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 $220 / RT details

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Cheap Aguadilla airfares from $220/RT are provided by Cheapoair.com. Outbound flight is leaving on 10/22/2022, 05:30 pm from Chicago O`hare (ORD) airport and arrives at Aguadilla Borinquen (BQN) at 01:59 am. The flight time is 8 hours and 29 minutes. The Returning flight departes on 10/31/2022, 09:45 pm (other return dates are also available). Date posted: 23 Sep 2022

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

  • $220Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)10/22/202205:30 pm
    Aguadilla, PR (BQN)Chicago, IL (ORD)10/31/202209:45 pm
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  • $249Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)10/25/202210:38 am
    Aguadilla, PR (BQN)Chicago, IL (ORD)11/02/202201:56 am
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  • $255Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)10/19/202205:30 pm
    Aguadilla, PR (BQN)Chicago, IL (ORD)11/02/202202:59 am
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  • $269Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Santo Domingo, DO (SDQ)11/06/202203:16 pm
    Santo Domingo, DO (SDQ)Chicago, IL (MDW)11/11/202209:38 pm
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  • $287Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)10/15/202205:30 pm
    San Juan, PR (SJU)Chicago, IL (ORD)10/20/202209:19 am
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  • $92Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)10/18/202208:53 am
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  • $107Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)10/11/202205:30 pm
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  • $129Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Montego Bay, JM (MBJ)10/15/202206:23 pm
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  • $130Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)11/24/202206:20 pm
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  • $134Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)10/06/202205:30 pm
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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 [...]
San Juan Pictures
  • El Morro - San Juanview
  • San Juan, Puerto Rico - San Juanview
  • San Juan, Puerto Rico - San Juanview
  • El Morro - San Juanview
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