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Chicago Cruise Departures

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

Cruises that visit Chicago

See all River Cruises that depart from 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™.


Ocean Navigator Cruises15 Night - Lakeside Treasures Cruise Roundtrip from Chicago
Starting in Chicago, IL (Embark); with stops in Mackinac Island, MI; Marquette, MI; Houghton, MI; Duluth, MN; Thunder Bay, ON; Sault Ste. Marie, MI; Green Bay, WI; Muskegon, MI; Chicago, IL
2022 Sails: Jun 4, Jun 18, 2023: Jun 2, Jun 16, More...
Ocean Voyager Cruises10 Night - Splendor of the Great Lakes Cruise from Chicago to Toronto
Starting in Chicago, IL (Embark); with stops in Chicago, IL; Scenic Sailing on Lake Michigan; Mackinac Island, MI; Sault Ste. Marie, MI; Little Current/Manitoulin Island, ON; Scenic Sailing on Lake Huron; Detroit, MI; Cleveland, OH; Niagara Falls (Port Colborne), ON; Toronto, ON
2022 Sails: Jun 7, Jun 25, Jul 13, Jul 31, Aug 18, Sep 5, 2023: Jun 13, Jul 1, Jul 19, Aug 6, Aug 24, More...
Ocean Navigator Cruises10 Night - Splendor of the Great Lakes Cruise from Chicago to Toronto
Starting in Chicago, IL (Embark); with stops in Chicago, IL; Scenic Sailing on Lake Michigan; Mackinac Island, MI; Sault Ste. Marie, MI; Little Current/Manitoulin Island, ON; Scenic Sailing on Lake Huron; Detroit, MI; Cleveland, OH; Niagara Falls (Port Colborne), ON; Toronto, ON
2022 Sails: Jul 2, Jul 20, Aug 7, 2023: May 15, Jun 30, Jul 18, Aug 5, 2024: Jun 20, Jul 8, Jul 26, Aug 13, More...
American Countess Cruises8 Night - Chicago (Ottawa) to St. Louis (Alton)
Starting in Chicago, IL; with stops in Ottawa, IL; Peoria, IL; Havana, IL; Hannibal, MO; Alton, IL; St. Louis (Alton)
2022 Sails: Aug 15, 2024: Jul 27, More...
Ocean Navigator Cruises12 Night - Great Lakes Grand Discovery Cruise from Chicago to Montreal
Starting in Chicago, IL (Embark); Scenic Sailing on Lake Michigan; with stops in Mackinac Island, MI; Sault Ste. Marie, MI; Little Current/Manitoulin Island, ON; Scenic Sailing on Lake Huron; Detroit, MI; Cleveland, OH; Niagara Falls (Port Colborne), ON; Toronto, ON; Scenic Sailing on Lake Ontario; Montreal, QC
2022 Sails: Aug 25, 2023: Aug 23, More...
Ocean Navigator Cruises14 Night - Great Lakes Grand Discovery Cruise from Chicago to Montreal
Starting in Chicago, IL (Embark); Scenic Sailing on Lake Michigan; with stops in Mackinac Island, MI; Sault Ste. Marie, MI; Little Current, ON; Scenic Sailing on Lake Huron; Detroit, MI; Cleveland, OH; Port Colborne (Niagara Falls), ON; Toronto, ON, Canada; Gananoque, ON; Montreal, QC (Disembark)
2022 Sails: Sep 18, More...
Ocean Voyager Cruises12 Night - Great Lakes Grand Discovery Cruise from Chicago to Montreal
Starting in Chicago, IL (Embark); Scenic Sailing on Lake Michigan; with stops in Mackinac Island, MI; Sault Ste. Marie, MI; Little Current/Manitoulin Island, ON; Scenic Sailing on Lake Huron; Detroit, MI; Cleveland, OH; Niagara Falls (Port Colborne), ON; Toronto, ON; Scenic Sailing on Lake Ontario; Montreal, QC
2022 Sails: Sep 23, 2023: Sep 29, 2024: Sep 6, Sep 28, More...

Chicago Cruise Departures

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