Sightseeing Cruises

Odyssey Chicago River Architecture Dinner Cruise

Duration

2 hrs 30 mins

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

4.7/5(64)

Debonne W

Solo

Verified booking

Last week

I have wanted to do this cruise since December 2022. Odyssey Dinner Cruise offers a combination of amazing experiences for the solo, paired, or group travelers. From start to finish, the respect and courtesy are refreshingly exceptional. Thank you! Cruising along stretches of the Chicago River while viewing the city's impeccable architecture and ongoing construction projects makes it a high spirited trip. The cuisine and the time of serving the sumptuous food and beverages are well-organized. The musical selections and the deejay makes you groove and stomp your feet. I met new folks and had a wonderful exchange with them. Cruising with Odyssey is cruising in excellence and it is reasonably priced.

Louise H

Solo

Verified booking

Last week

Our evening on the Odyssey Chicago River Architecture Dinner Cruise was unforgettable. The views of Chicago’s iconic skyline and historic buildings were breathtaking, and the narration made the city’s architecture come alive. The staff was genuinely warm and attentive, the meal was delicious, and the atmosphere on board felt both elegant and relaxed. Watching the city lights reflect on the river while enjoying dinner with friends was a perfect experience. I would gladly recommend this cruise to anyone looking for a memorable way to experience Chicago.

Enjoy a 2.5–hour Chicago River cruise aboard the Odyssey, complete with a gourmet plated dinner and live, curated entertainment for an unforgettable evening on the water.

Marvel at Chicago’s iconic skyline and architectural masterpieces from a climate-controlled interior deck, with guaranteed seating and unlimited coffee, hot tea, iced tea, and water.

Elevate the evening with a window-table upgrade and take in the Lake Michigan views by the river’s glow.

Bring the whole family and enjoy free admission for infants under two.

Creative cocktails, wine, and beer are available on your cruise for purchase to add to your cruise, ideal for celebrations or a special night out.

2.5-hour Chicago River dinner cruise

Plated gourmet dinner

Live curated entertainment

Dinner cruise with fireworks (available on select dates from May to October) (as per option selected)

Additional beverages (available for purchase onboard)

TOTAL DURATION3 hours - 3 hours
MODE OF TRANSFERCruise Ship
1 Boarding point
Chicago River Esplanade
Sights covered
Tribune Tower

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

64 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.
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What our guests say
Debonne W
Solo
Verified booking
Last week
I have wanted to do this cruise since December 2022. Odyssey Dinner Cruise offers a combination of amazing experiences for the solo, paired, or group travelers. From start to finish, the respect and courtesy are refreshingly exceptional. Thank you! Cruising along stretches of the Chicago River while viewing the city's impeccable architecture and ongoing construction projects makes it a high spirited trip. The cuisine and the time of serving the sumptuous food and beverages are well-organized. The musical selections and the deejay makes you groove and stomp your feet. I met new folks and had a wonderful exchange with them. Cruising with Odyssey is cruising in excellence and it is reasonably priced.
Louise H
Solo
Verified booking
Last week
Our evening on the Odyssey Chicago River Architecture Dinner Cruise was unforgettable. The views of Chicago’s iconic skyline and historic buildings were breathtaking, and the narration made the city’s architecture come alive. The staff was genuinely warm and attentive, the meal was delicious, and the atmosphere on board felt both elegant and relaxed. Watching the city lights reflect on the river while enjoying dinner with friends was a perfect experience. I would gladly recommend this cruise to anyone looking for a memorable way to experience Chicago.
Adrianne C
Couple
Verified booking
2 weeks ago
This cruise was absolutely amazing! The views of my city on the river was so beautiful especially during the sunset. The food was just ok and could've been portioned better but the overall experience was EPIC!!
Thomas L
Couple
Verified booking
3 weeks ago
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.
Julian S
Couple
Verified booking
Last week
Great Experience, Good Food, Waiters/Waitresses did a great job at providing good service, AC was quite cold at the beginning but eventually got moderate. A bit loud with all the people but still a lot of room for quite intimate conversations. Would recommend to experience atleast once.

What to bring

A valid photo ID matching your reservation name for boarding verification.

Cocktail attire: collared shirts, sports coats, slacks, dresses, or blouses.

A light jacket or wrap for breezy open-air deck moments.

Any items needed for dietary accommodations (advance notice recommended).

What’s not allowed

Outside food or beverages.

Large bags, suitcases, or oversized luggage.

Pets, except for documented service animals.

Smoking or vaping anywhere on board.

Accessibility

Wheelchair-accessible ramps and ADA-compliant restrooms on board.

Crew assistance is available for guests with mobility needs.

Additional information

Boarding opens 30 minutes before departure (45 minutes on Sundays); check your confirmation for exact timing.

Departure point: Chicago River Esplanade, 455 N Cityfront Plaza Drive, Chicago, IL.

Infants under two cruise free when included in your booking.

Cruise lasts approximately 2.5–3 hours; times may vary slightly.

Your voucher will be emailed to you instantly.

Please arrive at the boarding point 15 mins before the scheduled time of your visit to avoid any delays.

Display the voucher on your mobile phone with a valid photo ID at the boarding point.

Boarding point

Board your cruise at City Cruises.

Address: 455 N Cityfront Plaza Dr, Chicago, IL 60611 .

Get directions to the boarding point