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 Oct 16
 Return 01 Nov 16

Price subject to availability

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  • Dep date
  15 more Smartfares.com flights available on this route
$238   Dep 26 Oct 16 - Rtn 03 Nov 16
Chicago to San Juan
ORD to SJU Smartfares.com
$238   Dep 30 Oct 16 - Rtn 04 Nov 16
Chicago to San Juan
ORD to SJU Smartfares.com
$238   Dep 31 Oct 16 - Rtn 03 Nov 16
Chicago to San Juan
ORD to SJU Smartfares.com
$238   Dep 01 Nov 16 - Rtn 08 Nov 16
Chicago to San Juan
ORD to SJU Smartfares.com
$238   Dep 01 Nov 16 - Rtn 09 Nov 16
Chicago to San Juan
ORD to SJU Smartfares.com
$238   Dep 02 Nov 16 - Rtn 08 Nov 16
Chicago to San Juan
ORD to SJU Smartfares.com
$238   Dep 02 Nov 16 - Rtn 09 Nov 16
Chicago to San Juan
ORD to SJU Smartfares.com
$238   Dep 13 Nov 16 - Rtn 16 Nov 16
Chicago to San Juan
ORD to SJU Smartfares.com
$258   Dep 09 Oct 16 - Rtn 14 Oct 16
Chicago to San Juan
ORD to SJU Smartfares.com
$258   Dep 09 Oct 16 - Rtn 28 Oct 16
Chicago to San Juan
ORD to SJU Smartfares.com
$258   Dep 11 Oct 16 - Rtn 20 Oct 16
Chicago to San Juan
ORD to SJU Smartfares.com
$258   Dep 12 Oct 16 - Rtn 20 Oct 16
Chicago to San Juan
ORD to SJU Smartfares.com
$268   Dep 01 Nov 16 - Rtn 24 Nov 16
Chicago to San Juan
ORD to SJU Smartfares.com
$268   Dep 16 Nov 16 - Rtn 24 Nov 16
Chicago to San Juan
ORD to SJU Smartfares.com
$278   Dep 08 Oct 16 - Rtn 12 Oct 16
Chicago to San Juan
ORD to SJU Smartfares.com
Chicago (CHI) to Aguadilla (BQN)
 Depart 01 Nov 16
 Return 09 Nov 16

Flying with United Airlines

Price subject to availability

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  • Dep date
  2 more OneTravel.com flights available on this route
$345   Dep 08 Feb 17 - Rtn 01 Mar 17
Chicago to Ponce
ORD to PSE OneTravel.com
$446   Dep 21 Oct 16 - Rtn 01 Nov 16
Chicago to Ponce
CHI to PSE OneTravel.com
Chicago (CHI) to San Juan (SJU)
 Depart 29 Oct 16
 Return 05 Nov 16

Price subject to availability

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  • Price
  • Dep date
  13 more CheapAir.com flights available on this route
$237   Dep 14 Oct 16 - Rtn 21 Oct 16
Chicago to San Juan
CHI to SJU CheapAir.com
$237   Dep 19 Oct 16 - Rtn 26 Oct 16
Chicago to San Juan
CHI to SJU CheapAir.com
$237   Dep 24 Oct 16 - Rtn 31 Oct 16
Chicago to San Juan
CHI to SJU CheapAir.com
$237   Dep 26 Oct 16 - Rtn 02 Nov 16
Chicago to San Juan
CHI to SJU CheapAir.com
$237   Dep 02 Nov 16 - Rtn 09 Nov 16
Chicago to San Juan
CHI to SJU CheapAir.com
$242   Dep 15 Oct 16 - Rtn 22 Oct 16
Chicago to San Juan
CHI to SJU CheapAir.com
$242   Dep 22 Oct 16 - Rtn 29 Oct 16
Chicago to San Juan
CHI to SJU CheapAir.com
$257   Dep 17 Oct 16 - Rtn 24 Oct 16
Chicago to San Juan
CHI to SJU CheapAir.com
$257   Dep 05 Nov 16 - Rtn 12 Nov 16
Chicago to San Juan
CHI to SJU CheapAir.com
$270   Dep 21 Oct 16 - Rtn 28 Oct 16
Chicago to San Juan
CHI to SJU CheapAir.com
$275   Dep 04 Nov 16 - Rtn 11 Nov 16
Chicago to San Juan
CHI to SJU CheapAir.com
$292   Dep 28 Oct 16 - Rtn 04 Nov 16
Chicago to San Juan
CHI to SJU CheapAir.com
$292   Dep 31 Oct 16 - Rtn 07 Nov 16
Chicago to San Juan
CHI to SJU CheapAir.com
Chicago (CHI) to San Juan (SJU)
 Depart 03 Oct 16
 Return 13 Oct 16

Flying with American Airlines

Price subject to availability

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  • Price
  • Dep date
  1 more CheapOair.com flights available on this route
$224   Dep 19 Oct 16 - Rtn 03 Nov 16
Chicago to San Juan
ORD to SJU CheapOair.com
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