Love the idea of river cruising with the kids but don’t want to spend the time or money to fly everyone to Europe or take a week off from work? Or maybe you’ve never taken a cruise before and just want to dip your toe into the experience before signing up for something longer and more expensive. One solution might be the brand new Odyssey Chicago River cruise, which began cruising Sept. 28, and which offers a new way to enjoy the Windy City — but without the commitment.

Odyssey Chicago River cruise © Entertainment Cruises
The new, 140-foot vessel, custom designed for the Chicago River, is glass-enclosed so passengers can take in 360-degree panoramic views of the city’s best-known architecture. It holds up to 200 passengers, and offers lunch, brunch, cocktail parties, dinner cruises and special group events — have a birthday party or reunion coming up? — for you and your family.
The Odyssey Chicago River is also easy to get to, thanks to its dock along the River Esplanade in front of NBC Tower and just a few steps from the Magnificent Mile.
Once onboard, the itinerary wends westward along the river at a leisurely pace, exploring both its north and south branches. The route allows passengers to see the city’s skyline and riverbank from exterior observation spaces at the bow and stern or from the temperature-controlled dining room.

Arrival © Entertainment Cruises
Kids old enough to appreciate gourmet dining will probably enjoy the multicourse menu options created by executive chef Francesco Simone, who whips up specialties such as forest mushroom ravioli served with Spanish red lentils, while parents and young adults can choose from a curated selection of cocktails, spirits and wines.
If the cruise leaves you wanting more, Odyssey’s parent company, Entertainment Cruises, which operates the year-round cruise, is gearing up to partner with local businesses to host a program of unique experiences inspired by city events and culinary trends. The programs are being designed to appeal to a wide range of interests and to local Chicagoans as well as visitors.

Odyssey Chicago River cruise © Entertainment Cruises
For example, timed to coincide with the inaugural sailings, Odyssey Chicago River teamed up with City Winery to offer special wine selections for enthusiasts of all levels.
Odyssey Chicago River is the second vessel under the Odyssey brand in Chicago, joining sister ship, Odyssey Lake Michigan, which already offers upscale dining cruises on Lake Michigan from Navy Pier. With this newest vessel, Entertainment Cruises will now operate a choice of 10 ships across five different brands in the city.
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