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 21 Jan 17
 Return 01 Feb 17

Price subject to availability

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  • Price
  • Dep date
  15 more Smartfares.com flights available on this route
$319   Dep 28 Jan 17 - Rtn 06 Feb 17
Chicago to Aguadilla
ORD to BQN Smartfares.com
$334   Dep 20 Jan 17 - Rtn 14 Feb 17
Chicago to Ponce
ORD to PSE Smartfares.com
$350   Dep 13 Jan 17 - Rtn 17 Jan 17
Chicago to San Juan
ORD to SJU Smartfares.com
$351   Dep 20 Jan 17 - Rtn 14 Feb 17
Chicago to San Juan
ORD to SJU Smartfares.com
$374   Dep 14 Jan 17 - Rtn 21 Jan 17
Chicago to San Juan
ORD to SJU Smartfares.com
$391   Dep 10 Feb 17 - Rtn 12 Mar 17
Chicago to San Juan
ORD to SJU Smartfares.com
$396   Dep 22 Mar 17 - Rtn 26 Mar 17
Chicago to Ponce
ORD to PSE Smartfares.com
$406   Dep 12 Dec 16 - Rtn 22 Dec 16
Chicago to San Juan
ORD to SJU Smartfares.com
$410   Dep 21 Mar 17 - Rtn 26 Mar 17
Chicago to San Juan
ORD to SJU Smartfares.com
$448   Dep 22 Mar 17 - Rtn 26 Mar 17
Chicago to San Juan
ORD to SJU Smartfares.com
$461   Dep 07 Jan 17 - Rtn 23 Jan 17
Chicago to San Juan
ORD to SJU Smartfares.com
$466   Dep 10 Dec 16 - Rtn 13 Dec 16
Chicago to San Juan
ORD to SJU Smartfares.com
$647   Dep 21 Dec 16 - Rtn 28 Dec 16
Chicago to San Juan
ORD to SJU Smartfares.com
$734   Dep 23 Dec 16 - Rtn 27 Dec 16
Chicago to San Juan
ORD to SJU Smartfares.com
$754   Dep 22 Dec 16 - Rtn 27 Dec 16
Chicago to San Juan
ORD to SJU Smartfares.com
Chicago (CHI) to Aguadilla (BQN)
 Depart 21 Jan 17
 Return 24 Jan 17

Flying with JetBlue Airways

Price subject to availability

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  • Price
  • Dep date
  2 more OneTravel.com flights available on this route
$314   Dep 29 Jan 17 - Rtn 07 Feb 17
Chicago to Aguadilla
ORD to BQN OneTravel.com
$351   Dep 31 Jan 17 - Rtn 07 Feb 17
Chicago to Ponce
CHI to PSE OneTravel.com
Chicago (ORD) to San Juan (SJU)
 Depart 01 Feb 17
 Return 08 Feb 17

Flying with JetBlue Airways

Price subject to availability

 
 
Chicago (CHI) to San Juan (SJU)
 Depart 06 Jan 17
 Return 13 Jan 17

Price subject to availability

   View more dates
 
  • Price
  • Dep date
  13 more CheapAir.com flights available on this route
$341   Dep 07 Jan 17 - Rtn 14 Jan 17
Chicago to San Juan
CHI to SJU CheapAir.com
$390   Dep 17 Dec 16 - Rtn 24 Dec 16
Chicago to San Juan
CHI to SJU CheapAir.com
$423   Dep 09 Jan 17 - Rtn 16 Jan 17
Chicago to San Juan
CHI to SJU CheapAir.com
$484   Dep 31 Dec 16 - Rtn 07 Jan 17
Chicago to San Juan
CHI to SJU CheapAir.com
$488   Dep 04 Jan 17 - Rtn 11 Jan 17
Chicago to San Juan
CHI to SJU CheapAir.com
$515   Dep 19 Dec 16 - Rtn 26 Dec 16
Chicago to San Juan
CHI to SJU CheapAir.com
$603   Dep 21 Dec 16 - Rtn 28 Dec 16
Chicago to San Juan
CHI to SJU CheapAir.com
$623   Dep 30 Dec 16 - Rtn 06 Jan 17
Chicago to San Juan
CHI to SJU CheapAir.com
$645   Dep 24 Dec 16 - Rtn 31 Dec 16
Chicago to San Juan
CHI to SJU CheapAir.com
$645   Dep 02 Jan 17 - Rtn 09 Jan 17
Chicago to San Juan
CHI to SJU CheapAir.com
$791   Dep 28 Dec 16 - Rtn 04 Jan 17
Chicago to San Juan
CHI to SJU CheapAir.com
$811   Dep 23 Dec 16 - Rtn 30 Dec 16
Chicago to San Juan
CHI to SJU CheapAir.com
$1,229   Dep 26 Dec 16 - Rtn 02 Jan 17
Chicago to San Juan
CHI to SJU CheapAir.com
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