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 Aguadilla airfares from $249/RT are provided by Cheapoair.com. Outbound flight is leaving on 04/11/2023, 05:30 pm from Chicago O`hare (ORD) airport and arrives at Aguadilla Borinquen (BQN) at 01:08 am. The flight time is 7 hours and 38 minutes. The Returning flight departes on 04/25/2023, 04:24 am (other return dates are also available). Date posted: 26 Jan 2023
Price evolution for flights From Chicago To Caribbean

Recent Deals on Flights from Chicago to Caribbean:Roundtrip / Oneway
- $249
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Aguadilla, PR (BQN) 04/11/2023 05:30 pm Aguadilla, PR (BQN) Chicago, IL (ORD) 04/25/2023 04:24 am - $251
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Aguadilla, PR (BQN) 02/15/2023 05:30 pm Aguadilla, PR (BQN) Chicago, IL (ORD) 02/25/2023 02:59 am - $275
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Santo Domingo, DO (SDQ) 02/26/2023 06:24 pm Santo Domingo, DO (SDQ) Chicago, IL (ORD) 03/03/2023 08:00 am - $275
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Aguadilla, PR (BQN) 03/13/2023 04:55 pm Aguadilla, PR (BQN) Chicago, IL (ORD) 03/22/2023 01:59 am - $278
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Santo Domingo, DO (SDQ) 02/26/2023 08:00 pm Santo Domingo, DO (SDQ) Chicago, IL (ORD) 03/03/2023 08:00 am - $89
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Aguadilla, PR (BQN) 02/28/2023 09:10 am - $90
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) Aguadilla, PR (BQN) 03/06/2023 07:15 am - $90
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) Aguadilla, PR (BQN) 02/28/2023 07:15 am - $110
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) San Juan, PR (SJU) 02/26/2023 03:05 pm - $126
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 02/26/2023 05:30 pm
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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 [...]