Dinner Cruises

Chicago Dinner Cruise

4.6/5(427)

Sandra F

Group

Verified booking

5 days ago

The most enjoyable part of the dinner cruise was the beautiful views, the relaxing atmosphere, and celebrating my mom’s birthday. What made the evening especially special was how the staff went out of their way to make her feel appreciated. Several staff members came over to wish her a happy birthday, and it genuinely made her so happy. Their kindness and thoughtfulness made the experience even more memorable for our family.

Ashley T

Couple

Verified booking

2 days ago

I really enjoyed the views and the different environments on each level that you can experience after dinner. Seeing the views from the top level was beautiful.

Latonya B

Couple

Verified booking

3 weeks ago

The Chicago Dinner Cruise was the perfect way to end celebrating our anniversary!!! Everything was nice. I did have to retrieve my tickets from the ticket box, but that was nothing. Once we got on the boat everything was so pretty and neat. We were escorted to our table and had the best waitress named Lauren. She gave her recommendation when asked and they did not fail. She recommended the Salmon and it was great!! Actually all of the food was great and well seasoned. The view outside of the boat was everything. We were celebrating our anniversary so the DJ came around and got our first dance song and when he played it we went to the dance floor and dance and was recognized!! So sweet!! This experience was definitely a 10 out of 10 highly recommend.

Banquetta F

Solo

Verified booking

3 weeks ago

I was nervous waiting in line as I overheard a worker on the oddyssey say "we always have problems with people who purchase on headout" However, I did not encounter any problems whe retrieving my ticket. The staff was really nice and attentive. The Dj was the highlight for me. He played a good mix of music. The food was good but nothing to write home about. The weather was good so it made for a smooth, calming ride. I would recommend

Stephanie H

Couple

Verified booking

3 weeks ago

Wonderful dinner cruise! Thank you to Dina and Angelica who made my birthday cruise truly magical. Seating for dinner was a little tight but once we disembarked we requested for window seating and lucky enough to make the waitlist and was definitely worth it the view. The top deck was vape and smoking friendly so we enjoyed our drinks while watching the sun set. We will most definitely sailing again with the Oddessy crew.

Eleonora L

Couple

Verified booking

Aug 2026

Everything was absolutely perfect! The onboard staff were incredibly kind and welcoming, and our waiter, Adam, was attentive, friendly, and always happy to help. The food, the organization, and the table they gave us right by the window were all wonderful. The view was amazing, and we were also lucky enough to have perfect weather. Everything was simply perfect from start to finish. Highly recommended!

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.

427 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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Guests from Mexico, Canada, United Kingdom and over 12 countries have loved this experience
What our guests say
Banquetta F
Solo
Verified booking
3 weeks ago
I was nervous waiting in line as I overheard a worker on the oddyssey say "we always have problems with people who purchase on headout" However, I did not encounter any problems whe retrieving my ticket. The staff was really nice and attentive. The Dj was the highlight for me. He played a good mix of music. The food was good but nothing to write home about. The weather was good so it made for a smooth, calming ride. I would recommend
Stephanie H
Couple
Verified booking
3 weeks ago
Wonderful dinner cruise! Thank you to Dina and Angelica who made my birthday cruise truly magical. Seating for dinner was a little tight but once we disembarked we requested for window seating and lucky enough to make the waitlist and was definitely worth it the view. The top deck was vape and smoking friendly so we enjoyed our drinks while watching the sun set. We will most definitely sailing again with the Oddessy crew.
Twanna J
Couple
Verified booking
3 weeks ago
The great host service the food and the fun atomsphere.the dj and music was alsome. I really enjoyed myself it was my first time on the dinner cruise and o planned on going again. Thanks for great night out
Howard W
Couple
Verified booking
3 weeks ago
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.
Ashley B
Couple
Verified booking
3 weeks ago
i i enjoyed the atmosphere. it was calm and romantic, it was an amazing experience. it was the best date/half anniversary we could have. we are going to add this experience to once a year

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.