Chicago

Cruise & Stay

WELCOME TO CHICAGO

Chicago is the third biggest city in the USA based on population. It's therefore unsurprising that there are a multitude of things to see and do in "The Windy City". 

Located on the shores on Lake Michigan, Chicago is the home to some of the best restaurants, nightlife, shopping and museums the US has to offer. 

Cruise Deals departing in
Departure What's Included? Price (From)

15nt Music Cities & Caribbean from New Orleans

Norwegian Getaway | 15 nights

28 Nov 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
  • Free Upgrade to Oceanview Cabin
£1299 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

12 May 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1369 View Deal

10nt Alaska with Chicago & Seattle Stays

Norwegian Bliss | 10 nights

02 May 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
£1449 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

29 Apr 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1499 View Deal

15nt Chicago, Memphis, New Orleans & Caribbean

Carnival Glory | 15 nights

05 Oct 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • FREE City Tour Included
£1529 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

06 May 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1529 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

27 May 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1549 View Deal

15nt Chicago, Memphis, New Orleans & Caribbean

Carnival Glory | 15 nights

30 Nov 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • FREE City Tour Included
£1549 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

29 Apr 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
  • FREE Upgrade from Outside to Balcony
£1549 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

13 May 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1549 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

26 May 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1579 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

13 May 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1579 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

02 Sep 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1599 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

01 Sep 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1599 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

16 Sep 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1599 View Deal

15nt Chicago, Memphis, New Orleans & Caribbean

Carnival Glory | 15 nights

07 Sep 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • FREE City Tour Included
£1599 View Deal

15nt Chicago, Memphis, New Orleans & Caribbean

Carnival Glory | 15 nights

21 Sep 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • FREE City Tour Included
£1599 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

06 May 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1599 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

09 Sep 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1629 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

25 Aug 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1629 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

19 May 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1649 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

20 May 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1699 View Deal

18nt Vancouver, Alaska & Empire Builder to Chicago

Carnival Legend | 18 nights

27 Apr 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1699 View Deal

15nts Chicago, Memphis & New Orleans Glory

Carnival Glory | 15 nights

12 Sep 20
  • FREE centrally located handpicked hotel stay
  • Flights Included
£1699 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

16 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1719 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

23 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1729 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

20 May 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1729 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

09 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1749 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

26 Aug 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1779 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

02 Sep 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1799 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

02 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1799 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

30 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1799 View Deal

15nt Chicago, Memphis, New Orleans & Caribbean

Carnival Glory | 15 nights

15 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • FREE City Tour Included
£1799 View Deal

Chicago, Builder Train, Seattle, Alaska, Vancouver

Ruby Princess | 15 nights

08 Sep 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1819 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

03 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1829 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

03 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1829 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

27 May 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1829 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

17 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1849 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

10 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1869 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

24 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1869 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

18 Aug 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1869 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

11 May 20
  • Amtrak Rail Included
£1869 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

24 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1899 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

12 Aug 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1899 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

04 May 20
  • Amtrak Rail Included
£1899 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

07 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1919 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

01 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1929 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

01 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1949 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

26 Aug 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1949 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

09 Sep 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1949 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

14 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1949 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

04 Aug 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1949 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

11 Aug 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1949 View Deal

15nt Chicago, Memphis, New Orleans & Caribbean

Carnival Glory | 15 nights

13 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • FREE City Tour Included
£1949 View Deal

15nt Chicago, Memphis, New Orleans & Caribbean

Carnival Glory | 15 nights

17 Oct 20
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • FREE City Tour Included
£1949 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

17 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1969 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

19 Aug 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£1969 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

25 May 20
  • Amtrak Rail Included
£1969 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

14 Sep 20
  • Amtrak Rail Included
£1969 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

28 Sep 20
  • Amtrak Rail Included
£1969 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

28 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£1999 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

31 Aug 20
  • Amtrak Rail Included
£1999 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

07 Sep 20
  • Amtrak Rail Included
£1999 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

19 Aug 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£2029 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

10 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£2049 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

05 Aug 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£2049 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

16 Sep 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£2049 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Ruby Princess | 13 nights

21 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£2049 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

18 May 20
  • Amtrak Rail Included
£2049 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

01 Jun 20
  • Amtrak Rail Included
£2049 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

12 Aug 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£2069 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

08 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£2099 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

08 Jun 20
  • Amtrak Rail Included
£2099 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

22 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£2119 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

29 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£2129 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

21 Sep 20
  • Amtrak Rail Included
£2129 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

22 Jun 20
  • Amtrak Rail Included
£2149 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

15 Jun 20
  • Amtrak Rail Included
£2169 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

15 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£2199 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

15 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£2199 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

29 Jun 20
  • Amtrak Rail Included
£2199 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

22 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£2249 View Deal

15nt Chicago, Memphis, New Orleans & Caribbean

Carnival Glory | 15 nights

29 Jun 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • FREE City Tour Included
£2249 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

24 Aug 20
  • Amtrak Rail Included
£2269 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

05 Aug 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£2269 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

29 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Brand New Ship!
£2279 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

20 Jul 20
  • Amtrak Rail Included
£2299 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

10 Aug 20
  • Amtrak Rail Included
£2299 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

17 Aug 20
  • Amtrak Rail Included
£2299 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

06 Jul 20
  • Amtrak Rail Included
£2329 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Oosterdam | 13 nights

08 Jul 19
  • FREE centrally located handpicked hotel stay
  • Flights Included
  • Amtrak Rail Included
£2349 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

13 Jul 20
  • Amtrak Rail Included
£2349 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

27 Jul 20
  • Amtrak Rail Included
£2349 View Deal

Chicago, Empire Builder Train, Seattle & Alaska

Norwegian Bliss | 13 nights

03 Aug 20
  • Amtrak Rail Included
£2369 View Deal
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