Cheap flights from Illinois to Caribbean

Travel > Caribbean

The place to head for complete relaxation for your next vacation is none other than Montego Bay, Jamaica. Montego Bay is a hot tourist spot, and has been such since 1924. And as proof of this increased tourism in Montego Bay, you find a bustling community here at all times.... (read more in our Montego Bay Sightseeing)

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Cheapest flights found for the next 6 months

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Check our newest flight offers to Caribbean:

  • $348Aeromexico flight Aeromexico 
    Chicago, IL (ORD)Santo Domingo, DO (SDQ)08/18/201607:00 am
    Santo Domingo, DO (SDQ)Chicago, IL (ORD)08/22/201608:41 am check price
  • $363United Airlines flight United Airlines 
    Chicago, IL (ORD)Belize City, BZ (BZE)07/15/201609:15 pm
    Belize City, BZ (BZE)Chicago, IL (ORD)07/29/201603:45 pm check price
  • $367American Airlines flight American Airlines 
    Chicago, IL (ORD)San Juan, PR (SJU)03/24/201706:35 pm
    San Juan, PR (SJU)Chicago, IL (ORD)04/02/201706:40 am check price
  • $376American Airlines flight American Airlines 
    Chicago, IL (ORD)St. Thomas Island, VI (STT)07/26/201605:30 am
    St. Thomas Island, VI (STT)Chicago, IL (ORD)08/08/201603:45 pm check price
  • $401Spirit Airlines flight Spirit Airlines 
    Chicago, IL (ORD)Montego Bay, JM (MBJ)08/08/201607:25 am
    Montego Bay, JM (MBJ)Chicago, IL (ORD)08/12/201602:58 pm check price
cheap domestic and international flights

Recently found cheap flight deals

Delta AirlinesLincoln To Dallas Delta Airlines airfares from Lincoln in June
$509 Depart: 06/09/2016
Return: 06/22/2016

provided by FlyFar

Multiple AirlinesLas Vegas To Veracruz Multiple Airlines airfares from Las Vegas in July
$725 Depart: 07/11/2016
Return: 07/25/2016

provided by

American AirlinesNew York City To Freeport American Airlines airfares from New York City in September
$597 Depart: 09/13/2016
Return: 09/21/2016

provided by FareDepot

Jetblue AirwaysNashville To Boston Jetblue Airways airfares from Nashville in June
$302 Depart: 06/27/2016
Return: 07/07/2016

provided by FareDepot

Multiple AirlinesSan Francisco To Bucharest Multiple Airlines airfares from San Francisco in June
$1507 Depart: 06/07/2016
Return: 06/21/2016

provided by FareDepot

American AirlinesChicago To Sarasota American Airlines airfares from Chicago in June
$536 Depart: 06/17/2016
Return: 06/22/2016

provided by FareDepot

Air CanadaEdmonton To Vancouver Air Canada airfares from Edmonton in October
$288 Depart: 10/08/2016
Return: 10/15/2016

provided by Travelgrove

Hawaiian AirlinesKona To Los Angeles Hawaiian Airlines airfares from Kona in November
$927 Depart: 11/26/2016
Return: 12/03/2016

provided by FlightHub

Major US CarrierBoston To Montego Bay Major US Carrier airfares from Boston in June
$573 Depart: 06/25/2016
Return: 07/04/2016

provided by FareDepot


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

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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