Sightseeing Cruises

Odyssey Chicago River Architecture Dinner Cruise

4.5/5(103)

Veronica P

Group

Verified booking

Last week

When setting this experience, we honestly did not expect much. Boy, were we wrong! Edgar really made the experience a memorable one. We were there to celebrate our friends getting married, once Edgar found out he brought over champagne and took us to the front of the boat and took pictures of us. We had the short rib and upgraded to the ribeye and they were both cooked to perfection. They had a great selection of wines and the cocktails were just as great. The service from Edgar was above and beyond. We ran into one of the chefs outside and thanked her for her service. We do look forward to doing this again. Thank you for a memorable evening.

Valentina M

Couple

Verified booking

Last week

The restaurant is very pretty, the customer service is good, and the food was delicious. 2.5 hours is more than enough time to enjoy a great meal and beautiful views of the Chicago River.

David F

Solo

Verified booking

5 days ago

It was great to meet new people and enjoy great food. The views from the bow were amazing! I wish the lights would have been dimmed so I could enjoy the views from inside better (it was a little chilly!)

Brenda S

Couple

Verified booking

Sep 2026

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.

Tom S

Group

Verified booking

Aug 2026

The sites were great. The ship overall, was very nice However, out server was not very attentive, and the ramp boarding the ship was ridiculously steep and insafe

Debonne W

Solo

Verified booking

Jul 2026

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.

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
Wrigley Building
Merchandise Mart
Civic Opera House
Willis Tower
Wolf Point
Marina City
DuSable Bridge
Aon Center
Trump International Tower
Navy Pier

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

103 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
Veronica P
Group
Verified booking
Last week
When setting this experience, we honestly did not expect much. Boy, were we wrong! Edgar really made the experience a memorable one. We were there to celebrate our friends getting married, once Edgar found out he brought over champagne and took us to the front of the boat and took pictures of us. We had the short rib and upgraded to the ribeye and they were both cooked to perfection. They had a great selection of wines and the cocktails were just as great. The service from Edgar was above and beyond. We ran into one of the chefs outside and thanked her for her service. We do look forward to doing this again. Thank you for a memorable evening.
David F
Solo
Verified booking
5 days ago
It was great to meet new people and enjoy great food. The views from the bow were amazing! I wish the lights would have been dimmed so I could enjoy the views from inside better (it was a little chilly!)
Valentina M
Couple
Verified booking
Last week
The restaurant is very pretty, the customer service is good, and the food was delicious. 2.5 hours is more than enough time to enjoy a great meal and beautiful views of the Chicago River.
Tara A
Couple
Verified booking
Last week
Beautiful night! Staff was amazing, did was playing all the right music, food and drinks were fire! We had the best time! 10/10 recommend!
Sherman R
Solo
Verified booking
Last week
Honestly, it was an incredible experience, I would definitely do it again.

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