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Chicago, United States

Chicago for luxe lovers

Discover Chicago in style! Indulge in our collection of luxury experiences and bespoke tours, tailored for discerning explorers like you.
Couple relaxing on a yacht at sunset with cocktails, ideal for luxury travelers.

Top things to do

Top experiences in Chicago

What our guests say

Paul M

United States
Couple
Last week

+2 more

Food was great...atmosphere was great, music was great....and the staff was very welcoming...i will do this again!!! Cannot beat the views of they city!!

Chicago Dinner Cruise

Howard W

United States
Couple
Aug 2026
I loved it. 10 out of 10! The staff very professional. The DJ was ok and the food was delicious. We had a window seat which made our experience incredible. The View was amazing. Highly recommend.

Chicago Dinner Cruise

Gianna B

United States
Couple
Jul 2026
PHENOMENAL!! And legit! Such an amazing experience, amazing food, SO romantic, staff and DJ were very kind! It honestly felt too good to be true at some moments, but it was an amazing experience and I would definitely do it again!

Chicago Dinner Cruise

Eric H

United States
Couple
Jul 2026
What I enjoy about the cruise was the DJ and the nice people working on the cruise me and my wife will definitely be back!!!

Chicago Dinner Cruise

Louise H

United States
Solo
Jul 2026

+2 more

Our evening on the Odyssey Chicago River Architecture Dinner Cruise was unforgettable. The views of Chicago’s iconic skyline and historic buildings were breathtaking, and the narration made the city’s architecture come alive. The staff was genuinely warm and attentive, the meal was delicious, and the atmosphere on board felt both elegant and relaxed. Watching the city lights reflect on the river while enjoying dinner with friends was a perfect experience. I would gladly recommend this cruise to anyone looking for a memorable way to experience Chicago.

Chicago Dinner Cruise

Vanessa W

United States
Couple
Jul 2026

+1 more

Overall, the boat cruise was a great experience\. The food was delicious, the staff was friendly and attentive, and the scenery and atmosphere were beautiful\. Everything was set up nicely and had the potential to be an amazing time\. Unfortunately, the DJ completely ruined the vibe\. The music selection was terrible, there was no energy, and it never got the crowd engaged\. On a cruise like this, the DJ really sets the tone for the entire experience, and this one missed the mark\. If the cruise gets a new DJ, I would definitely recommend it\. Everything else was great, but the entertainment needs a major upgrade\.

Lake Michigan Dinner Cruise

Cristina K

United States
Couple
Jul 2026

+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.

90-min Scenic Sunset Lake Michigan Cruise by Wendella

Shannon H

Couple
Jul 2026
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