City Cruises, operator of Chicago's premier year-round water experiences, is excited to announce its Fall 2026 lineup, featuring festive seasonal cruises, holiday celebrations, thrilling 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 unforgettable ways to experience Chicago no matter the weather.
"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 hauntingly fun journey through the city's storied past. As the vessel cruises past Chicago's iconic architecture, expert 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. Blending fascinating local history with seasonal storytelling and spectacular city views, the limited-time experience provides a one-of-a-kind way to celebrate Halloween in Chicago.
Celebrate Marathon Weekend with Medal Monday Aboard Seadog
Following one of Chicago's most iconic athletic events, 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, making it the perfect way to celebrate an incredible accomplishment. Runners can take in stunning skyline views, enjoy a well-earned post-race experience, and commemorate their achievement with a high-energy ride aboard Chicago's favorite speedboat attraction.
Stars, Stories & Live Entertainment Take Center Stage with City Cruises Live This Fall
City Cruises Live returns for Fall 2026 with an exciting lineup of immersive experiences that bring country music and unforgettable entertainment to the water. Country music fans can set sail with Country Cruisin' with Chris Lane and Go Country Cruisin' with Joe Nichols, enjoying intimate live performances and stunning skyline views from the water. Together, these unique events transform Chicago's waterfront into one of the city's most exciting live entertainment destinations.
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 unforgettable skyline views in a unique 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. Guests can learn more about Thanksgiving, holiday, and seasonal cruises here.
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.
ABOUT CITY CRUISES
City Cruises creates amazing experiences for guests with unforgettable dining, events, sightseeing, and live entertainment cruises across 20 iconic destinations in the United States, Canada, and the United Kingdom. City Cruises’ diverse offerings also include private charters, corporate events, weddings, whale watching, water taxis, speedboat rides, and destination ferries. In partnership with the National Park Service and Niagara Parks, Statue City Cruises, Alcatraz City Cruises, and Niagara City Cruises serve as the official and exclusive ferry service operators to three of North America's most iconic destinations: the Statue of Liberty and Ellis Island, Alcatraz Island, and Niagara Falls, Canada. As part of Hornblower Group’s extensive portfolio, City Cruises has a rich heritage dating back to 1926 with the founding of Boston Harbor Cruises. With a legacy of innovation and expertise, City Cruises sets the standard for excellence in maritime hospitality. For more information, visit citycruises.com.