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(515)

Mychal A

Couple
Verified booking
3 days ago
The hospitality was beyond amazing!!! It was my girlfriends birthday and the manager comped some birthday items and it was amazing and extremely fun and made her smile so much!!! We loved the food and just the. One of the entire night all together!!!! Will for sure be doing this again!!!

Jay E

Couple
Verified booking
2 weeks ago
The dinner cruise aboard the Odessy was a good time and such a vibe. If you are looking for something out of the ordinary to do in Chicago, whether you are celebrating something special or looking for a nice date night option, this is definitely worth it. The staff was very attentive and polite. The food was actually pretty good and the variety of drinks were well balanced, offering something for everyone. Despite the rainy weather that hindered the enjoyment of the outer decks, the total experience was great enough that we'll definitely look to try this again.

Olivia C

Couple
Verified booking
3 weeks 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.

Emmanuel H

Couple
Verified booking
5 days ago
We had an amazing experience on the Odyssey Lake Michigan Dinner Cruise! Everything was wonderful, from the delicious food to the beautiful views of Chicago from the water. The atmosphere was romantic and relaxing, and our server, Joaquin, was fantastic—friendly, attentive, and made sure we had everything we needed throughout the evening. He really helped make our experience special. We would definitely recommend this cruise and would love to come back again!

Melvin D

Couple
Verified booking
3 weeks ago
We celebrated our anniversary aboard the Odyssey Chicago River dinner cruise, and it was truly a memorable experience. The food was delicious, the service was attentive, and the beautiful nighttime views of the Chicago skyline made the evening feel especially romantic. The atmosphere, music, and time together on the water created the perfect anniversary celebration. We would definitely recommend this cruise to other couples looking for a special night out.

Sandra F

Group
Verified booking
Sep 2026
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.
    • 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.

  • 515 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.

    395
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    Mexico
    Canada
    United Kingdom
    Egypt
    Iceland
    Serbia
    Argentina
    Ecuador
    France
    Philippines
    Mexico
    Canada
    United Kingdom
    Egypt
    Iceland
    Serbia
    Argentina
    Ecuador
    France
    Philippines
    Guests from Mexico, Canada, United Kingdom and over 13 countries have loved this experience

    What our guests say

    Brenda S

    Couple
    Verified booking
    3 weeks ago
    The food was ok. Our starters were cold. The menu was very limited. I ended up ordering a steak, which was not cooked as requested (well done). The servers were very attentive though. The music was nice and the views at night was spectacular.

    Paul M

    Couple
    Verified booking
    2 weeks ago
    Food was great...atmosphere was great, music was great....and the staff was very welcoming...i will do this again!!! Cannot beat the views of they city!!

    Aissa B

    Solo
    Verified booking
    3 weeks 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!

    Jay E

    Couple
    Verified booking
    2 weeks ago
    The dinner cruise aboard the Odessy was a good time and such a vibe. If you are looking for something out of the ordinary to do in Chicago, whether you are celebrating something special or looking for a nice date night option, this is definitely worth it. The staff was very attentive and polite. The food was actually pretty good and the variety of drinks were well balanced, offering something for everyone. Despite the rainy weather that hindered the enjoyment of the outer decks, the total experience was great enough that we'll definitely look to try this again.

    Olivia C

    Couple
    Verified booking
    3 weeks 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.

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