Sightseeing Cruises

Odyssey Chicago River Architecture Dinner Cruise

Guests dining on Chicago Premier Plus Dinner Cruise with city skyline views.

Boat "Odyssey Chicago River" cruising on Chicago River with skyscrapers and bridge.

Couple dining by a window with city and water view at night.

Chicago skyline with skyscrapers along the river, Illinois, USA.

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

4.6/5(47)

Hollie M

Couple

Verified booking

May 2026

Really enjoyable evening on the dinner cruiser, scenery and food was amazing! Our waiter Wesley was great too! The only thing is the aircon was on full and everyone was eating in their coats, I did ask if it could be turned down abit but it couldn't. It wasn't a particularly warm evening either...apart from that we really enjoyed it!

Nakisha A

Couple

Verified booking

2 weeks ago

I absolutely loved the view, the food, and the drinks...everyone was so friendly and welcoming...I've never had dinner on the water so that was definitely a great experience, I took my fiancé for his bday and he never been there so that was great seeing his face and how much he loved it 🥰

Tracy H

Couple

Verified booking

Last week

Our server was Edgar. He was attentive and professional in meeting our needs. David the DJ set the vibes with good music. Food, fun, and river views were wonderful. Highly recommended

Mustafa I

Group

Verified booking

3 weeks ago

Friendly staff, beautiful route, great seating. We had a minor issue with the order, but they got it all fixed. Generous portions and nice surrounding music.

Tanisha H

Couple

Verified booking

Apr 2026

Cruising down the river and looking up at spots like the Wrigley Building and Willis Tower just hit different from the water. You really see the details, the mix of old-school and modern, and how everything fits together. But the best part? The vibe. It’s calm, a little breezy, the city reflecting off the water… and you lowkey feel like you seeing Chicago from a whole new angle—even if you’ve lived here your whole life. If I had to sum it up real simple: It felt like a history lesson, a skyline view, and a peaceful reset all in one.

Dorian C

Couple

Verified booking

Apr 2026

That was the most amazing bus ride I ever had. Our tour guide was awesome. She knew all of her stuff about the city very fun loving outgoing made the trip. Very interesting. Fun to be around.. the bus driver did an awesome job of driving the bus kudos to her..

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.

47 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
Shunya B
Couple
Verified booking
Yesterday
We had a wonderful time!! Everything was great!
Hollie M
Couple
Verified booking
May 2026
Really enjoyable evening on the dinner cruiser, scenery and food was amazing! Our waiter Wesley was great too! The only thing is the aircon was on full and everyone was eating in their coats, I did ask if it could be turned down abit but it couldn't. It wasn't a particularly warm evening either...apart from that we really enjoyed it!
Nakisha A
Couple
Verified booking
2 weeks ago
I absolutely loved the view, the food, and the drinks...everyone was so friendly and welcoming...I've never had dinner on the water so that was definitely a great experience, I took my fiancé for his bday and he never been there so that was great seeing his face and how much he loved it 🥰
Tracy H
Couple
Verified booking
Last week
Our server was Edgar. He was attentive and professional in meeting our needs. David the DJ set the vibes with good music. Food, fun, and river views were wonderful. Highly recommended
Mustafa I
Group
Verified booking
3 weeks ago
Friendly staff, beautiful route, great seating. We had a minor issue with the order, but they got it all fixed. Generous portions and nice surrounding music.

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