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
BookingbuddyDealBaseTravelocityPricelineTripAdvisorTravelgrove
 
From $351 / RT details

Book your flight now with Cheapoair.com and save!

Cheap St. Thomas Island airfares from $351/RT are provided by Cheapoair.com. Outbound flight is leaving on 07/31/2013, 05:30 am from Chicago O`hare (ORD) airport and arrives at St Thomas Island Cyril King (STT) at 03:31 pm. The flight time is 10 hours and 1 minutes. The Returning flight departes on 08/05/2013, 04:13 pm (other return dates are also available). Date posted: 01 Oct 2012

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

  • $351Major Airline flight Major Airline 
    FromToDepartureTime
    Chicago, IL (ORD)St. Thomas Island, VI (STT)07/31/201305:30 am
    St. Thomas Island, VI (STT)Chicago, IL (ORD)08/05/201304:13 pm
    cheapoair.com check price
  • $372Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Nassau, BS (NAS)07/11/201305:30 am
    Nassau, BS (NAS)Chicago, IL (MDW)07/17/201305:22 pm
    cheapoair.com check price
  • $384Delta Airlines flight Delta Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Nassau, BS (NAS)07/11/201309:59 am
    Nassau, BS (NAS)Chicago, IL (MDW)07/17/201308:50 am
    flighthub.com check price
  • $387United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/11/201309:35 pm
    Nassau, BS (NAS)Chicago, IL (ORD)07/17/201301:00 pm
    flighthub.com check price
  • $390Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Nassau, BS (NAS)07/11/201305:30 am
    Nassau, BS (NAS)Chicago, IL (MDW)07/17/201305:22 pm
    faredepot.com check price
  • $400Delta Airlines flight Delta Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/11/201310:15 am
    Nassau, BS (NAS)Chicago, IL (ORD)07/17/201308:50 am
    flighthub.com check price
  • $402Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)08/01/201307:10 am
    Hamilton, BM (BDA)Chicago, IL (MDW)08/16/201303:09 pm
    expedia.com check price
  • $402Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)07/24/201307:10 am
    Hamilton, BM (BDA)Chicago, IL (MDW)08/06/201303:09 pm
    expedia.com check price
  • $409Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)08/01/201306:52 pm
    Hamilton, BM (BDA)Chicago, IL (MDW)08/16/201303:09 pm
    cheapoair.com check price
  • $409Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)07/24/201305:40 am
    Hamilton, BM (BDA)Chicago, IL (MDW)08/06/201303:09 pm
    faregeek.com check price
  • $409Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)08/01/201305:40 am
    Hamilton, BM (BDA)Chicago, IL (MDW)08/16/201303:09 pm
    faregeek.com check price
  • $416Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)07/25/201308:52 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/08/201303:00 am
    cheapoair.com check price
  • $425Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)07/25/201308:52 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/08/201303:00 am
    flighthub.com check price
  • $425Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)07/25/201308:52 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/08/201303:00 am
    faregeek.com check price
  • $427United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)10/12/201304:00 pm
    Nassau, BS (NAS)Chicago, IL (ORD)10/19/201301:15 pm
    flighthub.com check price
  • $428United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/11/201309:35 pm
    Nassau, BS (NAS)Chicago, IL (ORD)07/17/201303:17 pm
    faredepot.com check price
  • $435United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)07/24/201309:35 pm
    Hamilton, BM (BDA)Chicago, IL (ORD)08/06/201303:45 pm
    faregeek.com check price
  • $445American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/11/201305:30 am
    Nassau, BS (NAS)Chicago, IL (ORD)07/17/201303:50 pm
    faredepot.com check price
  • $447Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)08/01/201307:45 am
    Hamilton, BM (BDA)Chicago, IL (ORD)08/16/201303:35 pm
    flighthub.com check price
  • $449United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)08/01/201305:00 am
    Hamilton, BM (BDA)Chicago, IL (ORD)08/16/201303:45 pm
    flighthub.com check price
  • $449American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)10/12/201307:25 pm
    Nassau, BS (NAS)Chicago, IL (ORD)10/19/201305:05 pm
    travelgrove.com check price
  • $450United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)07/24/201302:00 pm
    Hamilton, BM (BDA)Chicago, IL (ORD)08/06/201303:45 pm
    flighthub.com check price
  • $450Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)07/24/201306:00 am
    Hamilton, BM (BDA)Chicago, IL (ORD)08/06/201303:35 pm
    flighthub.com check price
  • $452United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)12/14/201305:00 am
    Nassau, BS (NAS)Chicago, IL (ORD)12/28/201301:50 pm
    faregeek.com check price
  • $453American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)10/12/201307:00 am
    Nassau, BS (NAS)Chicago, IL (ORD)10/19/201305:05 pm
    faregeek.com check price
  • $456Delta Airlines flight Delta Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)07/24/201304:50 pm
    Hamilton, BM (BDA)Chicago, IL (MDW)08/06/201303:54 pm
    flighthub.com check price
  • $457United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)08/01/201309:35 pm
    Hamilton, BM (BDA)Chicago, IL (ORD)08/16/201303:45 pm
    faredepot.com check price
  • $461United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)07/24/201309:35 pm
    Hamilton, BM (BDA)Chicago, IL (ORD)08/06/201303:45 pm
    faredepot.com check price
  • $461United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)09/12/201302:00 pm
    Aguadilla, PR (BQN)Chicago, IL (ORD)09/21/201301:55 am
    flighthub.com check price
  • $462Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aruba, AW (AUA)06/29/201305:30 am
    Aruba, AW (AUA)Chicago, IL (ORD)07/06/201303:05 pm
    cheapoair.com check price
  • $147Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Nassau, BS (NAS)07/04/201310:20 am
    cheapoair.com check price
  • $157Delta Airlines flight Delta Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Nassau, BS (NAS)07/04/201306:00 am
    flighthub.com check price
  • $158United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/04/201301:05 pm
    flighthub.com check price
  • $160American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/04/201306:00 am
    faregeek.com check price
  • $164Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/04/201305:45 am
    faregeek.com check price
  • $165Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Nassau, BS (NAS)07/04/201310:20 am
    faredepot.com check price
  • $174Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)07/11/201307:10 am
    expedia.com check price
  • $178American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/04/201306:00 am
    faredepot.com check price
  • $182United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/04/201307:15 pm
    faredepot.com check price
  • $184Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Hamilton, BM (BDA)07/11/201305:40 am
    faregeek.com check price
  • $184Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Montego Bay, JM (MBJ)08/08/201308:52 pm
    cheapoair.com check price
  • $186Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)San Juan, PR (SJU)08/06/201306:45 am
    cheapoair.com check price
  • $207Air Tran flight Air Tran 
    FromToDepartureTime
    Chicago, IL (MDW)Montego Bay, JM (MBJ)08/08/201308:52 pm
    faredepot.com check price
  • $215Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)07/04/201305:07 pm
    cheapoair.com check price
  • $220Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/06/201308:59 am
    cheapoair.com check price
  • $220Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)07/04/201305:07 pm
    expedia.com check price
  • $224Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/06/201308:59 am
    flighthub.com check price
  • $228Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)07/04/201306:50 am
    cheapoair.com check price
  • $233Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)07/04/201305:07 pm
    faredepot.com check price
  • $234Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Montego Bay, JM (MBJ)08/08/201307:30 am
    cheapoair.com check price
  • $239Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/06/201305:30 am
    cheapoair.com check price
  • $246Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)St. Thomas Island, VI (STT)08/14/201307:30 am
    cheapoair.com check price
  • $246Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Montego Bay, JM (MBJ)08/08/201307:30 am
    faredepot.com check price
  • $247Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Montego Bay, JM (MBJ)08/08/201309:04 pm
    flighthub.com check price
  • $247United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/06/201303:25 pm
    flighthub.com check price
  • $257Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)07/11/201307:45 am
    flighthub.com check price
  • $258United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)07/11/201307:00 am
    faregeek.com check price
  • $259United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)07/11/201303:25 pm
    flighthub.com check price
  • $261Delta Airlines flight Delta Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)San Juan, PR (SJU)08/06/201309:18 am
    flighthub.com check price
  • $261Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)07/19/201305:07 pm
    cheapoair.com check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesCheap Flights From Cleveland To Kuwait City Multiple Airlines airfares from Cleveland in July
$1556 Depart: 07/17/2013
Return: 07/23/2013
provided by Faregeek

