Chicago cruises

Cruise offers on sale now, with ships, departure dates and prices. Choose a line or region to narrow the list.

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4 on sale

Alaska Cruise & Rockies Sleeper Train from Seattle to Chicago- 12 Nights

Ketchikan · MSC Cruises · MSC Poesia

25 Apr 2027 – 8 May 2027

£2,239

Chicago Sleeper Train to Seattle and Alaskan Quantum Cruise- 12 Nights

Chicago · Royal Caribbean · Quantum of the Seas

28 Apr 2027 – 11 May 2027

£2,419

Alaska & Rockies Express to Chicago All-Inclusive Cruise

Seattle · Norwegian Cruise Line · Norwegian Bliss

7 May 2027 – 20 May 2027

£2,449

Route 66 Ultimate Road Trip and Adult Only Mexican Riviera Cruise - 24 Nights

Chicago · Virgin Voyages · Brilliant Lady

27 Oct 2027 – 21 Nov 2027

£3,659