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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.
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 15 Night Great American Waterways from Chicago to New York
15 Nights - 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: Jun 29, More... |
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13 Night Chicago to Montreal
13 Nights - 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... |
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 15 Night Great American Waterways from Chicago to New York
15 Nights - 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... |
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