American AirlinesCheap Flights From New York City To Santa Barbara American Airlines airfares from New York City in July
$675 Depart: 07/10/2013
Return: 07/18/2013
provided by FlightHub

Multiple AirlinesCheap Flights From Anaheim To Seattle Multiple Airlines airfares from Anaheim in October
$199 Depart: 10/11/2013
Return: 10/19/2013
provided by Cheapoair.com

United AirlinesCheap Flights From Las Vegas To Morelia United Airlines airfares from Las Vegas in July
$658 Depart: 07/05/2013
Return: 08/06/2013
provided by Faregeek

United AirlinesCheap Flights From Reno To Los Angeles United Airlines airfares from Reno in August
$209 Depart: 08/15/2013
Return: 08/29/2013
provided by Faregeek

Frontier AirlinesCheap Flights From Albuquerque To Indianapolis Frontier Airlines airfares from Albuquerque in July
$351 Depart: 07/18/2013
Return: 07/27/2013
provided by FlightHub

United AirlinesCheap Flights From Los Angeles To Binghamton United Airlines airfares from Los Angeles in August
$472 Depart: 08/20/2013
Return: 08/28/2013
provided by FareDepot

United AirlinesCheap Flights From Denver To Austin United Airlines airfares from Denver in September
$180 Depart: 09/24/2013
Return: 10/01/2013
provided by FlightHub

Multiple AirlinesCheap Flights From Orlando To Vancouver Multiple Airlines airfares from Orlando in July
$625 Depart: 07/01/2013
Return: 07/08/2013
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

more Caribbean travel deals

   Welcome to Travelgrove  register tell a friend bookmark it 
 

cheap flights | hotel rooms | car rentals | cruise search | cheap vacations | travel deals | community | travel guides | Travel Tips | forum | blog

popular flights | destination reviews | about us | advertising | partners | affiliates | FAQ | privacy | terms of service | travel insurance | frequent flyer

Travelgrove© Copyright 2004 - 2013 Travelgrove, Inc.
All rights reserved
Travelgrove Inc is not responsible for content on external Web sites.

Visit our international sites:
Other sites we like:Metafares.com
Travengo.com


Travelgrove news
what's happening on travelgroveQuestions about how to use Travelgrove
read our F.A.Q. for helpTell us your opinion
help travelgrove improve

This airfare deal was found   ago. Click "Check price" to see current prices!
*