Headout logo. Link to home.

Help

Sell on Headout
Dinner Cruises

Chicago Dinner Cruise

Couple dining on a Chicago dinner cruise with city skyline views.
Chicago skyline with illuminated skyscrapers and river at dusk, Illinois, USA.
Dinner cruise guests enjoying Chicago skyline views through glass windows.
Chicago River at sunset with city skyline and illuminated buildings.

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(164)

Localzo J

Couple
Verified booking
4 days ago
As a first-time visitor to Chicago, the Odyssey Dinner Cruise on Lake Michigan was truly one of the highlights of my trip. From the moment I boarded, I was impressed by the professionalism and friendliness of the staff. Every crew member was welcoming, attentive, and committed to making sure guests had an enjoyable experience. The food was absolutely delicious. Each course was well-prepared, flavorful, and exceeded my expectations for dining on a cruise. The service throughout the evening was excellent, and the staff consistently went above and beyond to ensure everyone was comfortable and taken care of. The views were simply breathtaking. Watching the Chicago skyline light up at sunset while cruising on Lake Michigan created memories I will never forget. The combination of the city lights, the beautiful water, and the relaxing atmosphere made for an unforgettable evening. Overall, this was an outstanding experience from start to finish. As someone visiting Chicago for the first time, I couldn't have asked for a better way to see the city. I highly recommend the Odyssey Dinner Cruise to anyone looking for a memorable night out. I will definitely be returning on my next trip to Chicago and look forward to experiencing it again.

Josiah C

Couple
Verified booking
5 days ago
My wife and I first time we did something like this it was definitely fun food was good could be better but overall it was fun definitely a repeat experience

Kevin S

Couple
Verified booking
Last week
We celebrated our third wedding anniversary on the boat. This was the first- time experience for both of us. We were greeted warmly by all the employees as we boarded. The only issue I had was thinking that the electronic tickets were sufficient to board the boat. It would have been helpful to know that we still had to go to the ticket kiosk so we could get physical tickets to board. The website could have had a message (like a banner) to let you know to go to the kiosk to get physical tickets. Perhaps, some step-by-step instructions after you purchase your on-line tickets. Once we boarded the host seated us at our table. She was very friendly and asked if we had been on it before and whether we were celebrating any special occasion. It would've been nice if she asked if we wanted a window table. Later we saw other people relocate from an interior table to one next to the window. Later one of the DJs came to the table and asked us if we were celebrating and if we wanted a shoutout from the DJ. Overall, we had a wonderful first experience and would love to return.

Gabriela S

Group
Verified booking
May 2026
Without a doubt, one of my best experiences. I would take this cruise again and again. We were absolutely delighted—they even wished my sister a happy birthday over the PA system. They made us feel so special. The food was delicious, and we could eat as much as we wanted of everything included, right down to dessert. We don’t speak English, but the staff did their best to make sure we understood everything. They even took a souvenir photo of us—I loved it ❤️ If you visit the area, taking this cruise is the best thing you can do ❤️❤️

Iris W

Couple
Verified booking
6 days ago
The food was amazing , the staff was amazing and the dj kept a lot of different songs in rotation for all age groups. This was definitely a great way for me to spend my birthday. Big shout out to "lexi" I believe she was very helpful. My only complaint is the cruise was very cold , so bring a jacket. I know we were on the water but it was a lot my cold than I expected. Gret food and vibe for great price.

Miguel T

Couple
Verified booking
2 weeks ago
This was our first time going. We celebrated my Wife's birthday. Adam was our server this night and had provided the best service we have ever had. The music was excellent. Shout out the the DJ. The crew was very informative, helpful, and polite. The food went beyond my expectations. I cannot put into words how amazing the whole experience was. 100/10.
    • 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.

  • 164 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.

    132
    11
    11
    5
    5
    Egypt
    United Kingdom
    Canada
    France
    Mexico
    Philippines
    Egypt
    United Kingdom
    Canada
    France
    Mexico
    Philippines
    Guests from Egypt, United Kingdom, Canada and over 7 countries have loved this experience

    What our guests say

    Localzo J

    Couple
    Verified booking
    4 days ago
    As a first-time visitor to Chicago, the Odyssey Dinner Cruise on Lake Michigan was truly one of the highlights of my trip. From the moment I boarded, I was impressed by the professionalism and friendliness of the staff. Every crew member was welcoming, attentive, and committed to making sure guests had an enjoyable experience. The food was absolutely delicious. Each course was well-prepared, flavorful, and exceeded my expectations for dining on a cruise. The service throughout the evening was excellent, and the staff consistently went above and beyond to ensure everyone was comfortable and taken care of. The views were simply breathtaking. Watching the Chicago skyline light up at sunset while cruising on Lake Michigan created memories I will never forget. The combination of the city lights, the beautiful water, and the relaxing atmosphere made for an unforgettable evening. Overall, this was an outstanding experience from start to finish. As someone visiting Chicago for the first time, I couldn't have asked for a better way to see the city. I highly recommend the Odyssey Dinner Cruise to anyone looking for a memorable night out. I will definitely be returning on my next trip to Chicago and look forward to experiencing it again.

    Josiah C

    Couple
    Verified booking
    5 days ago
    My wife and I first time we did something like this it was definitely fun food was good could be better but overall it was fun definitely a repeat experience

    Karen W

    Couple
    Verified booking
    2 days ago
    I loved the view! The boat and the staff are all lovely. But my meal was terrible. The gnocchi dish was terrible! Bland

    Brian D

    Couple
    Verified booking
    3 days ago
    Great food, friendly staff and beautiful views of the Chicago skyline.

    Shunya B

    Couple
    Verified booking
    5 days ago
    We had a wonderful time!! Everything was great!
  • 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.
Download app section background

We've served 51 million+ guests and we are here for you

51 million+

Happy customers across 10,000+ experiences

In the media

Featured and recommended by the best brands

24 x 7 help center

Have a question? Live chat with local experts anywhere, anytime