Cheap flights from Chicago to Caribbean

Travel > Caribbean

Travel tip: Visit Ponce on your holidays!

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 $158 / RT details

Book your flight now with Cheapoair.com and save!

Cheap Aguadilla airfares from $158/RT are provided by Cheapoair.com. Outbound flight is leaving on 04/19/2024, 03:44 pm from Chicago Midway (MDW) airport and arrives at Aguadilla Borinquen (BQN) at 01:45 am. The flight time is 10 hours and 1 minutes. The Returning flight departes on 04/25/2024, 02:45 am (other return dates are also available). Date posted: 04 Apr 2024

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

  • $158Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Aguadilla, PR (BQN)04/19/202403:44 pm
    Aguadilla, PR (BQN)Chicago, IL (MDW)04/25/202402:45 am
    cheapoair.com check price
  • $213Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)04/20/202408:25 am
    Aguadilla, PR (BQN)Chicago, IL (ORD)04/26/202402:45 am
    cheapoair.com check price
  • $242Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Santiago, DO (STI)04/20/202406:41 pm
    Santiago, DO (STI)Chicago, IL (ORD)05/04/202402:42 am
    cheapoair.com check price
  • $244Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)04/27/202408:25 am
    Aguadilla, PR (BQN)Chicago, IL (ORD)05/08/202402:45 am
    cheapoair.com check price
  • $252Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Aguadilla, PR (BQN)04/27/202408:17 pm
    Aguadilla, PR (BQN)Chicago, IL (MDW)05/08/202402:45 am
    cheapoair.com check price
  • $74Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)San Juan, PR (SJU)05/18/202405:45 pm
    cheapoair.com check price
  • $74Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Ponce, PR (PSE)04/25/202405:56 pm
    cheapoair.com check price
  • $80Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)04/27/202406:41 pm
    cheapoair.com check price
  • $84Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)San Juan, PR (SJU)04/28/202402:44 pm
    cheapoair.com check price
  • $85Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Punta Cana, DO (PUJ)05/12/202405:47 am
    cheapoair.com check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesSan Diego To Orlando Multiple Airlines airfares from San Diego in May
$291 Depart: 05/09/2024
Return: 05/23/2024

provided by Cheapoair.com

Multiple AirlinesWashington DC To La Paz Multiple Airlines airfares from Washington DC in May
$914 Depart: 05/01/2024
Return: 05/14/2024

provided by Cheapoair.com

Multiple AirlinesDenver To Chisinau Multiple Airlines airfares from Denver in December
$1053 Depart: 12/09/2023
Return: 12/24/2023

provided by Cheapoair.com

Multiple AirlinesDurham To San Francisco Multiple Airlines airfares from Durham in April
$344 Depart: 04/26/2024
Return: 05/06/2024

provided by Cheapoair.com

Multiple AirlinesDenver To Punta Cana Multiple Airlines airfares from Denver in May
$630 Depart: 05/04/2024
Return: 05/11/2024

provided by Cheapoair.com

Austrian AirlinesDenver To Bucharest Austrian Airlines airfares from Denver in March
$973 Depart: 03/08/2024
Return: 03/19/2024

provided by Cheapoair.com

Frontier AirlinesAtlanta To Houston Frontier Airlines airfares from Atlanta in April
$100 Depart: 04/30/2024
Return: 05/13/2024

provided by Cheapoair.com

WestjetMontreal To San Juan Westjet airfares from Montreal in October
$522 Depart: 10/26/2024
Return: 11/02/2024

provided by Cheapoair.com

Multiple AirlinesMinneapolis To Tunis Multiple Airlines airfares from Minneapolis in June
$1857 Depart: 06/04/2024
Return: 06/19/2024

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.

   Welcome to Travelgrove  register tell a friend bookmark it 
 
This airfare deal was found   ago. Click "Check price" to see current prices!
*