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.

Search and Compare cheap Flights

Enter your travel details:Step 1









Select merchants to compare:Step 2
FlightnetworkExpediaBookingbuddyCheapoairDealBaseTravelgroveTravelocityFareDepot
 
From $247 / RT details

Book your flight now with FlightHub and save!

Cheap San Juan airfares from $247/RT are provided by FlightHub. Outbound flight is leaving on 01/24/2017, 07:12 am from Chicago O`hare (ORD) airport and arrives at San Juan Marin Intl (SJU) at 01:18 am. The flight time is 18 hours and 6 minutes. The Returning flight departes on 02/05/2017, 02:05 am (other return dates are also available). Date posted: 04 Jan 2017

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

  • $247Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)01/24/201707:12 am
    San Juan, PR (SJU)Chicago, IL (ORD)02/05/201702:05 am
    flighthub.com check price
  • $258Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)01/24/201707:12 am
    San Juan, PR (SJU)Chicago, IL (ORD)02/05/201706:11 am
    flighthub.com check price
  • $262Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)02/22/201707:00 am
    San Juan, PR (SJU)Chicago, IL (ORD)02/28/201710:19 pm
    flighthub.com check price
  • $265Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)St. Thomas Island, VI (STT)02/05/201705:15 am
    St. Thomas Island, VI (STT)Chicago, IL (ORD)02/08/201705:17 pm
    flyfar.ca check price
  • $275Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)02/01/201707:12 am
    San Juan, PR (SJU)Chicago, IL (ORD)02/08/201706:06 am
    flighthub.com check price
  • $99Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Providenciales, TC (PLS)02/22/201707:00 am
    flighthub.com check price
  • $103Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Providenciales, TC (PLS)02/07/201707:12 am
    flighthub.com check price
  • $111Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Providenciales, TC (PLS)02/22/201707:00 am
    cheapoair.com check price
  • $111Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)02/08/201707:12 am
    flighthub.com check price
  • $115Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)01/25/201707:12 am
    flighthub.com check price
cheap domestic and international flights

Recently found cheap flight deals

American AirlinesSan Francisco To Memphis American Airlines airfares from San Francisco in February
$430 Depart: 02/07/2017
Return: 02/21/2017

provided by FareDepot

United AirlinesJacksonville To Dallas United Airlines airfares from Jacksonville in May
$372 Depart: 05/03/2017
Return: 05/09/2017

provided by FareDepot

Multiple AirlinesNew York City To Biloxi Multiple Airlines airfares from New York City in March
$405 Depart: 03/22/2017
Return: 04/04/2017

provided by FareDepot

United AirlinesLos Angeles To Vancouver United Airlines airfares from Los Angeles in April
$375 Depart: 04/26/2017
Return: 05/10/2017

provided by FareDepot

Multiple AirlinesLansing To Washington DC Multiple Airlines airfares from Lansing in February
$153 Depart: 02/04/2017
Return: 02/12/2017

provided by FareDepot

Avianca AirlinesLos Angeles To Cali Avianca Airlines airfares from Los Angeles in January
$533 Depart: 01/21/2017
Return: 01/31/2017

provided by FlightHub

Southwest AirlinesBaltimore To West Palm Beach Southwest Airlines airfares from Baltimore in February
$421 Depart: 02/23/2017
Return: 02/27/2017

provided by Flightnetwork

Multiple AirlinesToronto To Los Angeles Multiple Airlines airfares from Toronto in March
$500 Depart: 03/08/2017
Return: 03/15/2017

provided by FlightHub

Multiple AirlinesNew Orleans To Columbus Multiple Airlines airfares from New Orleans in May
$474 Depart: 05/26/2017
Return: 05/29/2017

provided by FareDepot

 

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

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!
*