Dinner Cruises

Chicago Dinner Cruise

Duration

2 hr - 3 hr

Free cancellation

Free cancellation up to 24 hours before the start of your experience

Book now, pay later

Book now without paying anything. Cancel for free if your plans change.

Meals included

Indulge in a sumptuous meal as a part of your experience

4.7/5

(23)

Brendon H

Couple

Verified booking

Last week

It was a great experience. I've seen other reviews on Google bashing the food and I don't agree! The venue is gorgeous, the wait staff are so attentive and excellent, the scenery is amazing! It was such a great experience and the other clientele on the boat was such a diverse group. It was beautiful and such a great way to celebrate a birthday! Highly recommend!

Kennedy F

Couple

Verified booking

Feb 2026

The Odyssey was 10/10. Our waitress Nikki was 10/10 she gave the run down on everything on the menu. Drinks were good , the DJ played every kind of music for everybody to dance too. All around it was relaxing and the views were out of this world. Would I go back of course.

Charlotte M

Couple

Verified booking

Mar 2026

The atmosphere was amazing. My husband and I were on vacation for my birthday and this cruise was the highlight of my trip. The staff and captain were amazing and the food was delicious. There was nothing better than the views, they were breathtaking!

Julian V

Family

Verified booking

4 days ago

Everything was great—from the music and the views to the food. It was a perfect, unforgettable experience, ideal for celebrating birthdays or graduations. The views of the architecture were perfect; it was the perfect plan.

Destiny M

Couple

Verified booking

3 days ago

Views were incredible, food was good , vibes were there , wasn't a rocky ride would highly recommend for date night & quality time spent with your significant other

Fely C

Couple

Verified booking

Feb 2026

Very romantic, a lot of good options for appetizers, entrees and desserts. Not to mention their drink menus were excellent! Loved this experience with my husband.

Enjoy a 2.5-hour cruise on the Chicago River and Lake Michigan with a gourmet dinner and live entertainment onboard.

Relax in a climate-controlled interior deck while enjoying scenic views of Chicago’s skyline and architecture.

Enjoy a chef-prepared meal as you take in the breathtaking views of Chicago's skyline and iconic architecture.

Live curated entertainment, along with an onboard bar with beverages available for purchase, enhances your dining experience, making it perfect for special occasions.

Choose between a Chicago River cruise with a plated gourmet dinner, a Lake Michigan cruise with a plated gourmet dinner, or a Lake Michigan cruise with a buffet dinner.

2.5-hour sightseeing and dinner cruise on the Chicago River and Lake Michigan

Plated gourmet dinner with modern American cuisine (Menu) (as per option selected)

Plated 3-course dinner with contemporary American cuisine (Menu) (as per option selected)

Buffet dinner with global fusion cuisine (Menu) (as per option selected)

Sightseeing and twilight views of the Chicago skyline

Live onboard entertainment

Climate-controlled interior deck

Accommodation for dietary restrictions to the best of the crew's ability

Onboard bar with cocktails, wine, and beer (available for purchase)

Alcoholic beverages (available for purchase onboard)

Transportation to/from the departure location

Additional purchases onboard not included in your ticket

TOTAL DURATION3 hours - 3 hours
MODE OF TRANSFERCruise Ship
1 Boarding point
Chicago River Esplanade
Sights covered
Tribune Tower
Wrigley Building
Merchandise Mart
Civic Opera House
Willis Tower
Wolf Point
Marina City
DuSable Bridge
Aon Center
Trump International Tower
Navy Pier
TOTAL DURATION2 hours 30 minutes - 3 hours
MODE OF TRANSFERCruise Ship
1 Boarding point
Navy Pier
Get direction
Sights covered
Chicago Harbor Lighthouse
Willis Tower
John Hancock Center
Aqua Tower
The St. Regis Chicago
Marina City
Lake Point Tower
Harbor Point
340 on the Park
Adler Planetarium
Soldier Field
Shedd Aquarium
Fireworks display
TOTAL DURATION2 hours - 3 hours
MODE OF TRANSFERCruise Ship
1 Boarding point
Navy Pier
Get direction
Sights covered
Willis Tower
John Hancock Center
Aon Center
Shedd Aquarium
Field Museum
Adler Planetarium
Soldier Field
Buckingham Fountain
Grant Park
Marina City
Wrigley Building
Tribune Tower
Chicago Harbor

You can cancel these tickets up to 24 hours before the experience begins and get a full refund.

23 reviews
How do we collect reviews?
These ratings include verified reviews from both Headout guests and our trusted partners who operate this experience locally. All reviews come from real travelers who've taken this experience.
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What our guests say
Brendon H
Couple
Verified booking
Last week
It was a great experience. I've seen other reviews on Google bashing the food and I don't agree! The venue is gorgeous, the wait staff are so attentive and excellent, the scenery is amazing! It was such a great experience and the other clientele on the boat was such a diverse group. It was beautiful and such a great way to celebrate a birthday! Highly recommend!
Charlotte M
Couple
Verified booking
Mar 2026
The atmosphere was amazing. My husband and I were on vacation for my birthday and this cruise was the highlight of my trip. The staff and captain were amazing and the food was delicious. There was nothing better than the views, they were breathtaking!
Julian V
Family
Verified booking
4 days ago
Everything was great—from the music and the views to the food. It was a perfect, unforgettable experience, ideal for celebrating birthdays or graduations. The views of the architecture were perfect; it was the perfect plan.
Destiny M
Couple
Verified booking
3 days ago
Views were incredible, food was good , vibes were there , wasn't a rocky ride would highly recommend for date night & quality time spent with your significant other
Caleb O
Couple
Verified booking
3 days ago
Amazing sights with excellent food and service! Wesley was so attentive, had incredible recommendations and even braved the cold to take the best photos of us!

What to bring

A valid ID is required for guests aged 21 and above to access the onboard bar.

It’s recommended to carry a light jacket or wrap, as the open-air deck can get breezy.

What's not allowed

Bringing outside food or beverages on board is not permitted.

Weapons of any kind are strictly prohibited on the cruise.

Additional information

Boarding begins 30 minutes prior to departure from Monday to Saturday, and 45 minutes before departure on Sundays.

Guests should arrive at least 45 minutes early for check-in and boarding, and allow an additional 30 minutes for parking and reaching the boarding location.

Cruise timings may vary, so refer to the cruise calendar and your email confirmation for the most accurate schedule.

This is a seasonal experience and may be affected by weather conditions.

Menu offerings are subject to change depending on seasonal availability.

Your voucher will be emailed to you shortly.

Display the voucher on your mobile phone with a valid photo ID at the starting point.

Please check your final voucher for the starting point details & specific instructions.