Sightseeing Cruises

Odyssey Chicago River Architecture Dinner Cruise

4.5/5(84)

Tom S

Group

Verified booking

2 weeks ago

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.

Louise H

Solo

Verified booking

Jul 2026

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.

Julian S

Couple

Verified booking

Jul 2026

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.

Darlene A

Solo

Verified booking

Jul 2026

The food was excellent, good vibes, excellent service, and the view was beautiful. My group didn't like the drinks we order, they could do better in that area. Overall I still will give it a five star, loved the experience. Will do it again

Adrianne C

Couple

Verified booking

Jul 2026

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!!

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.

84 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
Tom S
Group
Verified booking
2 weeks ago
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
Rickie C
Couple
Verified booking
Last week
We had a fabulous time. It was worth every penny. The food was delicious the service was 5 stars the vibe was beautiful!
Winthrop W
Couple
Verified booking
Last week
The crew was phenomenal, food was good...only issue was instructions how to actually get the the dock
Tiffany D
Couple
Verified booking
Aug 2026
Immaculate !!!! Top tier 👌. Food was amazing.
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.

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