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.
Read This Next
#WhereverFamily
Insta FeedNorth America
Oct 16, 2026Subaru Finds Pets to Reshape 2026 Holiday Travels, Road Trip Plans
This week, Subaru released a report revealing just how central family pets are in holiday travel plans for Americans. The report found pet owners nationwide increasingly prioritize their animal companions when planning upcoming trips, so much so that 73 percent of U.S. drivers and pet owners surveyed said they’re more likely to bring their pet along.
Sponsored Content
Celebrating 25 Years of The Peninsula Chicago
June marked The Peninsula Chicago’s 25th anniversary, commemorating a quarter century for the hotel as a pillar of luxury on North Michigan Avenue.
Destinations / Europe
Oct 16, 2026Daytrip Ideas from Dublin, Ireland
A family vacation in Dublin, Ireland, doesn’t need to be limited to the sights and attractions in the city itself (although Dublin does have many amazing experiences). Visitors may be surprised by top Irish attractions within reach on a daytrip from the capital.
Destinations / North America
Oct 15, 2026Club Med Breaks Ground on Ultimate Mountain Vacation
Club Med officially announced the debut of its second mountain resort in Canada, set to open its doors in December 2028. Fully embracing the brand’s all-inclusive experience, Club Med Tremblant is designed to welcome both families and adults to its dynamic atmosphere.
Sponsored Content
GET TO KNOW TAP FORBIZ
Unlock flexible, refined business travel with TAP Air Portugal’s program, TAP FORBIZ. Developed for small, medium and large Companies, with options for corporate events, TAP FORBIZ offers exclusive advantages adapted to each type of business.
Destinations / North America
Oct 15, 2026Sharktober: What to Know Before Heading to Hawai’i This Month
Hawai’i’s beautiful weather makes it a great time to visit all year long, especially during shoulder season months when the weather is great, crowds are smaller and prices are lower. But if you’re heading there in October, there are a few things you’ll want to know before you go.
ShareThis