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 CondadoCheck 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.
Search and Compare cheap Flights
Book your flight now with FlyFar and save!
Cheap San Juan airfares from $72/RT are provided by FlyFar. Outbound flight is leaving on 06/13/2020, 05:20 am from Chicago O`hare (ORD) airport and arrives at San Juan Marin Intl (SJU) at 01:16 pm. The flight time is 7 hours and 56 minutes. The Returning flight departes on 06/24/2020, 02:11 pm (other return dates are also available). Date posted: 14 Apr 2020
Price evolution for flights From Chicago To Caribbean
Recent Deals on Flights from Chicago to Caribbean:Roundtrip / Oneway
- $72
Spirit Airlines
flyfar.ca check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 06/13/2020 05:20 am San Juan, PR (SJU) Chicago, IL (ORD) 06/24/2020 02:11 pm - $127
Multiple Airlines
flyfar.ca check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 06/13/2020 05:20 am San Juan, PR (SJU) Chicago, IL (ORD) 06/24/2020 12:38 pm - $196 Spirit Airlines
travelgrove.com check priceFrom To Departure Time Chicago, IL (ORD) Santo Domingo, DO (SDQ) 06/02/2020 04:45 pm Santo Domingo, DO (SDQ) Chicago, IL (ORD) 06/09/2020 01:58 pm - $236
Frontier Airlines
flyfar.ca check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 07/10/2020 06:45 am San Juan, PR (SJU) Chicago, IL (ORD) 07/24/2020 01:40 pm - $243 Multiple Airlines
flyfar.ca check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 07/10/2020 02:13 pm San Juan, PR (SJU) Chicago, IL (ORD) 07/24/2020 01:40 pm - $89
Jetblue Airways
flyfar.ca check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 06/13/2020 05:09 am - $104 Jetblue Airways
flyfar.ca check priceFrom To Departure Time Chicago, IL (ORD) Grand Cayman, KY (GCM) 06/13/2020 05:09 am - $107 Spirit Airlines
flyfar.ca check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 07/22/2020 06:28 pm - $118 Jetblue Airways
flyfar.ca check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 06/15/2020 05:09 am - $122 Jetblue Airways
flyfar.ca check priceFrom To Departure Time Chicago, IL (ORD) Nassau, BS (NAS) 06/13/2020 05:09 am
Recently found cheap flight deals
San Francisco To Natal Multiple Airlines airfares from San Francisco in July
$1496 Depart: 07/07/2020
Return: 07/15/2020
provided by Travelgrove
Washington DC To Windhoek Multiple Airlines airfares from Washington DC in September
$1436 Depart: 09/09/2020
Return: 09/15/2020
provided by FlyFar
San Francisco To San Jose Jetblue Airways airfares from San Francisco in June
$576 Depart: 06/09/2020
Return: 06/23/2020
provided by Travelgrove
Baltimore To La Paz Multiple Airlines airfares from Baltimore in July
$1679 Depart: 07/02/2020
Return: 07/13/2020
provided by FlyFar
Atlanta To Florence Multiple Airlines airfares from Atlanta in October
$1794 Depart: 10/13/2019
Return: 10/20/2019
provided by Cheapoair.com
New York City To Lagos Multiple Airlines airfares from New York City in August
$1410 Depart: 08/12/2020
Return: 08/19/2020
provided by Travelgrove
Vancouver To San Francisco Multiple Airlines airfares from Vancouver in June
$251 Depart: 06/29/2020
Return: 07/12/2020
provided by FlyFar
Las Vegas To Manila Singapore Airlines airfares from Las Vegas in June
$923 Depart: 06/30/2020
Return: 07/07/2020
provided by FlyFar
San Francisco To Da Nang Multiple Airlines airfares from San Francisco in December
$1414 Depart: 12/18/2018
Return: 01/22/2019
provided by Flightnetwork
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 [...]
© Copyright 2004 - 2020 Travelgrove, Inc.