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Top Illinois City Tours

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Illinois Tours

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Chicago River 90-Minute Architecture Tour

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.8 (10,815)

Chicago River 90-Minute Architecture Tour

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to...

1 hour 30 minutes • Free Cancellation
4.8 (10,815)
from
$45
Chicago Lake and River Architecture Tour

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.8 (2,383)

Chicago Lake and River Architecture Tour

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years...

1 hour 30 minutes • Free Cancellation
4.8 (2,383)
from
$45
Chicago River 45-Minute Architecture Tour from Magnificent Mile

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.8 (3,452)

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich...

45 minutes • Free Cancellation
4.8 (3,452)
from
$28
Chicago Architecture River Cruise

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of …More

Chicago, USA
4.9 (16,512)

Chicago Architecture River Cruise

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of...

60 to 90 minutes • Free Cancellation
4.9 (16,512)
from
$39
Chicago Architecture Center River Cruise aboard First Lady

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only …More

Chicago, USA
4.9 (7,217)

Chicago Architecture Center River Cruise aboard First Lady

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only...

1 hour 30 minutes
4.9 (7,217)
from
$57
Lake Michigan Skyline Cruise in Chicago

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy stunning views …More

Chicago, USA
4.6 (893)

Lake Michigan Skyline Cruise in Chicago

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy stunning views...

30 to 45 minutes • Free Cancellation
4.6 (893)
from
$34
Lake Michigan Sunset Cruise in Chicago

The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.7 (1,582)

Lake Michigan Sunset Cruise in Chicago

The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago...

1 hour 30 minutes • Free Cancellation
4.7 (1,582)
from
$45
Chicago Sightseeing River and Lake Cruise

Our popular 90-minute daytime river and lake sightseeing tour delights family members of all ages with incredible views of Chicago's world-renowned buildings and stunning skyline. …More

Chicago, USA
4.8 (701)

Chicago Sightseeing River and Lake Cruise

Our popular 90-minute daytime river and lake sightseeing tour delights family members of all ages with incredible views of Chicago's world-renowned buildings and stunning skyline....

1 hour 30 minutes • Free Cancellation
4.8 (701)
from
$46
Chicago City Tour with Architecture River Cruise Option

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago with …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.8 (719)

Chicago City Tour with Architecture River Cruise Option

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago with...

2 to 4 hours • Free Cancellation
4.8 (719)
from
$50
Chicago River 90-Minute Architecture Boat Tour

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional …More

Chicago, USA
4.9 (1,876)

Chicago River 90-Minute Architecture Boat Tour

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional...

1 hour 30 minutes • Free Cancellation
4.9 (1,876)
from
$33
Chicago City Minibus Tour

Uncover the best of Chicago on an unforgettable highlights tour designed for travelers, sightseers, and history lovers alike! Step off the bus to admire Frank …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.9 (655)

Chicago City Minibus Tour

Uncover the best of Chicago on an unforgettable highlights tour designed for travelers, sightseers, and history lovers alike! Step off the bus to admire Frank...

2 hours • Free Cancellation
4.9 (655)
from
$50
Original Chicago Architecture Interiors Tour: Dazzling Interiors

UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper! There's only one company that's …More

Chicago, USA
5.0 (1,807)

Original Chicago Architecture Interiors Tour: Dazzling Interiors

UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper! There's only one company that's...

2 hours • Free Cancellation
5.0 (1,807)
from
$35
Chicago Architecture Tour: Underground Pedway and the Loop

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to …More

Chicago, USA
4.9 (563)

Chicago Architecture Tour: Underground Pedway and the Loop

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to...

2 hours • Free Cancellation
4.9 (563)
from
$35
Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour! Join the expert guides of Bobby’s Bike Hike, …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
5.0 (757)

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour! Join the expert guides of Bobby’s Bike Hike,...

4 hours 30 minutes • Free Cancellation
5.0 (757)
from
$89
Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings

Recently voted one of Cool Destinations's top food tours in the US. Discover the sweet side of the Windy City on the Underground Donut Tour, …More

Chicago, USA
5.0 (1,526)

Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings

Recently voted one of Cool Destinations's top food tours in the US. Discover the sweet side of the Windy City on the Underground Donut Tour,...

2 hours • Free Cancellation
5.0 (1,526)
from
$70
Bike Tour of Chicago's Lakefront Neighborhoods

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.9 (243)

Bike Tour of Chicago's Lakefront Neighborhoods

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence...

3 hours • Free Cancellation
4.9 (243)
from
$59
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
Chicago, USA
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
Chicago Family Food and Bike Tour with Top Attractions

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.9 (99)

Chicago Family Food and Bike Tour with Top Attractions

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past...

4 hours • Free Cancellation
4.9 (99)
from
$79
Chicago Pizza Tour

Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.9 (484)

Chicago Pizza Tour

Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the...

3 hours 30 minutes • Free Cancellation
4.9 (484)
from
$89
Chicago Landmarks and Museum Campus Small Group Segway Tour

Looking for fun things to do in Chicago? Explore the city with one of your professional guides on a scenic 6-7 mile tour. Begin your …More

Chicago, USA
5.0 (234)

Chicago Landmarks and Museum Campus Small Group Segway Tour

Looking for fun things to do in Chicago? Explore the city with one of your professional guides on a scenic 6-7 mile tour. Begin your...

