Cheap flights from Chicago to Caribbean

Travel > Caribbean

Travel tip: San Juan boasts numerous museums, hotels, historical buildings, beaches, restaurants and shopping centers. In San Juan there are a lot of attractions, for example: Ocean Park, Old San Juan, Isla Verde and Condado

Check our current prices for flights from Chicago to Caribbean. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Chicago to Caribbean, you will need to run a search below.

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From $351 / RT details

Book your flight now with Cheapoair.com and save!

Cheap St. Thomas Island airfares from $351/RT are provided by Cheapoair.com. Outbound flight is leaving on 07/31/2013, 05:30 am from Chicago O`hare (ORD) airport and arrives at St Thomas Island Cyril King (STT) at 03:31 pm. The flight time is 10 hours and 1 minutes. The Returning flight departes on 08/05/2013, 04:13 pm (other return dates are also available). Date posted: 01 Oct 2012

Price evolution for flights From Chicago To Caribbean

Price overview for flights from Chicago to Caribbean

Recent Deals on Flights from Chicago to Caribbean:Roundtrip / Oneway

  • $351Major Airline flight Major Airline 
    FromToDepartureTime
    Chicago, IL (ORD)St. Thomas Island, VI (STT)07/31/201305:30 am
    St. Thomas Island, VI (STT)Chicago, IL (ORD)08/05/201304:13 pm
    cheapoair.com check price
  • $372Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Nassau, BS (NAS)07/11/201305:30 am
    Nassau, BS (NAS)Chicago, IL (MDW)07/17/201305:22 pm
    cheapoair.com check price
  • $384Delta Airlines flight Delta Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Nassau, BS (NAS)07/11/201309:59 am
    Nassau, BS (NAS)Chicago, IL (MDW)07/17/201308:50 am
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  • $387United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/11/201309:35 pm
    Nassau, BS (NAS)Chicago, IL (ORD)07/17/201301:00 pm
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  • $390Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Nassau, BS (NAS)07/11/201305:30 am
    Nassau, BS (NAS)Chicago, IL (MDW)07/17/201305:22 pm
    faredepot.com check price
  • $400Delta Airlines flight Delta Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/11/201310:15 am
    Nassau, BS (NAS)Chicago, IL (ORD)07/17/201308:50 am
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  • $402Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)08/01/201307:10 am
    Hamilton, BM (BDA)Chicago, IL (MDW)08/16/201303:09 pm
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  • $402Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)07/24/201307:10 am
    Hamilton, BM (BDA)Chicago, IL (MDW)08/06/201303:09 pm
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  • $409Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)08/01/201306:52 pm
    Hamilton, BM (BDA)Chicago, IL (MDW)08/16/201303:09 pm
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  • $409Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)07/24/201305:40 am
    Hamilton, BM (BDA)Chicago, IL (MDW)08/06/201303:09 pm
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  • $409Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)08/01/201305:40 am
    Hamilton, BM (BDA)Chicago, IL (MDW)08/16/201303:09 pm
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  • $416Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)07/25/201308:52 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/08/201303:00 am
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  • $425Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)07/25/201308:52 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/08/201303:00 am
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  • $425Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)07/25/201308:52 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/08/201303:00 am
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  • $427United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)10/12/201304:00 pm
    Nassau, BS (NAS)Chicago, IL (ORD)10/19/201301:15 pm
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  • $428United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/11/201309:35 pm
    Nassau, BS (NAS)Chicago, IL (ORD)07/17/201303:17 pm
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  • $435United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)07/24/201309:35 pm
    Hamilton, BM (BDA)Chicago, IL (ORD)08/06/201303:45 pm
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  • $445American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/11/201305:30 am
    Nassau, BS (NAS)Chicago, IL (ORD)07/17/201303:50 pm
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  • $447Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)08/01/201307:45 am
    Hamilton, BM (BDA)Chicago, IL (ORD)08/16/201303:35 pm
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  • $449United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)08/01/201305:00 am
    Hamilton, BM (BDA)Chicago, IL (ORD)08/16/201303:45 pm
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  • $449American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)10/12/201307:25 pm
    Nassau, BS (NAS)Chicago, IL (ORD)10/19/201305:05 pm
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  • $450United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)07/24/201302:00 pm
    Hamilton, BM (BDA)Chicago, IL (ORD)08/06/201303:45 pm
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  • $450Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)07/24/201306:00 am
    Hamilton, BM (BDA)Chicago, IL (ORD)08/06/201303:35 pm
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  • $452United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)12/14/201305:00 am
    Nassau, BS (NAS)Chicago, IL (ORD)12/28/201301:50 pm
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  • $453American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)10/12/201307:00 am
    Nassau, BS (NAS)Chicago, IL (ORD)10/19/201305:05 pm
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  • $456Delta Airlines flight Delta Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)07/24/201304:50 pm
    Hamilton, BM (BDA)Chicago, IL (MDW)08/06/201303:54 pm
