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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Book your flight now with Cheapoair.com and save!
Cheap San Juan airfares from $256/RT are provided by Cheapoair.com. Outbound flight is leaving on 03/08/2025, 07:00 am from Chicago O`hare (ORD) airport and arrives at San Juan Marin Intl (SJU) at 03:45 pm. The flight time is 8 hours and 45 minutes. The Returning flight departes on 03/16/2025, 03:35 pm (other return dates are also available). Date posted: 29 Aug 2024
Price evolution for flights From Chicago To Puerto Rico
Recent Deals on Flights from Chicago to Puerto Rico:Roundtrip / Oneway
- $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 - $288
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Ponce, PR (PSE) 11/06/2024 05:56 pm Ponce, PR (PSE) Chicago, IL (ORD) 11/19/2024 01:09 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 - $528 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 11/23/2024 05:41 pm San Juan, PR (SJU) Chicago, IL (ORD) 11/27/2024 09:59 pm - $530 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Aguadilla, PR (BQN) 11/25/2024 08:21 pm Aguadilla, PR (BQN) Chicago, IL (ORD) 12/02/2024 11:55 am - $85 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 12/10/2024 01:00 pm - $89 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) Aguadilla, PR (BQN) 12/09/2024 11:33 am - $100 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 11/21/2024 03:34 pm - $126 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 11/20/2024 05:00 am - $139 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) San Juan, PR (SJU) 11/21/2024 06:48 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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