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Cheap flights from Chicago-O'Hare Intl (ORD) to Caribbean

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How to find the cheapest flight from
Chicago-O'Hare Intl (ORD) to Caribbean

How far in advance should I book a flight from Chicago-O'Hare Intl to Caribbean?

Users have found that booking a flight from Chicago-O'Hare Intl to Caribbean at least 41 days early can save you up to 11% on average compared to booking a flight this week. If booking 41 days before your flight isn’t an option for you, users have found flights from Chicago-O'Hare Intl to Caribbean for as little as $380 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $415 for flights departing within the next 3 days.

What is the cheapest month to fly from Chicago-O'Hare Intl to Caribbean?

Flights from Chicago-O'Hare Intl to Caribbean lean towards being more expensive in December. Prices are generally better when you fly from Chicago-O'Hare Intl to Caribbean in September, with the cheapest ticket starting at $194.

Cheap flights from Chicago-O'Hare Intl to Caribbean in August, September 2020

The best prices found for ORD to Caribbean flights for August, September
28 Jul - 6 Aug
$75pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
26 Aug - 29 Aug
$76pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
29 Jul - 1 Aug
$80pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl

Chicago-O'Hare Intl to Caribbean 2020 flight deals

Cheap flights to Caribbean from Chicago-O'Hare Intl found for this year
28 Jul - 31 Jul
$75pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
26 Aug - 29 Aug
$76pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
29 Jul - 1 Aug
$80pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl

Non-stop flights to Caribbean from Chicago-O'Hare Intl

Save time with Chicago-O'Hare Intl to Caribbean direct flight deals
7 Sep - 15 Sep
$229pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
5 Sep - 13 Sep
$254pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
30 Nov - 12 Dec
$259pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago-O'Hare Intl to Caribbean

Late deals on round-trip flights to Caribbean from Chicago-O'Hare Intl, departing today and this week
28 Jul - 6 Aug
$75pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
23 Jul - 4 Aug
$76pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
25 Jul - 28 Jul
$81pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl

One-way flights to Caribbean from Chicago-O'Hare Intl

The cheapest one-way flights from Chicago-O'Hare Intl to Caribbean
2:30 am - 9:49 am
Multiple Airlines
1 Stop
30h 19m
ORD - SJU
Multiple Airlines
$78
Kiwi.com
1:00 pm - 8:42 am
Spirit Airlines
1 Stop
18h 42m
ORD - SJU
Spirit Airlines
$79
KAYAK
1:09 am - 11:36 am
JetBlue
1 Stop
9h 27m
ORD - SJU
JetBlue

Related info for your journey

Useful info, stats and facts about Chicago-O'Hare Intl to Caribbean flights.

Flight FAQs

From Chicago-O'Hare Intl to Caribbean

Are flight prices decreasing from Chicago-O'Hare Intl to Caribbean due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago-O'Hare Intl and Caribbean for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from Chicago-O'Hare Intl to Caribbean for under $100 on Cheapflights?

Yes, there are multiple flights from Chicago-O'Hare Intl to Caribbean for under $100. The cheapest flight booked recently is on Spirit Airlines for just $75, but on average you can expect to pay $89.

Are there nonstop flights from Chicago-O'Hare Intl to Caribbean for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago-O'Hare Intl to Caribbean under $300. A good price for a nonstop flight from Chicago-O'Hare Intl to Caribbean is less than $312.

Are there last-minute flights available from Chicago-O'Hare Intl to Caribbean for under $100?

There are currently 20+ open flights from Chicago-O'Hare Intl to Caribbean within the next 7 days for less than $100.

What days are nonstop flights available from Chicago-O'Hare Intl to Caribbean?

Days when nonstop flights are available for this flight are: Thursday.

What are the most popular airlines that fly from Chicago-O'Hare Intl to Caribbean?

When booking a flight from Chicago-O'Hare Intl to Caribbean, you may want to consider flying on Major Airline, American Airlines or Alaska Airlines as they are the most popular for this route.

What are the most popular routes from Chicago-O'Hare Intl to Caribbean?

Most travelers choose Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago O'Hare Intl - Montego Bay Sangster Intl or Chicago O'Hare Intl - Saint Thomas Island Cyril E King when deciding on the best route from Chicago-O'Hare Intl to Caribbean.

What are the cheapest Flights from Chicago-O'Hare Intl to Caribbean?

On average you can expect to pay $302 for a flight from Chicago-O'Hare Intl to Caribbean. The cheapest flight overall is $122 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $75.

How long is the flight from Chicago-O'Hare Intl to Caribbean?

There are many flights that can get you from Chicago-O'Hare Intl to Caribbean in 3h 47m. Fly via Japan Airlines, JetBlue, or Spirit Airlines to get the fastest option. This flight may include one or multiple stops.

What is the cheapest airline to fly from Chicago-O'Hare Intl to Caribbean round-trip?

Our cheapest airline available from Chicago-O'Hare Intl to Caribbean is Spirit Airlines. Our recent data shows that you can find tickets from as low as $75 on this airline.

What are the cheapest airlines to fly from Chicago-O'Hare Intl to Caribbean one-way?

To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $38. Spirit Airlines is not the only option available. At the moment, JetBlue is another option, for $80.

Arrival points for flights from Chicago-O'Hare Intl to Caribbean

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Destination information for Caribbean

Things to know before you go. Useful info for your trip from Chicago-O'Hare Intl to Caribbean
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Airports servicing Chicago

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