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.
Search and Compare cheap Flights
Book your flight now with Cheapoair.com and save!
Cheap San Juan airfares from $199/RT are provided by Cheapoair.com. Outbound flight is leaving on 04/03/2024, 11:20 am from Chicago O`hare (ORD) airport and arrives at San Juan Marin Intl (SJU) at 04:59 pm. The flight time is 5 hours and 39 minutes. The Returning flight departes on 04/10/2024, 02:11 pm (other return dates are also available). Date posted: 29 Jan 2024
Price evolution for flights From Chicago To Puerto Rico
Recent Deals on Flights from Chicago to Puerto Rico:Roundtrip / Oneway
- $199 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 04/03/2024 11:20 am San Juan, PR (SJU) Chicago, IL (ORD) 04/10/2024 02:11 pm - $213 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Aguadilla, PR (BQN) 04/20/2024 08:25 am Aguadilla, PR (BQN) Chicago, IL (ORD) 04/26/2024 02:45 am - $213 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) Aguadilla, PR (BQN) 03/29/2024 07:55 am Aguadilla, PR (BQN) Chicago, IL (MDW) 04/12/2024 02:45 am - $229 Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 04/03/2024 11:20 am San Juan, PR (SJU) Chicago, IL (ORD) 04/10/2024 03:00 pm - $244 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) Aguadilla, PR (BQN) 04/02/2024 03:11 pm Aguadilla, PR (BQN) Chicago, IL (MDW) 04/08/2024 02:40 am - $89 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 04/17/2024 11:20 am - $93 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 04/04/2024 05:59 pm - $122 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) San Juan, PR (SJU) 04/17/2024 12:28 pm - $122 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 04/04/2024 06:21 pm - $140 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) Aguadilla, PR (BQN) 04/03/2024 07:55 am
Recently found cheap flight deals
Boston To New Orleans Spirit Airlines airfares from Boston in April
$248 Depart: 04/14/2024
Return: 04/25/2024
provided by Cheapoair.com
Dallas To Bologna Multiple Airlines airfares from Dallas in August
$1077 Depart: 08/18/2020
Return: 08/25/2020
provided by FlyFar
Philadelphia To Portland Multiple Airlines airfares from Philadelphia in March
$349 Depart: 03/09/2024
Return: 03/17/2024
provided by Cheapoair.com
Los Angeles To Cozumel Multiple Airlines airfares from Los Angeles in March
$672 Depart: 03/27/2024
Return: 04/16/2024
provided by Cheapoair.com
Chicago To San Pedro Sula Aeromexico airfares from Chicago in March
$862 Depart: 03/26/2024
Return: 04/02/2024
provided by Cheapoair.com
Fayetteville To Houston Frontier Airlines airfares from Fayetteville in March
$278 Depart: 03/30/2024
Return: 04/12/2024
provided by Cheapoair.com
Houston To Lisbon Lufthansa airfares from Houston in April
$1026 Depart: 04/10/2024
Return: 04/16/2024
provided by Cheapoair.com
Las Vegas To Billings Alaska Airlines airfares from Las Vegas in February
$910 Depart: 02/08/2024
Return: 02/16/2024
provided by Cheapoair.com
Houston To Vienna British Airways airfares from Houston in April
$1106 Depart: 04/17/2024
Return: 04/30/2024
provided by Cheapoair.com
Specify your search details. Browse the cheapest flights from Chicago to Puerto Rico, Puerto Rico hotel rooms and Chicago to Puerto Rico vacation packages from the most popular providers, airline consolidators and travel search engines.
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 [...]