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Cruises Calling at Chicago

80 upcoming cruises that stop at Chicago, Illinois, USA. Updated regularly; always confirm with the cruise line.

Victory 2
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 01 Aug 20269 nights11 portsDeparts 2026 Aug 01
$7299from / pp
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Victory 2
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 01 Aug 20269 nights14 portsDeparts 2026 Jul 23
$7299from / pp
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Victory 1
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 03 Aug 20269 nights11 portsDeparts 2026 Aug 03
$7299from / pp
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Victory 1
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 03 Aug 20269 nights14 portsDeparts 2026 Jul 25
$7299from / pp
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Victory 2
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 19 Aug 20269 nights14 portsDeparts 2026 Aug 10
$7299from / pp
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Victory 2
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 19 Aug 20269 nights11 portsDeparts 2026 Aug 19
$7299from / pp
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Victory 1
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 21 Aug 20269 nights14 portsDeparts 2026 Aug 12
$7299from / pp
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Victory 1
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 21 Aug 20269 nights11 portsDeparts 2026 Aug 21
$7299from / pp
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Victory 2
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 06 Sep 20269 nights14 portsDeparts 2026 Aug 28
$7899from / pp
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Victory 2
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 06 Sep 20269 nights11 portsDeparts 2026 Sep 06
$7899from / pp
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Victory 1
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 08 Sep 20269 nights14 portsDeparts 2026 Aug 30
$7899from / pp
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Victory 1
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 08 Sep 20269 nights11 portsDeparts 2026 Sep 08
$7899from / pp
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Viking Octantis
Viking Cruises
Toronto → Milwaukee WI
⚓ Calls 22 Sep 202616 nights15 portsDeparts 2026 Sep 07
Price on request
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Viking Octantis
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 22 Sep 20269 nights9 portsDeparts 2026 Sep 14
Price on request
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Victory 2
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 24 Sep 20269 nights14 portsDeparts 2026 Sep 15
$7899from / pp
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Victory 2
American Queen Voyages Cruises
Chicago → Quebec City
⚓ Calls 24 Sep 202612 nights15 portsDeparts 2026 Sep 24
$9499from / pp
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Victory 1
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 26 Sep 20269 nights14 portsDeparts 2026 Sep 17
$7899from / pp
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Victory 1
American Queen Voyages Cruises
Chicago → Montreal
⚓ Calls 26 Sep 202611 nights14 portsDeparts 2026 Sep 26
$7999from / pp
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Viking Octantis
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 01 Oct 20269 nights9 portsDeparts 2026 Sep 23
Price on request
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Viking Octantis
Viking Cruises
Milwaukee WI → Toronto
⚓ Calls 01 Oct 202616 nights15 portsDeparts 2026 Sep 23
Price on request
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Victory 1
American Queen Voyages Cruises
Montreal → Chicago
⚓ Calls 18 Oct 202611 nights14 portsDeparts 2026 Oct 07
$7999from / pp
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Victory 1
American Queen Voyages Cruises
Chicago → Montreal
⚓ Calls 18 Oct 202611 nights14 portsDeparts 2026 Oct 18
$7999from / pp
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Victory 2
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 13 May 20279 nights14 portsDeparts 2027 May 04
$6799from / pp
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Victory 2
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 13 May 20279 nights13 portsDeparts 2027 May 13
$6799from / pp
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Viking Polaris
Viking Cruises
Toronto → Milwaukee WI
⚓ Calls 21 May 202716 nights15 portsDeparts 2027 May 06
$20490from / pp
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Viking Polaris
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 21 May 20279 nights9 portsDeparts 2027 May 13
$10995from / pp
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Victory 1
