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(449)

Olivia C

Couple
Verified booking
3 days ago
The cruise itself was so much fun! We loved it. I would say that our server was not the best, but he was still very nice and professional. Our food was fine, nothing crazy, but we did feel that it was unfortunate that should we want better food, we'd have to pay a significant amount. We already paid a significant amount for the base experience. I enjoyed that our food was made early, which meant that we spent most of the cruise on the observation deck. The crew of the boat were so nice and took many photos for us and for other guests.

Sandra F

Group
Verified booking
Last week
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.

Angela S

Couple
Verified booking
4 days ago
The food was good, the staff was very friendly and professional. The Dj was very good and got the crowd out dancing. It was a good time and weather was perfect.

Ashley T

Couple
Verified booking
Last week
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.

Courtney G

Couple
Verified booking
3 days ago
The dinner cruise was excellent! The views were beautiful and perfect. The food and beverage choices were on point. All of the staff were super helpful!

Aissa B

Solo
Verified booking
2 days ago
I had an amazing overall experience! The views, the cruise itself, and the atmosphere were all wonderful. The upper deck was especially beautiful and really added to the experience. It’s definitely something I would do again. I do, however, have a few concerns regarding the food and our server. I upgraded to the filet and requested it medium, but unfortunately, it came out well done and had very little seasoning. It was served with a horseradish sauce, which I personally didn’t care for, although I understand that is simply a matter of preference. Our server was also somewhat lackadaisical and not as attentive as I would have liked. We had to ask several times for our drinks before receiving them because of the delay. At one point, we went to the bar ourselves to get our drinks. When our server saw us, she said, “I told you that I do all the drinks for you.” While I understand what she meant, I didn’t feel that was the best response to give patrons, especially considering we had already been waiting. Despite these issues, the cruise was a fantastic experience overall. The atmosphere, views, and upper deck were amazing, and I would absolutely do it again!
    • 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

    Tribune Tower

    Wrigley Building

    Wrigley Building

    Merchandise Mart

    Merchandise Mart

    Civic Opera House

    Civic Opera House

    Willis Tower

    Willis Tower

    Wolf Point

    Wolf Point

    Marina City

    Marina City

    DuSable Bridge

    DuSable Bridge

    Aon Center

    Aon Center

    Trump International Tower

    Trump International Tower

    Navy Pier

    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

    Chicago Harbor Lighthouse

    Willis Tower

    Willis Tower

    John Hancock Center

    John Hancock Center

    Aqua Tower

    Aqua Tower

    The St. Regis Chicago

    The St. Regis Chicago

    Marina City

    Marina City

    Lake Point Tower

    Lake Point Tower

    Harbor Point

    Harbor Point

    340 on the Park

    340 on the Park

    Adler Planetarium

    Adler Planetarium

    Soldier Field

    Soldier Field

    Shedd Aquarium

    Shedd Aquarium

    Fireworks display

    Fireworks display

    TOTAL DURATION2 hours - 3 hours
    MODE OF TRANSFERCruise Ship

    1 Boarding point

    Navy Pier

    Get direction

    Sights covered

    Willis Tower

    Willis Tower

    John Hancock Center

    John Hancock Center

    Aon Center

    Aon Center

    Shedd Aquarium

    Shedd Aquarium

    Field Museum

    Field Museum

    Adler Planetarium

    Adler Planetarium

    Soldier Field

    Soldier Field

    Buckingham Fountain

    Buckingham Fountain

    Grant Park

    Grant Park

    Marina City

    Marina City

    Wrigley Building

    Wrigley Building

    Tribune Tower

    Tribune Tower

    Chicago Harbor

    Chicago Harbor

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

  • 449 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.

    342
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    Mexico
    United Kingdom
    Canada
    Egypt
    Serbia
    Argentina
    Ecuador
    France
    Philippines
    Italy
    Mexico
    United Kingdom
    Canada
    Egypt
    Serbia
    Argentina
    Ecuador
    France
    Philippines
    Italy
    Guests from Mexico, United Kingdom, Canada 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
    Aug 2026
    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.

    Aissa B

    Solo
    Verified booking
    2 days ago
    I had an amazing overall experience! The views, the cruise itself, and the atmosphere were all wonderful. The upper deck was especially beautiful and really added to the experience. It’s definitely something I would do again. I do, however, have a few concerns regarding the food and our server. I upgraded to the filet and requested it medium, but unfortunately, it came out well done and had very little seasoning. It was served with a horseradish sauce, which I personally didn’t care for, although I understand that is simply a matter of preference. Our server was also somewhat lackadaisical and not as attentive as I would have liked. We had to ask several times for our drinks before receiving them because of the delay. At one point, we went to the bar ourselves to get our drinks. When our server saw us, she said, “I told you that I do all the drinks for you.” While I understand what she meant, I didn’t feel that was the best response to give patrons, especially considering we had already been waiting. Despite these issues, the cruise was a fantastic experience overall. The atmosphere, views, and upper deck were amazing, and I would absolutely do it again!

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