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  • $457United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)08/01/201309:35 pm
    Hamilton, BM (BDA)Chicago, IL (ORD)08/16/201303:45 pm
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  • $461United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)07/24/201309:35 pm
    Hamilton, BM (BDA)Chicago, IL (ORD)08/06/201303:45 pm
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  • $461United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)09/12/201302:00 pm
    Aguadilla, PR (BQN)Chicago, IL (ORD)09/21/201301:55 am
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  • $462Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aruba, AW (AUA)06/29/201305:30 am
    Aruba, AW (AUA)Chicago, IL (ORD)07/06/201303:05 pm
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  • $147Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Nassau, BS (NAS)07/04/201310:20 am
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  • $157Delta Airlines flight Delta Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Nassau, BS (NAS)07/04/201306:00 am
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  • $158United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/04/201301:05 pm
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  • $160American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/04/201306:00 am
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  • $164Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/04/201305:45 am
    faregeek.com check price
  • $165Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Nassau, BS (NAS)07/04/201310:20 am
    faredepot.com check price
  • $174Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)07/11/201307:10 am
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  • $178American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/04/201306:00 am
    faredepot.com check price
  • $182United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/04/201307:15 pm
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  • $184Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)07/11/201305:40 am
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  • $184Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Montego Bay, JM (MBJ)08/08/201308:52 pm
    cheapoair.com check price
  • $186Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)San Juan, PR (SJU)08/06/201306:45 am
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  • $207Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Montego Bay, JM (MBJ)08/08/201308:52 pm
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  • $215Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)07/04/201305:07 pm
    cheapoair.com check price
  • $220Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/06/201308:59 am
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  • $220Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)07/04/201305:07 pm
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  • $224Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/06/201308:59 am
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  • $228Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/04/201306:50 am
    cheapoair.com check price
  • $233Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)07/04/201305:07 pm
    faredepot.com check price
  • $234Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Montego Bay, JM (MBJ)08/08/201307:30 am
    cheapoair.com check price
  • $239Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/06/201305:30 am
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  • $246Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)St. Thomas Island, VI (STT)08/14/201307:30 am
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  • $246Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Montego Bay, JM (MBJ)08/08/201307:30 am
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  • $247Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Montego Bay, JM (MBJ)08/08/201309:04 pm
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  • $247United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/06/201303:25 pm
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  • $257Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)07/11/201307:45 am
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  • $258United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)07/11/201307:00 am
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  • $259United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)07/11/201303:25 pm
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  • $261Delta Airlines flight Delta Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)San Juan, PR (SJU)08/06/201309:18 am
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  • $261Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)07/19/201305:07 pm
    cheapoair.com check price
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Know what to do when flying to Caribbean?

San Juan Travel Guide Located in the Caribbean, in the Northern Coastal Plains of the island Puerto Rico, San Juan is the capital of this island. Known as "La Ciudad Amurallada" (the walled city), San Juan is an important port and also the oldest city in [...]
San Juan History San Juan, also known as “La Ciudad Amurallada”, occupies a land of 122 square kilometer and houses 442,447 inhabitants. The city is positioned in the Northern Coastal Plains and lying under the Karsts zone to the north of Caguas and [...]
San Juan Sightseeing Once you set foot on the soil of San Juan, you will feel as if you were taken back 500 years ago in 1508. In this city, you will experience firsthand what Latin American culture really is like. Though covered by a wall, San Juan never fails to [...]
San Juan Nightlife Like most cities, the San Juan night scene also comes alive during the weekends. Clubs, bars, discos and a lot more are to be found here. Whatever your action is, there is surely something for you in San Juan.  The majority of those who go out [...]
San Juan Pictures
  • El Morro - San Juanview
  • San Juan, Puerto Rico - San Juanview
  • San Juan, Puerto Rico - San Juanview
  • El Morro - San Juanview

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