Dinner Cruises

Chicago Dinner Cruise

4.6/5(397)

Banquetta F

Solo

Verified booking

5 days 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

5 days 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.

Eleonora L

Couple

Verified booking

2 weeks ago

Everything was absolutely perfect! The onboard staff were incredibly kind and welcoming, and our waiter, Adam, was attentive, friendly, and always happy to help. The food, the organization, and the table they gave us right by the window were all wonderful. The view was amazing, and we were also lucky enough to have perfect weather. Everything was simply perfect from start to finish. Highly recommended!

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.

397 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.
304
47
26
7
13
Guests from Mexico, Canada, United Kingdom and over 12 countries have loved this experience
What our guests say
Vanessa W
Couple
Verified booking
3 weeks ago
Overall, the boat cruise was a great experience\. The food was delicious, the staff was friendly and attentive, and the scenery and atmosphere were beautiful\. Everything was set up nicely and had the potential to be an amazing time\. Unfortunately, the DJ completely ruined the vibe\. The music selection was terrible, there was no energy, and it never got the crowd engaged\. On a cruise like this, the DJ really sets the tone for the entire experience, and this one missed the mark\. If the cruise gets a new DJ, I would definitely recommend it\. Everything else was great, but the entertainment needs a major upgrade\.
Gianna B
Couple
Verified booking
3 weeks ago
PHENOMENAL!! And legit! Such an amazing experience, amazing food, SO romantic, staff and DJ were very kind! It honestly felt too good to be true at some moments, but it was an amazing experience and I would definitely do it again!
Ashley B
Couple
Verified booking
Last week
i i enjoyed the atmosphere. it was calm and romantic, it was an amazing experience. it was the best date/half anniversary we could have. we are going to add this experience to once a year
Beatrice N
Group
Verified booking
3 weeks ago
My husband and I gifted 2 other couples to join us on the dinner cruise on Lake Michigan last week. We were all celebrating our wedding anniversary and my birthday. The service was impressive starting before we boarded. Next, was this watermelon spritzer drink. It was so delicious. The 3rd impressive experience was our meals which did not disappoint; between us we had the salmon, chicken, steak dinners. All plates were cleaned. To top off our meal we had the cheesecake. OMG! It was so rich with flavor and the texture was so smooth. The food was of good quality. The music was on point the entire time. The DJ had a great disposition. All of the staff was wonderful. We truly enjoyed the Odessey Lake Michigan Dinner Cruise experience. It allowed us to make wonderful memories as a part of celebrating our milestone anniversaries and my birthday. We will certainly be back for more and recommend to others. Thank you Odyssey.
Banquetta F
Solo
Verified booking
5 days 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

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.