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Caribbean Islands

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

ORD — SJU
Nov 29 — Dec 61
Sun 11/29
Sun 12/6
1 adult, Economy
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Popular in

December

Cheapest in

August

Average price

$398
Highest demand for flights based on searches. 9% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Caribbean Islands

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Caribbean Islands?

To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Caribbean Islands, you should look to book at least 48 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Caribbean Islands?

Currently, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean Islands (average of $573). Flying from Chicago O'Hare Intl Airport to Caribbean Islands in December is currently the most expensive (average of $749). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to EPX?

One of the essential ways to save on airfare from Chicago O'Hare Intl Airport to Caribbean Islands is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 36% on airfare.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Caribbean Islands?

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Caribbean Islands flight should consider departing on Sunday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Caribbean Islands

See what other customers who have flown with United Airlines,JetBlue, andAmerican Airlines from Chicago O'Hare Intl Airport to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.3
Good
10,451 reviews

Comfort

7.3

Food

6.7

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.3

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
United Airlines
7.3
Good
10,451 reviews
United Airlines
7.3
Good
10,451 reviews

Comfort

7.3

Food

6.7

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.3

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
JetBlue
7.1
Good
3,076 reviews
United Airlines
7.3
Good
10,451 reviews

Comfort

7.3

Food

6.7

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.3

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
American Airlines
7.0
Good
12,208 reviews
United Airlines
7.3
Good
10,451 reviews

Comfort

7.3

Food

6.7

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.3

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
Frontier
5.5
Fair
2,515 reviews
United Airlines
7.3
Good
10,451 reviews

Comfort

7.3

Food

6.7

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.3

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible

Related info for your journey

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

    The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Caribbean Islands are JetBlue ($75), Frontier ($79), and Arajet ($102).

  • What are the most popular routes from Chicago O'Hare Intl Airport to Caribbean Islands?

    Most travelers choose Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago O'Hare Intl - Punta Cana or Chicago O'Hare Intl - Montego Bay Sangster Intl when deciding on the best route from Chicago O'Hare Intl Airport to Caribbean Islands.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Caribbean Islands?

    The top 3 most reliable airlines when flying from Chicago O'Hare Intl Airport to Caribbean Islands are Frontier (83%), United Airlines (82%) and Air New Zealand (82%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Caribbean Islands?

    Looking at all options, your cheapest flight can be booked for $129. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $195 on average, our data indicates $939 when flying from Chicago O'Hare Intl Airport to Caribbean Islands.

  • Can I find deals for flights from O'Hare Intl to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Caribbean Islands.

  • Can I find deals for business class flights from O'Hare Intl to Caribbean Islands?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Caribbean Islands?

    Currently, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean Islands (average of $573). Flying from Chicago O'Hare Intl Airport to Caribbean Islands in December is currently the most expensive (average of $749). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for O'Hare Intl to Caribbean Islands

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Top 9 airlines flying from O'Hare Intl to Caribbean Islands

AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$118Average$538FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$118Average$477FlexibilityNo cancel feeOn-time62%
FrontierCheapest$153Average$442FlexibilityNo cancel feeOn-time62%
ArajetCheapest$229Average$379FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$235Average$458FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$262Average$638FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$284Average$635FlexibilityNo cancel feeOn-time71%
Hahn AirCheapest$318Average$486FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$377Average$568FlexibilityNo cancel feeOn-time63%

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