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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(248)

Beth J

Couple
Verified booking
Yesterday
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
4 days 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.

Localzo J

Couple
Verified booking
Jun 2026
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.

Michael S

Group
Verified booking
2 weeks ago
The crew and servers very friendly. Our host could have checked on us. The second half only saw him once. He still did a great job and I gave a 20 tip to him. The food was delicious, everything was clean and tiddy. One thing caught my eye though. I had called about dress code. My wife dress, me suit and tie. Our daughter jeans and a blouse at least. I was told on the phone dress smart casual. One male guest had a sleeveless tank undershirt. So aside from seeing his arm pits it truly was an amazing experience. I didn't mention to the crew. It wasn't the end of the world. I'm sure we will return for another dinner cruise. Over all great value for a wonderful evening. The fuzeball table was a great surprise. The DJ was very friendly and engaging. The crowd like myself a bunch of sitters not dancing. We danced one slow song though. My wife had a tough time dancing with the boat motion. She lovesto dance normally. Thank you very much. I will highly recommend to all my friends to try.

Andres M

Couple
Verified booking
2 weeks ago
The Chicago Dinner Cruise was an absolutely magical experience! The views of the skyline from the water were breathtaking, especially as the sun set and the city lights began to sparkle. The dining experience exceeded my expectations with delicious food and great service throughout the evening. It was the perfect atmosphere for a special night out. I highly recommend this to anyone looking to enjoy the beauty of Chicago from a unique perspective!

Brianna J

Solo
Verified booking
3 weeks ago
The staff was very welcoming and accomodating. My server, Sarah was very attentitve. I didn't expect there to be a DJ or a dance floor so that was a nice surprise! The viewing decks offered great views from every floor. The food was actually quite delicious and so were the drinks. I celebrated my birthday on the cruise and they surprised me with a Happy Birthday message on my dessert. I was cruising alone so it felt very special.
    • 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.

  • 248 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.

    197
    22
    18
    5
    6
    Mexico
    United Kingdom
    Canada
    Egypt
    Ecuador
    France
    Ukraine
    Philippines
    Mexico
    United Kingdom
    Canada
    Egypt
    Ecuador
    France
    Ukraine
    Philippines
    Guests from Mexico, United Kingdom, Canada and over 9 countries have loved this experience

    What our guests say

    Thomas L

    Couple
    Verified booking
    Last week
    The 4 rating I gave you is actually misleading. The experience was a 4, but you started out at 3 due to the backdrop and boat being perfect... which was little to no-doing on your service end. The wait staff was ok, not good, not great. Ok. The food was below average, felt like we were being fed wedding buffet food that was cooked half-assed and barely seasoned. Cheesecake was great, but I'm guessing that they were purchased, not baked by your company. Regarding the sound/entertainment, this was embarrassing. First, you implied an architectural tour of the river... not one thing was mentioned, this was actually a bit of fraud in my opinion, you literally had 0 entertainment. It was us just floating down the river and coming back. Cool, but not what you marketed... almost asked for my money back on that. Then there was the sound, Jesus Christ... what a horrible, distorted, muffled, ridiculous experience you offer. I am an audio engineer and multimedia professional, and it was laughable how bad this was. Without the amazing backdrop and boat, you'd get a 1 star. The ambiance and vibe is obviously what's carrying your business, but charging essentially 200+ a person, to me, deserves a better experience on your end.

    Michael S

    Group
    Verified booking
    2 weeks ago
    The crew and servers very friendly. Our host could have checked on us. The second half only saw him once. He still did a great job and I gave a 20 tip to him. The food was delicious, everything was clean and tiddy. One thing caught my eye though. I had called about dress code. My wife dress, me suit and tie. Our daughter jeans and a blouse at least. I was told on the phone dress smart casual. One male guest had a sleeveless tank undershirt. So aside from seeing his arm pits it truly was an amazing experience. I didn't mention to the crew. It wasn't the end of the world. I'm sure we will return for another dinner cruise. Over all great value for a wonderful evening. The fuzeball table was a great surprise. The DJ was very friendly and engaging. The crowd like myself a bunch of sitters not dancing. We danced one slow song though. My wife had a tough time dancing with the boat motion. She lovesto dance normally. Thank you very much. I will highly recommend to all my friends to try.

    James F

    Couple
    Verified booking
    Last week
    The food, views, drinks and music. I have to say that almost all servers didn't appear to be enjoying their job. Very few smiles, not much conversation. Our server came right away to take our order when we wanted to start with a cocktail first. He then proceeded to go to two other tables before taking our drink order. I understand they have a schedule to stay on, but it took forever to get a drink after we told him we didn't want our food right then. It's still a wonderful cruise to take while visiting Chicago. This was our 3rd or 4th time to go. The views are amazing. Highly recommend! Because we have been and have taken pictures in the past, I did not take pictures this time.

    Angel A

    Family
    Verified booking
    6 days 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.

    Andres M

    Couple
    Verified booking
    2 weeks ago
    The Chicago Dinner Cruise was an absolutely magical experience! The views of the skyline from the water were breathtaking, especially as the sun set and the city lights began to sparkle. The dining experience exceeded my expectations with delicious food and great service throughout the evening. It was the perfect atmosphere for a special night out. I highly recommend this to anyone looking to enjoy the beauty of Chicago from a unique perspective!
  • 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.

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