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 (ORD) to San Juan (SJU)
 Depart 22 Aug 16
 Return 02 Sep 16

Flying with JetBlue Airways

Price subject to availability

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  • Dep date
  1 more CheapOair.com flights available on this route
$298   Dep 23 Aug 16 - Rtn 06 Sep 16
Chicago to San Juan
CHI to SJU CheapOair.com
Chicago (CHI) to Aguadilla (BQN)
 Depart 24 Aug 16
 Return 04 Sep 16

Flying with Spirit Airlines

Price subject to availability

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  • Price
  • Dep date
  3 more OneTravel.com flights available on this route
$351   Dep 13 Jul 16 - Rtn 09 Aug 16
Chicago to Aguadilla
ORD to BQN OneTravel.com
$504   Dep 15 Jul 16 - Rtn 11 Aug 16
Chicago to Mayaguez
ORD to MAZ OneTravel.com
$557   Dep 14 Jul 16 - Rtn 10 Aug 16
Chicago to Ponce
ORD to PSE OneTravel.com
Chicago (ORD) to San Juan (SJU)
 Depart 13 Oct 16
 Return 20 Oct 16

Price subject to availability

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Chicago (CHI) to San Juan (SJU)
 Depart 22 Jul 16
 Return 29 Jul 16

Price subject to availability

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