out as...
New York City
Shameless TV Show Location Tour
Emily_M, Sep 2026
What started out as...
What started out as discouraging because of my arriving late to our pick up point due to traffic/rain became the most amazing time with Deenil Experiences and his flexibility with us. We were scheduled for a Shameless Tour, but after some nice conversations, we ended up getting to see other movie locations that weren’t on our itinerary. We were even dropped off at the famous Mr. Beef where we had lunch and were able to enjoy the rest of the day.
Read more
Old Post Office Walking Tour
New York City
Explore the Historic Old Post Office in Chicago
Compass25189952749, Sep 2026
Old Post Office Walking Tour
Excellent tour given by our guide Sandy. Her enthusiasm and knowledge of the Post Office was unsurpassed.
Read more
Great !!
New York City
Iconic Action Film and Movie Locations 1 Day Tour in Chicago
193kariem, Sep 2026
Great !!
Michael did such a great. I couldn’t be happier
Read more
Great tour
New York City
Chicago Suburbs Hidden Gems: Small-Group Exploration Tour
Kate_O, Aug 2026
Great tour
We had a great time. Tour was private- just us and a guide Kris. Kris was very friendly and knowledgeable. Visited beautiful places. Highly recommended
Read more
Great Tour of Chicago
New York City
Skyline Lakefront and Millennium Park Chicago Private Day Tour
Twana_J, Aug 2026
Great Tour of Chicago
Was on time in a nice clean vehicle, ease to each location, no rush, we were able to take our time at each site. Offered additional sites. Had a great time
Read more
Fun way to experience Milwaukee
New York City
Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights
Trip07439410915, Aug 2026
Fun way to experience Milwaukee
A must-do experience in Milwaukee! The brewery tour was more interesting than expected, with a great mix of brewing history, local culture, and beer tasting. The atmosphere was relaxed and enjoyable, making it a fun way to experience Milwaukee.
Read more
Exceeded our...
New York City
Chicago Movie Locations Tour
Carolyn_L, Aug 2026
Exceeded our...
Exceeded our expectations!! Luxury SUV well-maintained. Courteous driver/guide. Extremely knowledgeable about all areas of Chicago. We saw and had photo ops at all the movie locations listed in the description of tour. We also drove by and learned about various neighborhoods in Chicago and suburbs as well as many points of interest along the way. Exceptional drive and tour guide who went above and beyond the norm. I can’t say enough good things about this great afternoon we spent seeing and learning about Chicago!!!
Read more
A relaxing morning sail on Lake Michigan
New York City
Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago
rusty_stein, Aug 2026
A relaxing morning sail on Lake Michigan
Captain Ulysses was great. Fun, friendly, and very responsible. Good communication leading up to the trip. A beautiful way to see the Chicago skyline.
Read more
Fantastic!
New York City
Shameless TV Show Location Tour
944kristophert, Aug 2026
Fantastic!
Deen picked us up from our lunch spot and was so knowledgeable. We visited Shiela’s, the Milkovich’s, Gallagher’s, Fiona’s building, the public downtown library, and the bean! Totally worth every penny!
Read more
A+! We loved every minute.
New York City
Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago
Jennifer_G, Jul 2026
A+! We loved every minute.
We LOVED our sailing excursion with Captain Ulysses! 6 of us went during a girls weekend, and it was the absolute highlight of our trip. Captain Mike and Captain Ulysses got us on board right on time, and we enjoyed two hours of sailing with great wind and a ton of excitement. If you’re considering booking, DO IT. As a group of moms, we tend to spend our girls trips catching up and reminiscing, and not always making NEW fun memories together. This was exactly what we needed, and we’ll remember this outing forever. We were begging to buy out the next hour, but someone already had it booked. We’d absolutely do it again! Thank you for a great time!
Read more
Oak Park walking tour
New York City
Frank Lloyd Wright Tour in Oak Park
cml2381, Jul 2026
Oak Park walking tour
Great walking tour! Our guide Liz was engaging, knowledgeable, and passionate about Oak Park’s architecture. Even though the tour did not include interiors of the homes, Liz had visited many of the houses and shared her experience. Also grateful for her tip to visit the Frank Lloyd Wright Trust. Highly recommend.
Read more
Alice’s Amazing Post Office Tour
New York City
Explore the Historic Old Post Office in Chicago
H7333BHjulied, Jul 2026
Alice’s Amazing Post Office Tour
Tour guide Alice was marvelous. She was animated, energetic, personable, and incredibly well – informed. Would highly recommend both the fascinating tour and her leadership.
Read more
Cool place to visit
New York City
Frank Lloyd Wright Tour in Oak Park
TLG056, Jul 2026
Cool place to visit
Note that Cool Destinations was acting funky as I was writing this review. We just toured the Center itself.There was an exhibit on making buildings safer for birds, and another exhibit on Wrigley Field. Both were very informative.
Read more
Private Tour
New York City
Chicago Suburbs Hidden Gems: Small-Group Exploration Tour
FENESA_r, Jul 2026
Private Tour
I opted for the private tour with Kris, who pulled up in a black drop-top Corvette. 😎🏎️ I have to tell you, Kris is just cool and laid-back. It honestly felt like I was riding around with someone I'd known for years.He took me directly to all the must-see spots, gave me plenty of time to take pictures, and made the entire experience feel relaxed and enjoyable.The best part? It never felt like an eight-hour tour. Between the top being down, the wind blowing, great conversation, and all the beautiful places we visited, the day flew by.The only place I wish I'd had more time to explore was the Botanical Gardens, but that's not the tour's or Kris's fault. That place is absolutely massive and stunning!I would absolutely book this tour again. Highly recommend it! 🌿📸✨
Read more
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