Illinois to Caribbean flights

74 flights from 8 advertisers. Deals are automatically sorted by most popular.
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Chicago (CHI) to San Juan (SJU)
 Depart 12 Jun 12
 Return 19 Jun 12

Price subject to availability

 
 
$383 RT incl. taxes Go to website
Chicago (ORD) to San Jose (SJO)
 Depart 13 Jun 12
 Return 20 Jun 12

Flying with COPA

Price subject to availability

 
 
$522 RT incl. taxes Go to website
 
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5 more Expedia flights available on this route
$543   Dep 13 Jun 12 - Rtn 20 Jun 12 Chicago to San Jose ORD to SJO Expedia  Web
$651   Dep 15 Jun 12 - Rtn 22 Jun 12 Chicago to San Jose ORD to SJO Expedia  Web
$698   Dep 13 Jun 12 - Rtn 20 Jun 12 Chicago to San Jose ORD to SJO Expedia  Web
$768   Dep 15 Jun 12 - Rtn 22 Jun 12 Chicago to Montego Bay MDW to MBJ Expedia  Web
$801   Dep 13 Jun 12 - Rtn 20 Jun 12 Chicago to Montego Bay MDW to MBJ Expedia  Web
Fares include taxes.  Subject to availability.  Updated 20 hours ago.  
Chicago (ORD) to San Juan (SJU)
 Depart 03 Jul 12
 Return 10 Jul 12

Price subject to availability

 
 
$466 RT incl. taxes Go to website
Chicago (CHI) to Nassau (NAS)
 Depart 04 Jul 12
 Return 11 Jul 12

Price subject to availability

 
 
$363 RT incl. taxes Go to website
 
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Chicago (ORD) to San Jose (SJO)
 Depart 13 Jun 12
 Return 20 Jun 12

Cheapest Student Airfares Guaranteed!

Price subject to availability

 
 
$566 RT incl. taxes Go to website
 
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0 more STA Student Travel flights available on this route
Fares include taxes.  Subject to availability.  Updated 22 hours ago.  
Chicago (ORD) to San Jose (SJO)
 Depart 23 Jul 12
 Return 30 Jul 12

Flying with Major US Carrier

Price subject to availability

 
 
$562 RT incl. taxes Go to website
 
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0 more StudentUniverse flights available on this route
Fares include taxes.  Subject to availability.  Updated 22 hours ago.  
Chicago (ORD) to San Pedro Sula (SAP)
 Depart 20 Jun 12
 Return 27 Jun 12

Flying with Spirit Airlines

Price subject to availability

 
 
$429 RT incl. taxes Go to website
 
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0 more Orbitz flights available on this route
Fares include taxes.  Subject to availability.  Updated 10 hours ago.  
Chicago (ORD) to San Juan (SJU)
 Depart 02 Jun 12
 Return 12 Jun 12

Price subject to availability

 
 
$303 RT incl. taxes Go to website
 
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0 more Hotwire flights available on this route
Fares include taxes.  Subject to availability.  Updated 14 hours ago.  
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