Headout logo. Link to home.

Help

Sell on Headout

Top experiences in Chicago

5 experiences

Free cancellation
Dinner cruise boat on Chicago River with illuminated city skyline at night.
Chicago Dinner Cruise
Cruises
from
$112.10
Chicago Dinner Cruise. Rated 4.6 out of 5 from 162 ratings.From $112.10
Free cancellation
Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
Odyssey Lake Michigan Dinner Cruise
Cruises
from
$132.58
Odyssey Lake Michigan Dinner Cruise. Rated 4.6 out of 5 from 81 ratings.From $132.58
Free cancellation
Odyssey Chicago River boat cruising on the Chicago River with city skyline.
Odyssey Chicago River Architecture Dinner Cruise
Cruises
from
$139.42
Odyssey Chicago River Architecture Dinner Cruise. Rated 4.6 out of 5 from 47 ratings.From $139.42
Free cancellation
Chicago River with tour boats and bridges in downtown Chicago.
Sea Dog Cruise on Lake Michigan
Cruises
from
$35.72
Sea Dog Cruise on Lake Michigan. Rated 5 out of 5 from 2 ratings.From $35.72
Free cancellation
Guests enjoying drinks on a Lake Michigan dinner cruise with Chicago skyline in the background.
Lake Michigan Dinner Cruise
Cruises
from
$112.10
Lake Michigan Dinner Cruise. Rated 4.6 out of 5 from 34 ratings.From $112.10

How Headout makes choosing experiences effortless

We curate the best ways to experience

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

We partner with the best

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.

Book with complete peace of mind

Free cancellations, Flexible payments, and 24/7 support - thoughtfully designed for flexibility, assurance, and total peace of mind.

1/4

Slide 1 of 4
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
Download app section background

What our guests say

Floretta P

United States
Couple
Last week

+1 more

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

Odyssey Lake Michigan 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

Odyssey Lake Michigan Dinner Cruise

Nakisha A

United States
Couple
2 weeks ago
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 🥰

Odyssey Chicago River Architecture 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.

Odyssey Chicago River Architecture Dinner Cruise

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

Josiah C

United States
Couple
3 days ago
My wife and I first time we did something like this it was definitely fun food was good could be better but overall it was fun definitely a repeat experience

Chicago Dinner Cruise

Noofil M

United States
Couple
Last week
It was an amazing experience. We went to celebrate our wedding anniversary and the server made our evening special with constant attention. I would highly recommend.

Chicago Dinner Cruise

We've served 51 million+ guests and we are here for you

51 million+

Happy customers across 10,000+ experiences

In the media

Featured and recommended by the best brands

24 x 7 help center

Have a question? Live chat with local experts anywhere, anytime