2 hours • Free Cancellation
5.0 (234)
from
$70

Frequently Asked Questions

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

Recent tour reviews
Great Ride!!
New York City
Chicago River 90-Minute Architecture Tour
Carla_G, Oct 2026
Great Ride!!
I really enjoyed learning about the architecture in the City of Chicago. I highly recommend it!! If you go at night, dress accordingly.
Read more
Great tour guide!
New York City
Original Chicago Architecture Interiors Tour: Dazzling Interiors
650veroc, Sep 2026
Great tour guide!
Heath, the guide, helped make the tour very engaging with his considerable amount of knowledge and details about the subject of Chicago architecture. I highly recommend the tour!!
Read more
Highly recommend
New York City
Chicago River 90-Minute Architecture Boat Tour
Rachel_S, Sep 2026
Highly recommend
Had a blast! David was very knowledgeable and funny as heck! 10/10 highly recommend. 5 stars! Beautiful day
Read more
Wendella 90-minute Architecture Tour
New York City
Chicago River 90-Minute Architecture Tour
Larry_N, Sep 2026
Wendella 90-minute Architecture Tour
Everything was great. Very informative. The guide was fun and very knowledgeable. Everyone was civil. Great weather. All in all, a wonderful day. Wendella Tours has it together. Cons: No restrooms while waiting. "Go to Walgreens" does not cut it. Should be noted upfront. Once on the boat it was not an issue. No shade while waiting in line and two benches for seating are taken by those first in line. Otherwise be prepared to stand.
Read more
Exceeded our expectations
New York City
Original Chicago Architecture Interiors Tour: Dazzling Interiors
201ursulad, Sep 2026
Exceeded our expectations
Heath is a very knowledgeable guide. The buildings we visited were all spectacular and we saw as much as is possible within a 2-hour window. I highly recommend this tour as an introduction to Chicago’s architectural gems.
Read more
The best Architectural tour withHillary
New York City
Chicago River 90-Minute Architecture Boat Tour
939luellal, Sep 2026
The best Architectural tour withHillary
I loved this Architectural tour with Hillary Not only was she knowledgeable and funny but she brought something unique to the tour, not just speaking information, but it was the way she engaged us to really see and understand words attached to buildings so we would understand. Plus she has a great sense of humor. I enjoyed that. Would definitely go again and hopefully have her.
Read more
River Architecture Tour
New York City
Chicago Architecture River Cruise
rbarnes4, Sep 2026
River Architecture Tour
We took this tour on a recommendation and it did not disappoint! Sam đid a great job teaching us about the architecture of the buildings along the Chicago river! We would recommend this tour!
Read more
Happy customer
New York City
Chicago Pizza Tour
Paula_M, Sep 2026
Happy customer
If you want the BEST food tour in Chicago... this is the one!! Our tour guide..James was AMAZING! Very funny and knowledgeable. It was a plus riding on a bus and not walking for 3 hours. I felt extremely safe with our driver. The food was soooo good and learning some of the history of Chicago pizza was very interesting. Treat yourself to this tour when you're in the city. You'll be glad that you did!
Read more
Fantastic tour
New York City
Chicago Architecture Center River Cruise aboard First Lady
716dianed, Sep 2026
Fantastic tour
Wow! What a fabulous thing to do in beautiful Chicago. We loved every minute of it. Our tour guide was docent Mark and boy was he ever fantastic. He was sharp, knowledgeable, kind, passionate, professional, and witty. It was the highlight of our 3 day visit and we will be back.
Read more
Recommend This
New York City
Chicago Architecture Tour: Underground Pedway and the Loop
S9995FXannem, Sep 2026
Recommend This
Excellent! Such much info. So much fun. Heath was excellent !!!!
Read more
Wonderful experience!
New York City
Chicago City Tour with Architecture River Cruise Option
D9236FTsarahh, Sep 2026
Wonderful experience!
Haley, our driver/guide, was wonderful! She was very professional, courteous, knew her information, and was very enthusiastic. She was also a good driver! We would highly recommend this tour!
Read more
Enjoy a relaxing ride to watch the night skyline unfold.
New York City
Chicago Sightseeing River and Lake Cruise
Leslie_O, Sep 2026
Enjoy a relaxing ride to watch the night skyline unfold.
Just a very nice and informative tour and boat ride out on the lake and back. Trip length was very good. Everything advertised about the tour was fulfilled. Tour guide was well informed and courteous. Staff on board were also very attentive.
Read more
Exceeded my expectations!!
New York City
Chicago Architecture Center River Cruise aboard First Lady
paulquinng, Sep 2026
Exceeded my expectations!!
Having grown up in the Chicago area over 50yrs ago, I finally decided to take this well known architectural river cruise with First Lady. It did not disappoint, and surpassed any expectations I may have had.Our docent (guide), Bob P was a wealth of knowledge, and I was truly amazed as to how he remembered so many dates, architectural firms, addresses, and history about each building!! AND he’s a volunteer!!I highly recommend this tour for anyone, and we had a beautiful fall day with perfect sunny weather to enjoy it!
Read more
🤞wonderful
New York City
Chicago City Minibus Tour
Antoinette_C, Sep 2026
🤞wonderful
Great experience loved the guide Haley and her knowledge and ability to put up with annoying tourist.
Read more
Chicago Architectural Tour (so original)
New York City
Chicago Architecture River Cruise
Elizabeth_J, Sep 2026
Chicago Architectural Tour (so original)
Boat trip was great, totally lucked out with the weather, crew was wonderful. Tour guide was a bit much.
Read more
Terrific tour of Chicago
New York City
Chicago City Tour with Architecture River Cruise Option
Vickie_H, Sep 2026
Terrific tour of Chicago
This city tour was terrific! Our guide, Avery, was very informative and shared highlights of Chicago's history. He packed a lot of great stories into our tour. We thoroughly enjoyed it.
Read more
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