Flights from Chicago (CHI) to Puerto Rico (Puerto Rico)

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We compare hundreds of flights from Chicago to Puerto Rico from a range of airlines and travel agents to get you the best deals. Find cheap flights along this route.
Chicago (CHI) to San Juan (SJU)
 Depart 16 Sep 15
 Return 20 Sep 15

Price subject to availability

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  • Price
  • Dep date
  15 more CheapOair.com flights available on this route
$366   Dep 03 Nov 15 - Rtn 09 Nov 15
Chicago to San Juan
CHI to SJU CheapOair.com
$369   Dep 31 Oct 15 - Rtn 09 Nov 15
Chicago to San Juan
ORD to SJU CheapOair.com
$369   Dep 01 Nov 15 - Rtn 09 Nov 15
Chicago to San Juan
ORD to SJU CheapOair.com
$369   Dep 04 Nov 15 - Rtn 12 Nov 15
Chicago to San Juan
ORD to SJU CheapOair.com
$370   Dep 11 Aug 15 - Rtn 18 Aug 15
Chicago to San Juan
CHI to SJU CheapOair.com
$370   Dep 19 Aug 15 - Rtn 03 Sep 15
Chicago to San Juan
CHI to SJU CheapOair.com
$370   Dep 26 Aug 15 - Rtn 02 Sep 15
Chicago to San Juan
CHI to SJU CheapOair.com
$386   Dep 07 Jul 15 - Rtn 21 Jul 15
Chicago to San Juan
CHI to SJU CheapOair.com
$397   Dep 02 Jul 15 - Rtn 04 Jul 15
Chicago to San Juan
CHI to SJU CheapOair.com
$398   Dep 05 Jun 15 - Rtn 12 Jun 15
Chicago to San Juan
CHI to SJU CheapOair.com
$413   Dep 17 Jul 15 - Rtn 23 Jul 15
Chicago to San Juan
CHI to SJU CheapOair.com
$425   Dep 01 Jun 15 - Rtn 06 Jun 15
Chicago to San Juan
CHI to SJU CheapOair.com
$425   Dep 04 Jul 15 - Rtn 12 Jul 15
Chicago to San Juan
CHI to SJU CheapOair.com
$428   Dep 10 Jul 15 - Rtn 19 Jul 15
Chicago to San Juan
CHI to SJU CheapOair.com
$429   Dep 03 Jun 15 - Rtn 10 Jun 15
Chicago to San Juan
CHI to SJU CheapOair.com
Chicago (CHI) to San Juan (SJU)
 Depart 13 Jun 15
 Return 20 Jun 15

Price subject to availability

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Chicago (ORD) to San Juan (SJU)
 Depart 19 Aug 15
 Return 02 Sep 15

Flying with US Airways

Price subject to availability

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Chicago (CHI) to Aguadilla (BQN)
 Depart 28 Jun 15
 Return 30 Jun 15

Price subject to availability

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  • Price
  • Dep date
  1 more OneTravel.com flights available on this route
$599   Dep 19 Jun 15 - Rtn 17 Jul 15
Chicago to Mayaguez
ORD to MAZ OneTravel.com
Chicago (ORD) to Aguadilla (BQN)
 Depart 19 Aug 15
 Return 26 Aug 15

Flying with JetBlue Airways

Price subject to availability

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  • Price
  • Dep date
  4 more momondo.com flights available on this route
$662   Dep 29 Jul 15 - Rtn 05 Aug 15
Chicago to Aguadilla
ORD to BQN momondo.com
$669   Dep 26 Aug 15 - Rtn 02 Sep 15
Chicago to Aguadilla
ORD to BQN momondo.com
$684   Dep 12 Aug 15 - Rtn 19 Aug 15
Chicago to Aguadilla
ORD to BQN momondo.com
$707   Dep 05 Aug 15 - Rtn 12 Aug 15
Chicago to Aguadilla
ORD to BQN momondo.com
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