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 25 May 20279 nights14 portsDeparts 2027 May 16
$6799from / pp
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Victory 1
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 25 May 20279 nights13 portsDeparts 2027 May 25
$6799from / pp
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Viking Polaris
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 30 May 20279 nights9 portsDeparts 2027 May 22
$11695from / pp
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Viking Polaris
Viking Cruises
Milwaukee WI → Toronto
⚓ Calls 30 May 202716 nights15 portsDeparts 2027 May 22
$21490from / pp
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Victory 2
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 31 May 20279 nights14 portsDeparts 2027 May 22
$6799from / pp
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Victory 2
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 31 May 20279 nights13 portsDeparts 2027 May 31
$7499from / pp
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Victory 1
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 12 Jun 20279 nights14 portsDeparts 2027 Jun 03
$7499from / pp
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Victory 1
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 12 Jun 20279 nights13 portsDeparts 2027 Jun 12
$7499from / pp
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Victory 2
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 18 Jun 20279 nights14 portsDeparts 2027 Jun 09
$7499from / pp
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Victory 2
American Queen Voyages Cruises
Round-trip from Chicago
⚓ Calls 18 Jun 202714 nights16 portsDeparts 2027 Jun 18
$9899from / pp
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Victory 1
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 30 Jun 20279 nights14 portsDeparts 2027 Jun 21
$7499from / pp
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Victory 1
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 30 Jun 20279 nights13 portsDeparts 2027 Jun 30
$7499from / pp
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Victory 2
American Queen Voyages Cruises
Round-trip from Chicago
⚓ Calls 02 Jul 202714 nights16 portsDeparts 2027 Jul 02
$9899from / pp
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Victory 2
American Queen Voyages Cruises
Chicago → Quebec City
⚓ Calls 16 Jul 202712 nights15 portsDeparts 2027 Jul 16
$9899from / pp
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Victory 1
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 18 Jul 20279 nights14 portsDeparts 2027 Jul 09
$7499from / pp
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Victory 1
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 18 Jul 20279 nights13 portsDeparts 2027 Jul 18
$7499from / pp
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Victory 1
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 05 Aug 20279 nights13 portsDeparts 2027 Aug 05
$7499from / pp
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Victory 1
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 05 Aug 20279 nights14 portsDeparts 2027 Jul 27
$7499from / pp
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Victory 1
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 23 Aug 20279 nights14 portsDeparts 2027 Aug 14
$7499from / pp
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Victory 1
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 23 Aug 20279 nights13 portsDeparts 2027 Aug 23
$7499from / pp
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Viking Polaris
Viking Cruises
Toronto → Milwaukee WI
⚓ Calls 31 Aug 202716 nights15 portsDeparts 2027 Aug 16
$21490from / pp
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Viking Polaris
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 31 Aug 20279 nights9 portsDeparts 2027 Aug 23
$11495from / pp
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Victory 2
American Queen Voyages Cruises
Chicago → Toronto
⚓ Calls 02 Sep 20279 nights13 portsDeparts 2027 Sep 02
$8099from / pp
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Viking Polaris
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 09 Sep 20279 nights9 portsDeparts 2027 Sep 01
$12195from / pp
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Viking Polaris
Viking Cruises
Milwaukee WI → Toronto
⚓ Calls 09 Sep 202716 nights15 portsDeparts 2027 Sep 01
$22290from / pp
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Victory 1
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 10 Sep 20279 nights14 portsDeparts 2027 Sep 01
$8099from / pp
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Victory 1
American Queen Voyages Cruises
Chicago → Montreal
⚓ Calls 10 Sep 202711 nights14 portsDeparts 2027 Sep 10
$8299from / pp
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Victory 2
American Queen Voyages Cruises
Toronto → Chicago
