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 $253/RT are provided by Cheapoair.com. Outbound flight is leaving on 01/03/2025, 01:00 pm from Chicago O`hare (ORD) airport and arrives at San Juan Marin Intl (SJU) at 07:36 pm. The flight time is 6 hours and 36 minutes. The Returning flight departes on 01/12/2025, 10:09 pm (other return dates are also available). Date posted: 13 Nov 2024
Price evolution for flights From Chicago To Puerto Rico
Recent Deals on Flights from Chicago to Puerto Rico:Roundtrip / Oneway
- $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 - $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 - $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 - $199 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) San Juan, PR (SJU) 12/25/2024 06:50 am - $215 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Aguadilla, PR (BQN) 12/15/2024 09:35 am - $243 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 12/25/2024 03:31 pm
Recently found cheap flight deals
Oakland To Oslo Multiple Airlines airfares from Oakland in January
$1802 Depart: 01/20/2023
Return: 01/28/2023
provided by Cheapoair.com
San Francisco To Amritsar Multiple Airlines airfares from San Francisco in August
$1032 Depart: 08/27/2024
Return: 09/07/2024
provided by Cheapoair.com
Portland To Charlotte Frontier Airlines airfares from Portland in February
$167 Depart: 02/21/2023
Return: 03/07/2023
provided by Cheapoair.com
Houston To Sarasota Jetblue Airways airfares from Houston in December
$627 Depart: 12/23/2020
Return: 12/29/2020
provided by Cheapoair.com
Minneapolis To Manila Multiple Airlines airfares from Minneapolis in November
$3115 Depart: 11/24/2021
Return: 12/05/2021
provided by Cheapoair.com
Los Angeles To Riga LOT Polish Airlines airfares from Los Angeles in April
$937 Depart: 04/24/2023
Return: 05/03/2023
provided by Cheapoair.com
Chicago To Pensacola Multiple Airlines airfares from Chicago in March
$997 Depart: 03/11/2025
Return: 03/26/2025
provided by Cheapoair.com
San Jose To Santo Domingo Multiple Airlines airfares from San Jose in December
$1302 Depart: 12/08/2024
Return: 12/13/2024
provided by Cheapoair.com
New York City To Dubrovnik Multiple Airlines airfares from New York City in August
$1644 Depart: 08/31/2024
Return: 09/12/2024
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 [...]
© Copyright 2004 - 2024 Travelgrove, Inc.