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 19 Oct 15
 Return 22 Oct 15

Flying with JetBlue Airways

Price subject to availability

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  1 more CheapOair.com flights available on this route
$361   Dep 26 May 15 - Rtn 29 May 15
Chicago to San Juan
ORD to SJU CheapOair.com
Chicago (CHI) to San Juan (SJU)
 Depart 19 Apr 15
 Return 22 Apr 15

Flying with United Airlines

Price subject to availability

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Chicago (CHI) to San Juan (SJU)
 Depart 25 Apr 15
 Return 02 May 15

Price subject to availability

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Chicago (ORD) to Aguadilla (BQN)
 Depart 10 Jun 15
 Return 17 Jun 15

Flying with United Airlines

Price subject to availability

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  • Price
  • Dep date
  9 more momondo.com flights available on this route
$542   Dep 10 Jun 15 - Rtn 17 Jun 15
Chicago to Aguadilla
ORD to BQN momondo.com
$555   Dep 17 Jun 15 - Rtn 24 Jun 15
Chicago to Mayaguez
ORD to MAZ momondo.com
$561   Dep 17 Jun 15 - Rtn 24 Jun 15
Chicago to Aguadilla
ORD to BQN momondo.com
$615   Dep 24 Jun 15 - Rtn 01 Jul 15
Chicago to Aguadilla
ORD to BQN momondo.com
$616   Dep 17 Jun 15 - Rtn 24 Jun 15
Chicago to Aguadilla
ORD to BQN momondo.com
$744   Dep 27 May 15 - Rtn 03 Jun 15
Chicago to Aguadilla
ORD to BQN momondo.com
$784   Dep 03 Jun 15 - Rtn 10 Jun 15
Chicago to Aguadilla
ORD to BQN momondo.com
$909   Dep 27 May 15 - Rtn 03 Jun 15
Chicago to Aguadilla
ORD to BQN momondo.com
$1,011   Dep 03 Jun 15 - Rtn 10 Jun 15
Chicago to Aguadilla
ORD to BQN momondo.com
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