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Top Chicago City Tours

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Chicago 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
4.8 (10,806)

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 (10,806)
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
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
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

4.9 (16,509)

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 (16,509)
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

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 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
4.7 (1,581)

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 (1,581)
from
$45
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

4.6 (892)

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 (892)
from
$34
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

4.8 (700)

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 (700)
from
$46
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

4.9 (1,874)

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 (1,874)
from
$33
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

4.8 (716)

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 (716)
from
$50
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
4.9 (654)

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 (654)
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

5.0 (1,805)

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 (1,805)
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

Likely to Sell Out
Likely to Sell Out
4.9 (562)

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 (562)
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
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

5.0 (1,525)

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 (1,525)
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
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
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
4.9 (483)

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 (483)
from
$89
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
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
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 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

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 Tour Guide
New York City
Chicago River 90-Minute Architecture Boat Tour
Adam_Y, Sep 2026
Great Tour Guide
The tour guide, Adam was personable, knowledgeable, funny, patient and engaging. I highly recommend this tour!
Read more
Amazing tour.
New York City
Original Chicago Architecture Interiors Tour: Dazzling Interiors
bpnixon1, Sep 2026
Amazing tour.
Do it. One of the best I’ve ever been on. Great time for everyone. Absolutely amazing. Guide was awesome and very knowledgeable and so easy going. Definitely recommend
Read more
This was an awesome tour!...
New York City
Chicago River 90-Minute Architecture Tour
Jenae_D, Sep 2026
This was an awesome tour!...
This was an awesome tour! They were on time, kind and had in board drinks and bathroom. Would def recommend!
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
Touring Chicago
New York City
Chicago River 90-Minute Architecture Tour
Howell_B, Sep 2026
Touring Chicago
This tour was excellent. The guide was knowledgeable. The experience was great. This was the easiest and quickest way to see the city.
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
Architecture in Chicago is worthy.
New York City
Chicago River 90-Minute Architecture Boat Tour
Joanne_J, Sep 2026
Architecture in Chicago is worthy.
The Architecture tours on the Chicago River are wonderful. Hillary our guide was knowledgeable and funny and good at her job.
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
Chicago history as told through stunning architecture
New York City
Original Chicago Architecture Interiors Tour: Dazzling Interiors
dizzycow1, Sep 2026
Chicago history as told through stunning architecture
A fascinating tour of some spots I would have never thought to check out on my own. The guide was incredibly knowledgeable and engaging, and his love for the city was apparent. He even managed to keep my eight-year-old interested throughout. A good mix of outdoor and indoor settings, with plenty of rest spots, very manageable even for those who aren't big on walking. A great way to take in Chicago history.
Read more
Great
New York City
Chicago Architecture River Cruise
armandomR3132LF, Sep 2026
Great
Great river boat ride and the crew are very friendly
Read more
This is the one
New York City
Lake Michigan Sunset Cruise in Chicago
Relax40375478039, Sep 2026
This is the one
This was great! Since the sunsets earlier in September we got to see the city lit up. This is the cruise to go on
Read more
Wonderful experience
New York City
Chicago Architecture River Cruise
G5960HBjulieb, Sep 2026
Wonderful experience
Great time. Sam s was a super entertaining and knowledgeable guide for the tour.
Read more
Beautiful night in downtown Chicago
New York City
Chicago River 45-Minute Architecture Tour from Magnificent Mile
Robert_C, Sep 2026
Beautiful night in downtown Chicago
My girlfriend and I spent a day in Chicago on her birthday! One of the excursions that I booked for us was this cruise. It was totally awesome!
Read more
Don’t miss it
New York City
Chicago River 45-Minute Architecture Tour from Magnificent Mile
749allanl, Sep 2026
Don’t miss it
Don’t miss it, exceptional tour with a very knowledgable and engaging tour guide. Great experience and a must do.
Read more
Sunset cruising the night away
New York City
Lake Michigan Sunset Cruise in Chicago
Angela_S, Sep 2026
Sunset cruising the night away
Beautiful views of the skyline and great music made our evening! The host provided some interesting commentary and history about Chicago, but didn’t talk the whole time so we were also able to enjoy our own conversation. We arrived about 25 minutes before the boat was scheduled to leave and there were a ton of people lined up. Seating is first-come, first-serve, so arrive earlier if you want to get prime seating on deck near the edge or back of the boat for the best photo ops. The back will give you the skyline as the boat drives out of the city onto Lake Michigan. Either side will give photo ops as the boat drives up and down Lake Michigan a couple times each after dusk. People move around a lot, so you can still get good photos no matter where you sit, you may just have a bunch of people in your photos. This was a great experience!
Read more
A great way to see downtown Chicago from the river and the skyline from Lake Michigan
New York City
Chicago Sightseeing River and Lake Cruise
Michele_B, Sep 2026
A great way to see downtown Chicago from the river and the skyline from Lake Michigan
Informative guide and a great small trip with plenty to see. Good facilities on board and good weather was a bonus!
Read more
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