Cheap flights from Illinois to Caribbean

Travel > Caribbean

Basically, Montego Bay remained a small town till the first half of the 18th century. Taxes were exempted here till 1788. It was a little after 1720 that a captain named Jonathan Barnett had divided a part of his sugar cane fields to create Charles Town, Barnett Town and Charles or the Sam Sharpe Square of today. With this diversification of land in Montego Bay, the town started expanding rapidly.... (read more in our Montego Bay History)

Check current prices for flights to Caribbean at our partners' sites:

Search and Compare cheap Flights

Enter your travel details:Step 1

Select merchants to compare:Step 2

Cheapest flights found for the next 6 months

(click city name to see more / use right arrow to view later months)

Check our newest flight offers to Caribbean:

  • $326Spirit Airlines flight Spirit Airlines 
    Chicago, IL (ORD)Aguadilla, PR (BQN)11/14/201706:19 pm
    Aguadilla, PR (BQN)Chicago, IL (ORD)11/21/201704:21 am check price
  • $336Frontier Airlines flight Frontier Airlines 
    Chicago, IL (ORD)San Juan, PR (SJU)11/14/201707:30 am
    San Juan, PR (SJU)Chicago, IL (ORD)11/21/201703:05 am check price
  • $422Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)V.C. Bird International, AG (ANU)09/25/201708:44 pm
    V.C. Bird International, AG (ANU)Chicago, IL (ORD)10/03/201702:24 pm check price
  • $423Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)Kingston, JM (KIN)09/28/201706:45 am
    Kingston, JM (KIN)Chicago, IL (ORD)10/03/201707:57 am check price
  • $456Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)Montego Bay, JM (MBJ)09/28/201706:45 am
    Montego Bay, JM (MBJ)Chicago, IL (ORD)10/03/201707:57 am check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesAtlanta To Grand Rapids Multiple Airlines airfares from Atlanta in September
$563 Depart: 09/11/2017
Return: 09/25/2017

provided by Flightnetwork

United AirlinesBaton Rouge To Atlanta United Airlines airfares from Baton Rouge in September
$273 Depart: 09/11/2017
Return: 09/19/2017

provided by FlyFar

Jetblue AirwaysSan Jose To Baltimore Jetblue Airways airfares from San Jose in December
$554 Depart: 12/13/2017
Return: 12/19/2017

provided by

United AirlinesOrange County To New Orleans United Airlines airfares from Orange County in September
$425 Depart: 09/15/2017
Return: 09/18/2017

provided by FlightHub

United AirlinesRichmond To Newark United Airlines airfares from Richmond in September
$313 Depart: 09/02/2017
Return: 09/16/2017

provided by FlightHub

United AirlinesHouston To Mcallen United Airlines airfares from Houston in October
$308 Depart: 10/11/2017
Return: 10/25/2017

provided by FlightHub

Jetblue AirwaysCleveland To Durham Jetblue Airways airfares from Cleveland in August
$470 Depart: 08/21/2017
Return: 08/28/2017

provided by

United AirlinesPittsburgh To Minneapolis United Airlines airfares from Pittsburgh in January
$374 Depart: 01/02/2018
Return: 01/16/2018

provided by FlyFar

United AirlinesNewark To Madison United Airlines airfares from Newark in November
$255 Depart: 11/07/2017
Return: 11/14/2017

provided by FlyFar


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

more Caribbean travel deals

   Welcome to Travelgrove  register tell a friend bookmark it 
This airfare deal was found   ago. Click "Check price" to see current prices!