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 Condado

Check 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

Enter your travel details:Step 1









Select merchants to compare:Step 2
Travelgrove
 
From $316 / RT details

Book your flight now with Cheapoair.com and save!

Cheap San Juan airfares from $316/RT are provided by Cheapoair.com. Outbound flight is leaving on 05/31/2022, 05:30 pm from Chicago O`hare (ORD) airport and arrives at San Juan Marin Intl (SJU) at 01:14 am. The flight time is 7 hours and 44 minutes. The Returning flight departes on 06/09/2022, 06:30 am (other return dates are also available). Date posted: 10 Apr 2022

Price evolution for flights From Chicago To Caribbean

Price overview for flights from Chicago to Caribbean

Recent Deals on Flights from Chicago to Caribbean:Roundtrip / Oneway

  • $316Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)05/31/202205:30 pm
    San Juan, PR (SJU)Chicago, IL (ORD)06/09/202206:30 am
    cheapoair.com check price
  • $328Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)05/31/202208:00 am
    San Juan, PR (SJU)Chicago, IL (ORD)06/09/202204:55 pm
    cheapoair.com check price
  • $348Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)07/27/202212:25 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/09/202206:30 am
    cheapoair.com check price
  • $357Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)07/27/202212:25 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/09/202212:00 pm
    cheapoair.com check price
  • $370Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Santiago, DO (STI)05/29/202208:00 am
    Santiago, DO (STI)Chicago, IL (ORD)06/03/202202:47 am
    cheapoair.com check price
  • $75Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)05/20/202205:40 pm
    cheapoair.com check price
  • $82Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Nassau, BS (NAS)06/01/202211:24 am
    cheapoair.com check price
  • $141Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)06/07/202205:30 pm
    cheapoair.com check price
  • $145Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/31/202205:00 am
    cheapoair.com check price
  • $152Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)05/18/202207:00 am
    cheapoair.com check price
cheap domestic and international flights

Recently found cheap flight deals

Major CarrierSeattle To Manchester Major Carrier airfares from Seattle in September
$538 Depart: 09/14/2019
Return: 09/20/2019

provided by FlyFar

Multiple AirlinesFort Lauderdale To San Jose Multiple Airlines airfares from Fort Lauderdale in May
$285 Depart: 05/28/2022
Return: 06/06/2022

provided by Cheapoair.com

Multiple AirlinesNew York City To Cairns Multiple Airlines airfares from New York City in June
$2267 Depart: 06/15/2022
Return: 06/27/2022

provided by Cheapoair.com

Thy Turkish AirlinesWashington DC To Hong Kong Thy Turkish Airlines airfares from Washington DC in June
$1148 Depart: 06/29/2022
Return: 07/05/2022

provided by Cheapoair.com

Multiple AirlinesHouston To Tunis Multiple Airlines airfares from Houston in June
$1713 Depart: 06/23/2020
Return: 07/01/2020

provided by FlyFar

Alaska AirlinesMilwaukee To New York City Alaska Airlines airfares from Milwaukee in August
$1024 Depart: 08/24/2021
Return: 09/04/2021

provided by Cheapoair.com

Multiple AirlinesToronto To Long Beach Multiple Airlines airfares from Toronto in May
$1038 Depart: 05/26/2022
Return: 06/02/2022

provided by Cheapoair.com

Multiple AirlinesBaltimore To Saint Thomas Multiple Airlines airfares from Baltimore in June
$602 Depart: 06/22/2022
Return: 06/28/2022

provided by Cheapoair.com

Multiple AirlinesColorado Springs To Las Vegas Multiple Airlines airfares from Colorado Springs in July
$6887 Depart: 07/05/2022
Return: 07/20/2022

provided by Cheapoair.com

 

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 [...]
San Juan Pictures
  • El Morro - San Juanview
  • San Juan, Puerto Rico - San Juanview
  • San Juan, Puerto Rico - San Juanview
  • El Morro - San Juanview
   Welcome to Travelgrove  register tell a friend bookmark it 
 
This airfare deal was found   ago. Click "Check price" to see current prices!
*