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 CondadoCheck 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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Cheap San Juan airfares from $227/RT are provided by Cheapoair.com. Outbound flight is leaving on 12/04/2021, 05:21 pm from Chicago O`hare (ORD) airport and arrives at San Juan Marin Intl (SJU) at 09:18 am. The flight time is 15 hours and 57 minutes. The Returning flight departes on 12/19/2021, 01:00 pm (other return dates are also available). Date posted: 07 Nov 2021
Price evolution for flights From Chicago To Caribbean
Recent Deals on Flights from Chicago to Caribbean:Roundtrip / Oneway
- $227
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 12/04/2021 05:21 pm San Juan, PR (SJU) Chicago, IL (ORD) 12/19/2021 01:00 pm - $278 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Port Au Prince, HT (PAP) 02/02/2022 06:15 am Port Au Prince, HT (PAP) Chicago, IL (ORD) 02/16/2022 09:51 am - $303 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Montego Bay, JM (MBJ) 12/08/2021 05:25 am Montego Bay, JM (MBJ) Chicago, IL (ORD) 12/13/2021 01:50 pm - $322 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Santiago, DO (STI) 02/08/2022 05:43 pm Santiago, DO (STI) Chicago, IL (ORD) 02/15/2022 03:55 am - $452
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Santiago, DO (STI) 02/08/2022 07:53 am Santiago, DO (STI) Chicago, IL (ORD) 02/15/2022 03:55 am - $66 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Port Au Prince, HT (PAP) 12/11/2021 05:43 pm - $269 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Port Au Prince, HT (PAP) 12/22/2021 06:15 am - $279
Air Canada
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Fort De France, MQ (FDF) 02/01/2022 01:55 pm - $324 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Santiago, DO (STI) 12/21/2021 05:43 pm - $339
Westjet
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Hamilton, BM (BDA) 12/08/2021 10:30 am
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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 [...]
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