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Discover the best things to do in Chicago

A curated collection of the city’s top-rated tours, iconic attractions, and unmissable things to do.
Discover the best things to do in Chicago

Top experiences in Chicago

Free cancellation
Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
90-min Chicago River Architecture Cruise by Wendella
Sightseeing Cruises
$45
90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 459 ratings.From $45
Free cancellation
Dinner cruise boat on Chicago River with illuminated city skyline at night.
Chicago Dinner Cruise
Dinner Cruises
from
$112.10
Chicago Dinner Cruise. Rated 4.5 out of 5 from 111 ratings.From $112.10
Free cancellation
Chicago River cruise boat passing under a bridge with city skyline.
45-min Chicago River Architecture Cruise by Wendella
Sightseeing Cruises
from
$28
45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 718 ratings.From $28
Free cancellation
Tour boat on Chicago River with city skyline in background.
Chicago River Architecture Cruise
Sightseeing Cruises
from
$28
Chicago River Architecture Cruise. Rated 4.9 out of 5 from 718 ratings.From $28
Cruise boat on Chicago River passing under Clark Street Bridge.
Official Chicago Architecture Cruise by First Lady
Sightseeing Cruises
$57
Official Chicago Architecture Cruise by First Lady. Rated 4.9 out of 5 from 120 ratings.From $57
Free cancellation
Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
Odyssey Lake Michigan Dinner Cruise
Dinner Cruises
from
$132.58
Odyssey Lake Michigan Dinner Cruise. Rated 4.6 out of 5 from 47 ratings.From $132.58
Free cancellation
Guests dining on a Chicago dinner cruise with city skyline views through glass windows.
Chicago Lunch Cruise
Lunch Cruises
from
$62.88
Chicago Lunch Cruise. Rated 1 out of 5 from 1 ratings.From $62.88
Free cancellation
Chicago River architecture cruise boat passing under a lift bridge with city skyscrapers in the background.
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella
Sightseeing Cruises
$45
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.7 out of 5 from 76 ratings.From $45
Free cancellation
Cruise boat on Lake Michigan with Chicago skyline at sunset.
90-min Scenic Sunset Lake Michigan Cruise by Wendella
Sightseeing Cruises
$45
90-min Scenic Sunset Lake Michigan Cruise by Wendella. Rated 4.9 out of 5 from 25 ratings.From $45
Tour boat on Chicago River with city skyline and bridge in background.
75-Minute Chicago River Architecture Cruise by Shoreline
Sightseeing Cruises
from
$39
75-Minute Chicago River Architecture Cruise by Shoreline. Rated 4.4 out of 5 from 101 ratings.From $39
View from the Skydeck at Willis Tower, Chicago, overlooking the cityscape.
Skydeck Chicago Tickets
Willis Tower Skydeck Tickets
from
$42.33
Skydeck Chicago Tickets. Rated 4.7 out of 5 from 127 ratings.From $42.33
Free cancellation
Moored tour boats on the Chicago River at sunrise with city skyline.
Chicago Architecture Evening Cruise by Shoreline
Sightseeing Cruises
from
$46
Chicago Architecture Evening Cruise by Shoreline. Rated 4.9 out of 5 from 28 ratings.From $46

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We research and organise all unique experiences - from tickets to tours to special combos - so you get all the choices without the clutter.

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Every supplier is vetted for quality, reliability, and value so you only get top rated experiences. No surprises, no disappointments.

All the best options, in one place

Each experience is thoughtfully organised to give you maximum availability, great value and an easy way to choose.

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We curate the best ways to experience
We partner with the best
All the best options, in one place
Book with complete peace of mind

Must do things in Chicago

Big Bus Chicago Hop-on Hop-off Tours

1Big Bus Chicago Hop-on Hop-off Tours

Experience Chicago like never before with a Big Bus tour. Marvel at architectural wonders like the Willis Tower, explore cultural gems at Millennium Park and soak in stunning skyline views from Navy Pier. Get a combo ticket to the 360 Chicago Observatory and make the best of your stay in the city.
360 Chicago

2360 Chicago

Discover Chicago's skyline in all its glory at 360 Observation Deck! Marvel at iconic landmarks, like Willis Tower and Lake Michigan, and witness the city's architectural wonders and breathtaking sunset views.
Chicago River Architecture Cruise Tickets

3Chicago River Architecture Cruise Tickets

The Chicago Architecture Foundation Center River Cruise follows the Chicago River through the Loop and along the lake, with licensed architect guides pointing out the city's landmark skyscrapers and design history. Find 90-minute standard cruise tickets, sunset session options, and evening cruise formats here.
Willis Tower Skydeck Tickets

4Willis Tower Skydeck Tickets

Embark on an exhilarating adventure as you stand on the Skydeck's breathtaking glass ledge, suspended 1,353 feet above the vibrant city of Chicago. Ensure your spot by securing tickets that grant you exclusive access to this awe-inspiring experience.

What our guests say

Anuj M

Canada
Couple
4 days ago

+4 more

That's absolutely great experience with Wendella Tours & Cruises. They've explained very well throughout the ride. Thank you for making our trip remarkable.

45-min Chicago River Architecture Cruise by Wendella

Matias S

Argentina
Solo
6 days ago
The great exposition of yours tourist guide, amazing, funny and very interesting. The length was perfect and the places incredibles. A must do in Chicago.

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella

Gabriela S

United States
Group
Last week
Without a doubt, one of my best experiences. I would take this cruise again and again. We were absolutely delighted—they even wished my sister a happy birthday over the PA system. They made us feel so special. The food was delicious, and we could eat as much as we wanted of everything included, right down to dessert. We don’t speak English, but the staff did their best to make sure we understood everything. They even took a souvenir photo of us—I loved it ❤️ If you visit the area, taking this cruise is the best thing you can do ❤️❤️

Lake Michigan Dinner Cruise

Shatavia B

United States
Couple
Last week
It certainly was really nice experience but I do think that for the quality and amount of food the cruise is a little Expensive and should be alot more selection for people who have allergies to certain foods other than that very nice

Odyssey Lake Michigan Dinner Cruise

Tara V

United States
Couple
2 weeks ago
Kenny the tour guide was very knowledgeable and kept us entertained! The history of the architecture was fascinating to learn about.

90-min Chicago River Architecture Cruise by Wendella

Tanisha H

United States
Couple
2 weeks ago

+4 more

Cruising down the river and looking up at spots like the Wrigley Building and Willis Tower just hit different from the water. You really see the details, the mix of old-school and modern, and how everything fits together. But the best part? The vibe. It’s calm, a little breezy, the city reflecting off the water… and you lowkey feel like you seeing Chicago from a whole new angle—even if you’ve lived here your whole life. If I had to sum it up real simple: It felt like a history lesson, a skyline view, and a peaceful reset all in one.

Odyssey Chicago River Architecture Dinner Cruise

Marlene W

United States
Couple
2 weeks ago
Anyone who visits Chicago should definietly take this cruise. What a beautiful city and the diversivied architure is spectacular. Our guide gave us a detailed history of so many of the buildings. He was amazing and it was fasinating to hear what a transformation Chicago and the Chicago went through, from dead livestock to a beautiful river and riverwalk. 5 star recommendation!

Official Chicago Architecture Cruise by First Lady

Sarantuya B

United States
Group
Apr 2026
We just came from Mongolia. Visit the skydeck. We did very enjoyed our time there . It's beautiful place i would love the place. We have small businesses in our country, we did beautiful pictures for our business product. Thankyou Chicago!

Skydeck Chicago Tickets

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