Chicago for first-timers
Welcome to Chicago! Dive into the city's vibrant culture and explore must-see attractions. Our expertly curated tours will ensure you make the most of your inaugural visit.

Top things to do
Slide 1 of 6
Top experiences in Chicago
Free cancellation
Slide 1 of 1, Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.

Free cancellation
Slide 1 of 1, Chicago River cruise boat passing under a bridge with city skyline.

Slide 1 of 1, View from the Skydeck at Willis Tower, Chicago, overlooking the cityscape.

Free cancellation
Slide 1 of 1, Chicago River architecture cruise boat passing under a lift bridge with city skyscrapers in the background.

4.8(198)
Sightseeing Cruises
$45
Slide 1 of 1, Chicago River cruise boat at night with city skyline in the background.

Free cancellation
Slide 1 of 1, Family enjoying view from Chicago 360 Observation Deck with city skyline.

Slide 1 of 1, Chicago River cruise with tourists viewing downtown skyscrapers.

Free cancellation
Slide 1 of 1, Tour boat on Chicago River with city skyscrapers in the background.

Free cancellation
Slide 1 of 1, Guided group walking under Calder's Flamingo sculpture in Chicago.

Free cancellation
Slide 1 of 1, Guest viewing Chicago skyline from lakefront during Skydeck and Architecture Cruise tour.

What our guests say
V
Valerie K
United StatesGroup
5/5
Tess was our guide and she was wonderful! Very informative and you can tell she loves what she does. The crew was professional and we had a wonderful smooth ride!
90-min Chicago River Architecture Cruise by Wendella
C
Cristina K
United StatesCouple
5/5
+1 more
It was a great easy ride around the city thanks to the captain. We liked how you timed the cruise so people could see the sunset just in time. Boarding was easy. The guide was informative but not intrusive in letting people enjoy the view to the nice music. It was a very pleasant experience and I will recommend to anyone I know who is visiting Chicago. It was truly the highlight of my visit.
Lake Michigan Cruise
L
Lydia U
United StatesCouple
5/5
This tour covered a lot more buildings than I though it would, it felt as though the guide had something to say about nearly every building we passed. For 45 minutes, the guide, who did speak pretty quickly, was able to fit in so much information! I also appreciate the sense of humor with which the tour was given; this and other factors made it so that you didn't at any point feel like you were being lectured at and want to zone out. I was engaged the whole time. One of the best parts was heading closer to the mouth of the river and being shown such a scenic view of the city, this was beautiful! Though I would consider doing a longer cruise because I would have loved to learn more, this is very worthwhile in and of itself and especially if you only have (exactly) 45 minutes.
45-min Chicago River Architecture Cruise by Wendella
J
Jill C
Couple
5/5
The views of the city from the water, learning about the architecture, fun facts, the tour guide very good. hot but interesting day!
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella
S
Shannon H
Couple
5/5
The guide was amazing! He was very funny while being so informative and never crass. The sunset tour was beautiful and I thought it was very smart to offer sweatshirts in the lovely cabin. The bar staff was slammed but still so nice! Would definitely recommend to Chicago natives and out of towners!
Chicago at Night: River & Lake Sightseeing Cruise by First Lady
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Anggie C
EcuadorCouple
5/5
It's so easy to shop online, and the app is very user-friendly. I really liked that it shows you photos of all the available tour options, so you know exactly what you'll be doing! Highly recommended
Skydeck Chicago Tickets
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Henry L
United StatesCouple
5/5
The. Views were incredible and the atmosphere delightful. Our bartender was very attentive and helpful. We never felt rushed only relaxing vibes.
360 Chicago Sip & View
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