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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 experiences in Chicago

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 4.6 out of 5 from 242 ratings.From $112.10
Chicago River cruise boat at night with city skyline in the background.
Chicago at Night: River & Lake Sightseeing Cruise by First Lady
Sightseeing Cruises
from
$50
Chicago at Night: River & Lake Sightseeing Cruise by First Lady. Rated 4.5 out of 5 from 11 ratings.From $50
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 4.8 out of 5 from 53 ratings.From $45
Free cancellation
Guests enjoying drinks on a Lake Michigan dinner cruise with Chicago skyline in the background.
Lake Michigan Dinner Cruise
Dinner Cruises
from
$112.10
Lake Michigan Dinner Cruise. Rated 4.7 out of 5 from 48 ratings.From $112.10

What our guests say

Floretta P

United States
Couple
May 2026

+1 more

The staff is friendly and very nice. Wedding Anniversary and Husband birthday. As for me 14 yrs if chemotherapy enjoying life.

Chicago Dinner Cruise

Nakisha A

United States
Couple
May 2026
I absolutely loved the view, the food, and the drinks...everyone was so friendly and welcoming...I've never had dinner on the water so that was definitely a great experience, I took my fiancé for his bday and he never been there so that was great seeing his face and how much he loved it 🥰

Chicago Dinner Cruise

Shatavia B

United States
Couple
May 2026
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

Chicago Dinner Cruise

Jessica S

United States
Couple
Apr 2026
My husband and I celebrated our 1 year wedding anniversary on the odyssey boat and we had an amazing time. From the time we got on the boat everyone was so friendly and the atmosphere was amazing. We took pictures outside and after dinner we danced the night away. It was a first time for both of us and we will definitely be back to do it again. I would like to say thank you to the staff and dj for making our special day even more special. Can't wait to do it again.

Chicago Dinner Cruise

Tanisha H

United States
Couple
Apr 2026

+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.

Chicago Dinner Cruise

Gomes L

Group
May 2026
Only a cruise like this one lets you take such beautiful photos of Chicago at night. Beyond the cruise itself, there was a great atmosphere on board thanks to the wonderful crew. I highly recommend it!

90-min Scenic Sunset Lake Michigan Cruise by Wendella

Justin B

Solo
May 2026
Honestly the cruise was great but the guide Scotty D was incredible. He was fun, knowledgeable, and engaging. The cruise was a good mix of architecture and lake views, timely, and comfortable.

90-min Scenic Sunset Lake Michigan Cruise by Wendella

Gabriela S

United States
Group
May 2026
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