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 $330 / RT details

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Cheap Montego Bay airfares from $330/RT are provided by FlightHub. Outbound flight is leaving on 12/01/2014, 04:00 pm from Chicago O`hare (ORD) airport and arrives at Montego Bay Sangster (MBJ) at 11:46 am. The flight time is 19 hours and 46 minutes. The Returning flight departes on 12/05/2014, 01:45 pm (other return dates are also available). Date posted: 13 Oct 2014

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

  • $330Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Montego Bay, JM (MBJ)12/01/201404:00 pm
    Montego Bay, JM (MBJ)Chicago, IL (ORD)12/05/201401:45 pm
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  • $339Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Montego Bay, JM (MBJ)12/01/201410:05 pm
    Montego Bay, JM (MBJ)Chicago, IL (ORD)12/05/201401:45 pm
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  • $345Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)07/15/201508:30 am
    San Juan, PR (SJU)Chicago, IL (ORD)07/25/201505:40 pm
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  • $345Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)07/15/201508:30 am
    San Juan, PR (SJU)Chicago, IL (ORD)07/25/201505:40 pm
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  • $349Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Montego Bay, JM (MBJ)12/01/201406:25 pm
    Montego Bay, JM (MBJ)Chicago, IL (ORD)12/05/201401:45 pm
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  • $140Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)10/24/201405:15 am
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  • $142Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)10/24/201405:15 am
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  • $149Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)10/24/201409:00 am
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  • $149Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)11/01/201408:30 am
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  • $151Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)10/24/201409:00 am
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cheap domestic and international flights

Recently found cheap flight deals

South African AirwaysToronto To Cape Town South African Airways airfares from Toronto in December
$4686 Depart: 12/19/2014
Return: 01/02/2015

provided by FlightHub

Air CanadaWindsor To San Jose Air Canada airfares from Windsor in December
$1464 Depart: 12/20/2014
Return: 01/06/2015

provided by FlightHub

US AirwaysChicago To Greensboro US Airways airfares from Chicago in November
$333 Depart: 11/05/2014
Return: 11/16/2014

provided by FlightHub

Multiple AirlinesPhoenix To Sarajevo Multiple Airlines airfares from Phoenix in July
$1876 Depart: 07/02/2014
Return: 07/15/2014

provided by Expedia

United AirlinesSan Jose To Dallas United Airlines airfares from San Jose in November
$485 Depart: 11/22/2014
Return: 11/29/2014

provided by FlightHub

US AirwaysBurlington To Orlando US Airways airfares from Burlington in October
$498 Depart: 10/30/2014
Return: 11/02/2014

provided by FlightHub

American AirlinesDallas To Louisville American Airlines airfares from Dallas in November
$361 Depart: 11/18/2014
Return: 12/02/2014

provided by FlightHub

LufthansaLos Angeles To Malaga Lufthansa airfares from Los Angeles in October
$1221 Depart: 10/07/2014
Return: 10/22/2014

provided by FlightHub

US AirwaysLos Angeles To Sacramento US Airways airfares from Los Angeles in November
$522 Depart: 11/25/2014
Return: 12/03/2014

provided by FlightHub

 

Specify your search details. Browse the cheapest flights from Chicago to Caribbean, Caribbean hotel rooms and Chicago to Caribbean vacation packages from the most popular providers, airline consolidators and travel search engines.

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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