Chicago cruises

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

5 on sale

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

Ketchikan · MSC Cruises · MSC Poesia

25 Apr 2027 – 8 May 2027

£2,299

Alaska & Rockies Express to Chicago All-Inclusive Cruise

Seattle · Norwegian Cruise Line · Norwegian Bliss

8 Oct 2027 – 21 Oct 2027

£2,399

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

Chicago · Royal Caribbean · Quantum of the Seas

5 May 2027 – 18 May 2027

£2,449

Route 66 Fly Drive and All Inclusive Mexican Riviera Cruise - 22 Nights

Chicago · Norwegian Cruise Line · Norwegian Encore

21 Nov 2026 – 14 Dec 2026

£3,489

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

Chicago · Virgin Voyages · Brilliant Lady

25 Mar 2027 – 19 Apr 2027

£3,659