Chicago Cruise Departures

Cruises that depart from North America: United States: Illinois: Chicago

Cruises that visit Chicago

Click on a cruise ship itinerary sailing from Chicago (below) and select a sail date to receive competing cruise quotes. To search all cruise itineraries (not just Chicago), please visit: Cruise Search or try our Virtual Cruise Advisor™.

Blount Small Ship Adventures, Grande Mariner

7 Night Magical Lake Michigan roundtrip from Chicago, IL
Starting in Chicago, IL; with stops in Holland, MI; Beaver Island, MI; Mackinac Island, MI; Sturgeon Bay, WI; Milwaukee, WI
2019 Sails: Aug 15, Aug 24, More...

Blount Small Ship Adventures, Grande Caribe

13 Night Chicago to Montreal
Starting in Chicago, IL; with stops in Sturgeon Bay, WI; Mackinac IS, MI; Wyandotte, MI; Cleveland, OH; Buffalo, NY; Toronto, ON; Kingston, ON; Upper Canada Village Montreal, QC
2019 Sails: Aug 28, More...

Blount Small Ship Adventures, Grande Mariner

15 Night Great American Waterways from Chicago to New York
Starting in Chicago, IL; with stops in Manitowoc, WI; Mackinac Island, MI; Wyandotte, MI; Cleveland, OH; Buffalo, NY; Rochester, NY; Oswego, NY; Sylvan Beach, NY; Amsterdam, NY; Troy, NY; Kingston, NY; West Point, NY; New York, NY
2019 Sails: Sep 3, More...