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 Aguadilla (BQN)
 Depart 10 Sep 16
 Return 20 Sep 16

Flying with Spirit Airlines

Price subject to availability

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  • Dep date
  4 more OneTravel.com flights available on this route
$352   Dep 21 Sep 16 - Rtn 17 Oct 16
Chicago to Aguadilla
ORD to BQN OneTravel.com
$434   Dep 19 Sep 16 - Rtn 19 Oct 16
Chicago to Ponce
CHI to PSE OneTravel.com
$455   Dep 17 Sep 16 - Rtn 20 Oct 16
Chicago to Ponce
ORD to PSE OneTravel.com
$470   Dep 12 Apr 17 - Rtn 18 Apr 17
Chicago to Mayaguez
CHI to MAZ OneTravel.com
Chicago (ORD) to San Juan (SJU)
 Depart 06 Oct 16
 Return 09 Oct 16

Price subject to availability

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Chicago (ORD) to San Juan (SJU)
 Depart 07 Sep 16
 Return 27 Sep 16

Flying with United Airlines

Price subject to availability

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  • Price
  • Dep date
  1 more CheapOair.com flights available on this route
$274   Dep 23 Sep 16 - Rtn 02 Oct 16
Chicago to San Juan
CHI to SJU CheapOair.com
Chicago (CHI) to San Juan (SJU)
 Depart 12 Sep 16
 Return 19 Sep 16

Price subject to availability

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