⚓ Calls 20 Sep 20279 nights14 portsDeparts 2027 Sep 11
$8099from / pp
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Viking Octantis
Viking Cruises
Toronto → Milwaukee WI
⚓ Calls 24 May 202816 nights15 portsDeparts 2028 May 09
$17790from / pp
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Viking Octantis
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 24 May 20289 nights9 portsDeparts 2028 May 16
$9995from / pp
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Viking Octantis
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 02 Jun 20289 nights9 portsDeparts 2028 May 25
$9995from / pp
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Viking Octantis
Viking Cruises
Milwaukee WI → Toronto
⚓ Calls 02 Jun 202816 nights15 portsDeparts 2028 May 25
$18490from / pp
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Viking Octantis
Viking Cruises
Toronto → Milwaukee WI
⚓ Calls 23 Jul 202816 nights15 portsDeparts 2028 Jul 08
$17990from / pp
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Viking Octantis
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 23 Jul 20289 nights9 portsDeparts 2028 Jul 15
$9995from / pp
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Viking Octantis
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 01 Aug 20289 nights9 portsDeparts 2028 Jul 24
$9995from / pp
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Viking Octantis
Viking Cruises
Milwaukee WI → Toronto
⚓ Calls 01 Aug 202816 nights14 portsDeparts 2028 Jul 24
$17990from / pp
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Viking Octantis
Viking Cruises
Toronto → Milwaukee WI
⚓ Calls 21 Sep 202816 nights15 portsDeparts 2028 Sep 06
$19990from / pp
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Viking Octantis
Viking Cruises
Milwaukee WI → Toronto
⚓ Calls 21 Sep 202816 nights15 portsDeparts 2028 Sep 13
$19990from / pp
Check fares
Viking Octantis
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 21 Sep 20289 nights9 portsDeparts 2028 Sep 13
$10995from / pp
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Viking Polaris
Viking Cruises
Toronto → Milwaukee WI
⚓ Calls 26 May 202916 nights15 portsDeparts 2029 May 11
$16498from / pp
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Viking Polaris
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 26 May 20299 nights9 portsDeparts 2029 May 18
$8999from / pp
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Viking Octantis
Viking Cruises
Toronto → Milwaukee WI
⚓ Calls 28 May 202916 nights15 portsDeparts 2029 May 13
$16498from / pp
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Viking Octantis
Viking Cruises
Milwaukee WI → Toronto
⚓ Calls 28 May 202916 nights15 portsDeparts 2029 May 20
$16498from / pp
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Viking Octantis
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 28 May 20299 nights9 portsDeparts 2029 May 20
$8999from / pp
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Viking Polaris
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 04 Jun 20299 nights9 portsDeparts 2029 May 27
$9599from / pp
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Viking Polaris
Viking Cruises
Milwaukee WI → Toronto
⚓ Calls 04 Jun 202916 nights15 portsDeparts 2029 May 27
$17098from / pp
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Viking Polaris
Viking Cruises
Toronto → Milwaukee WI
⚓ Calls 27 Jun 202916 nights15 portsDeparts 2029 Jun 12
$17098from / pp
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Viking Polaris
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 27 Jun 20299 nights9 portsDeparts 2029 Jun 19
$9599from / pp
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Viking Polaris
Viking Cruises
Milwaukee WI → Toronto
⚓ Calls 06 Jul 202916 nights15 portsDeparts 2029 Jun 28
$17598from / pp
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Viking Polaris
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 06 Jul 20299 nights9 portsDeparts 2029 Jun 28
$9599from / pp
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Viking Polaris
Viking Cruises
Toronto → Milwaukee WI
⚓ Calls 29 Jul 202916 nights15 portsDeparts 2029 Jul 14
$17998from / pp
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Viking Polaris
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 29 Jul 20299 nights9 portsDeparts 2029 Jul 21
$9999from / pp
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Viking Polaris
Viking Cruises
Round-trip from Milwaukee WI
⚓ Calls 07 Aug 20299 nights9 portsDeparts 2029 Jul 30
$9999from / pp
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Viking Polaris
Viking Cruises
Milwaukee WI → Toronto
⚓ Calls 07 Aug 202916 nights15 portsDeparts 2029 Jul 30
$17998from / pp
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Itineraries and prices change — always confirm with the cruise line before booking. Some links are affiliate links that may earn us a commission at no extra cost to you.