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 $323 / RT details

Book your flight now with FlightHub and save!

Cheap San Juan airfares from $323/RT are provided by FlightHub. Outbound flight is leaving on 08/30/2016, 07:30 am from Chicago O`hare (ORD) airport and arrives at San Juan Marin Intl (SJU) at 01:10 pm. The flight time is 5 hours and 40 minutes. The Returning flight departes on 09/14/2016, 02:20 pm (other return dates are also available). Date posted: 02 Apr 2016

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

  • $323United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/30/201607:30 am
    San Juan, PR (SJU)Chicago, IL (ORD)09/14/201602:20 pm
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  • $323Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/30/201611:55 am
    San Juan, PR (SJU)Chicago, IL (ORD)09/14/201602:20 pm
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  • $327Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/30/201607:30 am
    San Juan, PR (SJU)Chicago, IL (ORD)09/06/201602:14 pm
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  • $333Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)09/14/201605:15 am
    San Juan, PR (SJU)Chicago, IL (ORD)09/20/201604:15 pm
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  • $333Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)10/05/201605:15 am
    San Juan, PR (SJU)Chicago, IL (ORD)10/19/201604:15 pm
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  • $155American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Belize City, BZ (BZE)09/19/201604:33 pm
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  • $155United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Belize City, BZ (BZE)09/19/201607:30 pm
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  • $166American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Punta Cana, DO (PUJ)07/07/201606:45 pm
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  • $167American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Punta Cana, DO (PUJ)07/07/201606:45 pm
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  • $172United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/10/201607:30 am
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Recently found cheap flight deals

Jetblue AirwaysOakland To Chicago Jetblue Airways airfares from Oakland in June
$854 Depart: 06/29/2016
Return: 07/06/2016

provided by FlightHub

United AirlinesBaltimore To Santo Domingo United Airlines airfares from Baltimore in July
$931 Depart: 07/28/2016
Return: 08/14/2016

provided by FlightHub

Southwest AirlinesNew York City To Pittsburgh Southwest Airlines airfares from New York City in June
$449 Depart: 06/30/2016
Return: 07/03/2016

provided by Flightnetwork

Emirates AirlinesOrlando To Manama Emirates Airlines airfares from Orlando in August
$1591 Depart: 08/10/2016
Return: 08/17/2016

provided by FlightHub

American AirlinesNewark To Tucson American Airlines airfares from Newark in June
$595 Depart: 06/19/2016
Return: 06/26/2016

provided by FlyFar

Multiple AirlinesChicago To Las Vegas Multiple Airlines airfares from Chicago in July
$403 Depart: 07/21/2016
Return: 07/24/2016

provided by Flightnetwork

United AirlinesAustin To Palm Springs United Airlines airfares from Austin in July
$611 Depart: 07/04/2016
Return: 07/17/2016

provided by FareDepot

Multiple AirlinesAtlanta To Acapulco Multiple Airlines airfares from Atlanta in July
$1040 Depart: 07/10/2016
Return: 07/22/2016

provided by FlightHub

Air CanadaNew York City To Algiers Air Canada airfares from New York City in July
$2032 Depart: 07/14/2016
Return: 08/13/2016

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

more Caribbean travel deals

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