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 10 May 15
 Return 12 May 15

Price subject to availability

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  • Dep date
  3 more CheapOair.com flights available on this route
$364   Dep 29 May 15 - Rtn 10 Jun 15
Chicago to San Juan
ORD to SJU CheapOair.com
$372   Dep 11 May 15 - Rtn 10 Jul 15
Chicago to San Juan
ORD to SJU CheapOair.com
$381   Dep 28 Apr 15 - Rtn 05 May 15
Chicago to San Juan
CHI to SJU CheapOair.com
Chicago (ORD) to Aguadilla (BQN)
 Depart 11 May 15
 Return 11 Jun 15

Flying with Spirit Airlines

Price subject to availability

 
 
Chicago (ORD) to Aguadilla (BQN)
 Depart 24 Jun 15
 Return 01 Jul 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
$618   Dep 08 Jul 15 - Rtn 15 Jul 15
Chicago to Aguadilla
ORD to BQN momondo.com
$632   Dep 01 Jul 15 - Rtn 08 Jul 15
Chicago to Aguadilla
ORD to BQN momondo.com
$645   Dep 22 Jul 15 - Rtn 29 Jul 15
Chicago to Aguadilla
ORD to BQN momondo.com
$651   Dep 15 Jul 15 - Rtn 22 Jul 15
Chicago to Aguadilla
ORD to BQN momondo.com
Chicago (ORD) to San Juan (SJU)
 Depart 11 May 15
 Return 13 May 15

Flying with United Airlines

Price subject to availability

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Chicago (CHI) to San Juan (SJU)
 Depart 13 May 15
 Return 20 May 15

Price subject to availability

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