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 Aguadilla (BQN)
 Depart 19 Aug 15
 Return 03 Sep 15

Flying with Spirit Airlines

Price subject to availability

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  • Price
  • Dep date
  3 more OneTravel.com flights available on this route
$410   Dep 19 Aug 15 - Rtn 18 Sep 15
Chicago to Mayaguez
ORD to MAZ OneTravel.com
$428   Dep 28 Aug 15 - Rtn 30 Aug 15
Chicago to Ponce
CHI to PSE OneTravel.com
$458   Dep 19 Aug 15 - Rtn 16 Sep 15
Chicago to Ponce
ORD to PSE OneTravel.com
Chicago (CHI) to San Juan (SJU)
 Depart 26 Aug 15
 Return 02 Sep 15

Price subject to availability

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Chicago (CHI) to San Juan (SJU)
 Depart 30 Aug 15
 Return 06 Sep 15

Price subject to availability

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  • Price
  • Dep date
  15 more CheapOair.com flights available on this route
$316   Dep 30 Aug 15 - Rtn 13 Sep 15
Chicago to San Juan
CHI to SJU CheapOair.com
$316   Dep 21 Oct 15 - Rtn 28 Oct 15
Chicago to San Juan
CHI to SJU CheapOair.com
$324   Dep 10 Nov 15 - Rtn 12 Nov 15
Chicago to San Juan
ORD to SJU CheapOair.com
$346   Dep 16 Nov 15 - Rtn 21 Nov 15
Chicago to San Juan
CHI to SJU CheapOair.com
$346   Dep 18 Jan 16 - Rtn 20 Jan 16
Chicago to San Juan
CHI to SJU CheapOair.com
$354   Dep 31 Aug 15 - Rtn 04 Sep 15
Chicago to San Juan
ORD to SJU CheapOair.com
$354   Dep 01 Sep 15 - Rtn 04 Sep 15
Chicago to San Juan
ORD to SJU CheapOair.com
$354   Dep 02 Sep 15 - Rtn 04 Sep 15
Chicago to San Juan
ORD to SJU CheapOair.com
$354   Dep 09 Nov 15 - Rtn 13 Nov 15
Chicago to San Juan
ORD to SJU CheapOair.com
$354   Dep 10 Nov 15 - Rtn 16 Nov 15
Chicago to San Juan
ORD to SJU CheapOair.com
$356   Dep 11 Nov 15 - Rtn 13 Nov 15
Chicago to San Juan
CHI to SJU CheapOair.com
$362   Dep 24 Oct 15 - Rtn 01 Nov 15
Chicago to San Juan
CHI to SJU CheapOair.com
$365   Dep 03 Sep 15 - Rtn 05 Sep 15
Chicago to San Juan
CHI to SJU CheapOair.com
$374   Dep 11 Nov 15 - Rtn 15 Nov 15
Chicago to San Juan
CHI to SJU CheapOair.com
$375   Dep 12 Aug 15 - Rtn 23 Aug 15
Chicago to San Juan
CHI to SJU CheapOair.com
Chicago (ORD) to Aguadilla (BQN)
 Depart 21 Oct 15
 Return 28 Oct 15

Flying with JetBlue Airways

Price subject to availability

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  • Price
  • Dep date
  7 more momondo.com flights available on this route
$498   Dep 14 Oct 15 - Rtn 21 Oct 15
Chicago to Aguadilla
ORD to BQN momondo.com
$500   Dep 28 Oct 15 - Rtn 04 Nov 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
$795   Dep 28 Oct 15 - Rtn 04 Nov 15
Chicago to Aguadilla
ORD to BQN momondo.com
$878   Dep 21 Oct 15 - Rtn 28 Oct 15
Chicago to Aguadilla
ORD to BQN momondo.com
Chicago (CHI) to San Juan (SJU)
 Depart 18 Aug 15
 Return 02 Sep 15

Flying with JetBlue Airways

Price subject to availability

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