Dinner Cruises

Chicago Dinner Cruise

Duration

2 hrs - 3 hrs

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

4.6/5(313)

Terry L

Couple

Verified booking

Last week

My daughter and I take a mother 's / daughter's vacy( to various cities) each year trip to celebrate her July 17 birthday. This year was no exception. We chose Chicago as our destination. As we walk around Michigan Ave making several stops, A T ( my daughter ) felt insecure and depressed. She felt that people were looking at her in a negative way. She was born with a facial palsy . Over the years, it has gotten more apparent. Currently she hides behind a mask. Once, we board the ship, her dispostion changed. The people were friendly, food was very tasty, and the music was great ! Shout out to the DJ. The best part of the cruise was Ramsey ! The manager! He was so efficient. He boost my daughter ego and made her feel so much better about her self. He even help encouraged her to get on the dance floor! It was great !

Debonne W

Solo

Verified booking

2 weeks ago

I have wanted to do this cruise since December 2022. Odyssey Dinner Cruise offers a combination of amazing experiences for the solo, paired, or group travelers. From start to finish, the respect and courtesy are refreshingly exceptional. Thank you! Cruising along stretches of the Chicago River while viewing the city's impeccable architecture and ongoing construction projects makes it a high spirited trip. The cuisine and the time of serving the sumptuous food and beverages are well-organized. The musical selections and the deejay makes you groove and stomp your feet. I met new folks and had a wonderful exchange with them. Cruising with Odyssey is cruising in excellence and it is reasonably priced.

Louise H

Solo

Verified booking

2 weeks ago

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.

Jamille C

Couple

Verified booking

2 weeks ago

The cruise was phenomenal. The food was great ,the views were amazing and the dj was just super. He came to our table and talked to us prior to us shipping off and of course we told him we were celebrating our anniversary and he gave us a shout out and played our favorite love song " LOVE BALLAD" by LTD. It was special and so beautiful, I would highly recommend. A must do when visiting Chicago 👍🏾🔥

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
TOTAL DURATION2 hours 30 minutes - 3 hours
MODE OF TRANSFERCruise Ship
1 Boarding point
Navy Pier
Get direction
Sights covered
Chicago Harbor Lighthouse
TOTAL DURATION2 hours - 3 hours
MODE OF TRANSFERCruise Ship
1 Boarding point
Navy Pier
Get direction
Sights covered
Willis Tower

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

313 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.
246
33
22
6
6
Guests from Mexico, United Kingdom, Canada and over 9 countries have loved this experience
What our guests say
Debonne W
Solo
Verified booking
2 weeks ago
I have wanted to do this cruise since December 2022. Odyssey Dinner Cruise offers a combination of amazing experiences for the solo, paired, or group travelers. From start to finish, the respect and courtesy are refreshingly exceptional. Thank you! Cruising along stretches of the Chicago River while viewing the city's impeccable architecture and ongoing construction projects makes it a high spirited trip. The cuisine and the time of serving the sumptuous food and beverages are well-organized. The musical selections and the deejay makes you groove and stomp your feet. I met new folks and had a wonderful exchange with them. Cruising with Odyssey is cruising in excellence and it is reasonably priced.
Louise H
Solo
Verified booking
2 weeks ago
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.
Angel A
Family
Verified booking
3 weeks ago
Experience was adequate, most of the staff was friendly. The table servers had a lot of tables to cover, so they were in a rush to take your orders and serve you. We had a party of 7 and while we didn't go unattended frequent visit to see how we were doing were few and far between. They came by with a bread basket once! Food portions were small reminded me of a "Factor Meal" All in all for the price you pay to be on the ship I felt hustled.
Beth J
Couple
Verified booking
2 weeks ago
Our server Noa was with wonderful. And his helper Persia was a gem. We love the food, dessert, and DJ. The DJ got everyone on the dance floor and it was an exciting and exceptional that we want to do again already. We highly highly recommend booking a cruise. So worth it! The views and crew were amazing!
Karla J
Group
Verified booking
3 weeks ago
This is my first time to Chicago, and I had the best time. The staff on the cruise was so nice, Deena, Bri, and Peter really made us feel so welcomed. The music, food and the view was great! We plan to do this again the next time we visit Chicago. Thanks so much for a wonderful experience.

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.