Cheap flights from Chicago to Puerto Rico
Travel > Caribbean > Puerto Rico
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 Puerto Rico. 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 Puerto Rico, you will need to run a search below.
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Cheap Aguadilla airfares from $178/RT are provided by Cheapoair.com. Outbound flight is leaving on 01/26/2025, 10:58 am from Chicago Midway (MDW) airport and arrives at Aguadilla Borinquen (BQN) at 02:46 am. The flight time is 15 hours and 48 minutes. The Returning flight departes on 02/09/2025, 03:51 am (other return dates are also available). Date posted: 27 Nov 2024
Price evolution for flights From Chicago To Puerto Rico
Recent Deals on Flights from Chicago to Puerto Rico:Roundtrip / Oneway
- $178
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) Aguadilla, PR (BQN) 01/26/2025 10:58 am Aguadilla, PR (BQN) Chicago, IL (MDW) 02/09/2025 03:51 am - $253
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 01/03/2025 01:00 pm San Juan, PR (SJU) Chicago, IL (ORD) 01/12/2025 10:09 pm - $256 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 03/08/2025 07:00 am San Juan, PR (SJU) Chicago, IL (ORD) 03/16/2025 03:35 pm - $260 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 01/03/2025 06:40 am San Juan, PR (SJU) Chicago, IL (ORD) 01/12/2025 09:49 pm - $516
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 03/08/2025 02:06 pm San Juan, PR (SJU) Chicago, IL (ORD) 03/16/2025 03:35 pm - $89 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Aguadilla, PR (BQN) 01/24/2025 10:59 am - $199 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) San Juan, PR (SJU) 12/25/2024 06:50 am - $243 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 12/25/2024 03:31 pm - $257 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Aguadilla, PR (BQN) 12/23/2024 10:59 am - $260 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Ponce, PR (PSE) 12/29/2024 07:29 pm
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Know what to do when flying to Puerto Rico?
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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