City Cruises, operator of Chicago’s year-round water experiences, announces its Fall 2026 lineup, featuring festive seasonal cruises, holiday celebrations, Seadog adventures, and exclusive City Cruises Live events across Lake Michigan and the Chicago River. While the seasons may change, City Cruises sails year-round, offering guests ways to experience Chicago no matter the weather.
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“Fall is one of the most exciting seasons on Chicago’s waterways,” said Grace Fuller, General Manager of City Cruises Chicago. “Whether guests are celebrating marathon weekend, embracing spooky season, or enjoying one of our unique City Cruises Live experiences, our fall lineup offers something for everyone. And with cruises operating year-round, there’s always a reason to get out on the water and experience Chicago from a new perspective.”
Haunted River Tours Bring Chicago’s Darkest Legends to Life
As Halloween season arrives, the Seadog Haunted River Tour returns to the Chicago River, offering guests a journey through the city’s storied past. As the vessel cruises past Chicago’s architecture, guides bring to life tales of infamous mobsters, unsolved mysteries, ghostly sightings, and historic tragedies that continue to captivate locals and visitors alike. Guests can fully embrace the spooky season with costumes encouraged, BYOB beverages welcome, and dogs invited aboard for the ride.
Celebrate Marathon Weekend with Medal Monday Aboard Seadog
Following the Chicago Marathon, Seadog’s Medal Monday sailings invite marathon participants to continue the celebration on the water. Guests who show their Chicago Marathon medal at the ticket booth can receive 50% off their cruise. Runners can take in skyline views, enjoy a post-race experience, and commemorate their achievement with a ride aboard Chicago’s speedboat attraction.
Stars, Stories & Live Entertainment Take Center Stage with City Cruises Live This Fall
City Cruises Live returns for Fall 2026 with a lineup of immersive experiences that bring country music and entertainment to the water. Country music fans can set sail with Country Cruisin’ with Chris Lane and Go Country Cruisin’ with Joe Nichols, enjoying live performances and skyline views from the water.
Plan Ahead for Holiday Celebrations and Seasonal Savings
Guests looking ahead to the holiday season can begin planning Thanksgiving gatherings, holiday celebrations, corporate events, and end-of-year outings aboard City Cruises Chicago’s signature dining vessels on Lake Michigan and the Chicago River. Whether celebrating with family, friends, clients, or colleagues, guests can enjoy chef-prepared dining, live entertainment, and skyline views in a waterfront setting.
To make planning even easier, City Cruises is offering a variety of seasonal promotions, including 30% Off Fall Dining Cruises available now through October 4 for sailings through December 13, as well as upcoming Black Friday and Cyber Week savings opportunities. For ticket information and details about all cruises departing from Chicago this fall season, visit www.citycruises.com/chicago and follow on Instagram and TikTok at @citycruises.