Chicago Cruises
Cruises that visit North America: United States: Illinois: Chicago
16 Night - Niagara & Great Lakes Treasures
Starting in Toronto, Ontario, Welland Canal, Niagara Falls (Port Colborne), Ontario, Point Pelee, Ontario, Detroit, Michigan, Alpena, Michigan, Mackinac Island, Michigan, Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin
2026 Sails: May 1, More...16 Night - Niagara & Great Lakes Treasures
Starting in Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin, Mackinac Island, Michigan, Alpena, Michigan, Detroit, Michigan, Point Pelee, Ontario, Niagara Falls (Port Colborne), Ontario, Welland Canal, Toronto, Ontario
2026 Sails: May 8, More...9 Night - Great Lakes Treasures
Starting in Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin
2026 Sails: May 8, More...
9 Night - Great Lakes Treasures
Starting in Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin
2026 Sails: May 17, May 26, Jun 18, Jun 27, Sep 14, Sep 23, 2028: May 16, May 25, Jul 24, More...16 Night - Niagara & Great Lakes Treasures
Starting in Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin, Mackinac Island, Michigan, Alpena, Michigan, Detroit, Michigan, Point Pelee, Ontario, Niagara Falls (Port Colborne), Ontario, Welland Canal, Toronto, Ontario
2026 Sails: May 26, Jun 27, Sep 23, 2028: May 25, More...16 Night - Niagara & Great Lakes Treasures
Starting in Toronto, Ontario, Welland Canal, Niagara Falls (Port Colborne), Ontario, Point Pelee, Ontario, Detroit, Michigan, Alpena, Michigan, Mackinac Island, Michigan, Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin
2027 Sails: May 6, More...9 Night - Great Lakes Treasures
Starting in Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin
2027 Sails: May 13, May 22, Aug 23, Sep 1, More...16 Night - Niagara & Great Lakes Treasures
Starting in Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin, Mackinac Island, Michigan, Alpena, Michigan, Detroit, Michigan, Point Pelee, Ontario, Niagara Falls (Port Colborne), Ontario, Welland Canal, Toronto, Ontario
2027 Sails: May 22, Sep 1, More...16 Night - Niagara & Great Lakes Treasures
Starting in Toronto, Ontario, Welland Canal, Niagara Falls (Port Colborne), Ontario, Point Pelee, Ontario, Detroit, Michigan, Alpena, Michigan, Mackinac Island, Michigan, Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin
2027 Sails: Aug 16, More...16 Night - Niagara & Great Lakes Treasures
Starting in Toronto, Ontario, Welland Canal, Niagara Falls (Port Colborne), Ontario, Point Pelee, Ontario, Detroit, Michigan, Alpena, Michigan, Mackinac Island, Michigan, Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin
2028 Sails: May 9, More...
Cruises that visit North America: United States: Illinois: Chicago
Click on a cruise ship itinerary that visits 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™.
16 Night - Niagara & Great Lakes TreasuresStarting in Toronto, Ontario, Welland Canal, Niagara Falls (Port Colborne), Ontario, Point Pelee, Ontario, Detroit, Michigan, Alpena, Michigan, Mackinac Island, Michigan, Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin
2026 Sails: May 1, More...
16 Night - Niagara & Great Lakes TreasuresStarting in Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin, Mackinac Island, Michigan, Alpena, Michigan, Detroit, Michigan, Point Pelee, Ontario, Niagara Falls (Port Colborne), Ontario, Welland Canal, Toronto, Ontario
2026 Sails: May 8, More...
9 Night - Great Lakes TreasuresStarting in Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin
2026 Sails: May 8, More...
9 Night - Great Lakes TreasuresStarting in Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin
2026 Sails: May 17, May 26, Jun 18, Jun 27, Sep 14, Sep 23, 2028: May 16, May 25, Jul 24, More...
16 Night - Niagara & Great Lakes TreasuresStarting in Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin, Mackinac Island, Michigan, Alpena, Michigan, Detroit, Michigan, Point Pelee, Ontario, Niagara Falls (Port Colborne), Ontario, Welland Canal, Toronto, Ontario
2026 Sails: May 26, Jun 27, Sep 23, 2028: May 25, More...
16 Night - Niagara & Great Lakes TreasuresStarting in Toronto, Ontario, Welland Canal, Niagara Falls (Port Colborne), Ontario, Point Pelee, Ontario, Detroit, Michigan, Alpena, Michigan, Mackinac Island, Michigan, Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin
2027 Sails: May 6, More...
9 Night - Great Lakes TreasuresStarting in Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin
2027 Sails: May 13, May 22, Aug 23, Sep 1, More...
16 Night - Niagara & Great Lakes TreasuresStarting in Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin, Mackinac Island, Michigan, Alpena, Michigan, Detroit, Michigan, Point Pelee, Ontario, Niagara Falls (Port Colborne), Ontario, Welland Canal, Toronto, Ontario
2027 Sails: May 22, Sep 1, More...
16 Night - Niagara & Great Lakes TreasuresStarting in Toronto, Ontario, Welland Canal, Niagara Falls (Port Colborne), Ontario, Point Pelee, Ontario, Detroit, Michigan, Alpena, Michigan, Mackinac Island, Michigan, Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin
2027 Sails: Aug 16, More...
16 Night - Niagara & Great Lakes TreasuresStarting in Toronto, Ontario, Welland Canal, Niagara Falls (Port Colborne), Ontario, Point Pelee, Ontario, Detroit, Michigan, Alpena, Michigan, Mackinac Island, Michigan, Milwaukee, Wisconsin, Mackinac Island, Michigan, Georgian Bay (Killarney), Ontario, Georgian Bay (Frazer Bay), Ontario, Fathom Five National Marine Park, Ontario, The Benjamin Islands North Channel, Sault Sainte Marie, Michigan, Door Peninsula (Algoma), Wisconsin, Chicago, Illinois, Milwaukee, Wisconsin
2028 Sails: May 9, More...
