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 26 Aug 15
 Return 28 Aug 15

Price subject to availability

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  • Price
  • Dep date
  15 more CheapOair.com flights available on this route
$350   Dep 10 Sep 15 - Rtn 12 Sep 15
Chicago to San Juan
CHI to SJU CheapOair.com
$350   Dep 27 Oct 15 - Rtn 29 Oct 15
Chicago to San Juan
CHI to SJU CheapOair.com
$358   Dep 02 Sep 15 - Rtn 04 Sep 15
Chicago to San Juan
ORD to SJU CheapOair.com
$376   Dep 07 Nov 15 - Rtn 17 Nov 15
Chicago to San Juan
CHI to SJU CheapOair.com
$376   Dep 07 Nov 15 - Rtn 19 Nov 15
Chicago to San Juan
CHI to SJU CheapOair.com
$376   Dep 08 Nov 15 - Rtn 19 Nov 15
Chicago to San Juan
CHI to SJU CheapOair.com
$376   Dep 06 Dec 15 - Rtn 08 Dec 15
Chicago to San Juan
CHI to SJU CheapOair.com
$377   Dep 26 Aug 15 - Rtn 31 Aug 15
Chicago to San Juan
ORD to SJU CheapOair.com
$377   Dep 27 Aug 15 - Rtn 01 Sep 15
Chicago to San Juan
ORD to SJU CheapOair.com
$379   Dep 04 Nov 15 - Rtn 14 Nov 15
Chicago to San Juan
CHI to SJU CheapOair.com
$379   Dep 06 Nov 15 - Rtn 17 Nov 15
Chicago to San Juan
CHI to SJU CheapOair.com
$380   Dep 16 Aug 15 - Rtn 22 Aug 15
Chicago to San Juan
CHI to SJU CheapOair.com
$383   Dep 28 Aug 15 - Rtn 02 Sep 15
Chicago to San Juan
ORD to SJU CheapOair.com
$383   Dep 11 Aug 15 - Rtn 18 Aug 15
Chicago to San Juan
CHI to SJU CheapOair.com
$384   Dep 19 Nov 15 - Rtn 26 Nov 15
Chicago to San Juan
ORD to SJU CheapOair.com
Chicago (ORD) to Mayaguez (MAZ)
 Depart 28 Jul 15
 Return 26 Aug 15

Flying with United Airlines

Price subject to availability

 
 
Chicago (ORD) to Aguadilla (BQN)
 Depart 09 Sep 15
 Return 16 Sep 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
$497   Dep 16 Sep 15 - Rtn 23 Sep 15
Chicago to Aguadilla
ORD to BQN momondo.com
$504   Dep 23 Sep 15 - Rtn 30 Sep 15
Chicago to Aguadilla
ORD to BQN momondo.com
$527   Dep 07 Oct 15 - Rtn 14 Oct 15
Chicago to Aguadilla
ORD to BQN momondo.com
$535   Dep 30 Sep 15 - Rtn 07 Oct 15
Chicago to Aguadilla
ORD to BQN momondo.com
Chicago (ORD) to San Juan (SJU)
 Depart 18 Aug 15
 Return 02 Sep 15

Flying with JetBlue Airways

Price subject to availability

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Chicago (CHI) to San Juan (SJU)
 Depart 05 Aug 15
 Return 12 Aug 15

Price subject to availability

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