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O'Hare Intl

$68+ Cheap flights from Caribbean Islands to O'Hare Intl (ORD)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
ene. 27 — feb. 31
lun. 1/27
lun. 2/3
1 adult, Economy
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Cheap flight deals from Caribbean Islands to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Caribbean Islands (zzEPX) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 22, 2025.

Round-trip from

$136
(eDestinos)

One-way from

$68
(FlightHub)
From Caribbean Islands to Chicago O'Hare Intl
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One-way flight from Caribbean Islands to Chicago O'Hare Intl
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Find flight deals from Caribbean Islands to O'Hare Intl

Cheapest flights from Caribbean Islands to O'Hare Intl
Explore the most affordable flight options available from Caribbean Islands to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 22, 2025.

This eDestinos deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/207:57 pmSJU - ORD
Nonstop5h 23mSpirit Airlines
lun. 2/2412:55 pmORD - SJU
Nonstop4h 31mSpirit Airlines
Deal found 1/22$136
This FlightHub deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/276:35 amSJU - ORD
1 stop8h 45mFrontier
mar. 3/43:14 pmORD - SJU
1 stop16h 35mFrontier
Deal found 1/22$137
This Kiwi.com deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/218:31 pmSJU - ORD
Nonstop5h 24mMultiple Airlines
lun. 2/247:08 pmORD - SJU
1 stop12h 41mMultiple Airlines
Deal found 1/22$142
This American Airlines deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 1/298:05 amSJU - ORD
1 stop10h 35mAmerican Airlines
lun. 2/311:53 amORD - SJU
1 stop10h 05mAmerican Airlines
Deal found 1/22$235
This Expedia deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/42:48 pmMBJ - ORD
1 stop8h 15mSpirit Airlines
mar. 3/115:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
Deal found 1/22$248
This Cheapflightsfares deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 1/306:54 pmPUJ - ORD
Nonstop5h 17mFrontier
mar. 2/46:10 amORD - PUJ
Nonstop4h 50mFrontier
Deal found 1/21$251
This Kiwi.com deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 1/306:19 pmSDQ - ORD
1 stop7h 13mSpirit Airlines
jue. 2/66:55 amORD - SDQ
1 stop8h 19mSpirit Airlines
Deal found 1/22$288
This Kiwi.com deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/712:51 pmSDQ - ORD
1 stop9h 22mMultiple Airlines
sáb. 2/158:44 pmORD - SDQ
2 stops14h 24mMultiple Airlines
Deal found 1/22$313
This eDestinos deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/134:48 pmPUJ - ORD
1 stop9h 10mSpirit Airlines
dom. 2/167:13 pmORD - PUJ
1 stop15h 29mSpirit Airlines
Deal found 1/21$319
This OneTravel deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/56:10 pmPUJ - ORD
Nonstop5h 17mMultiple Airlines
mié. 3/125:10 amORD - PUJ
1 stop8h 32mMultiple Airlines
Deal found 1/22$322
This Kiwi.com deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/137:43 pmSTI - ORD
1 stop30h 12mMultiple Airlines
mié. 2/1912:55 pmORD - STI
1 stop27h 28mMultiple Airlines
Deal found 1/21$365
This Booking.com deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/112:00 pmSDQ - ORD
1 stop29h 53mFrontier
mié. 7/910:57 amORD - SDQ
1 stop22h 41mFrontier
Deal found 1/22$412

Find flights from Caribbean Islands to O'Hare Intl within your budget

Customize your flight search to find flights from Caribbean Islands to O'Hare Intl that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated enero 22, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 2/20

7:57 pm-11:20 pm

Nonstop5h 23m

Chicago O'Hare Intl

lun. 2/24

12:55 pm-7:26 pm

Nonstop4h 31m

$136

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 2/27

6:35 am-1:20 pm

1 stop8h 45m

Chicago O'Hare Intl

mar. 3/4

3:14 pm-9:49 am

1 stop16h 35m

$137

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 2/21

8:31 pm-11:55 pm

Nonstop5h 24m

Chicago O'Hare Intl

lun. 2/24

7:08 pm-9:49 am

1 stop12h 41m

$142

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 3/4

2:48 pm-10:03 pm

1 stop8h 15m

Chicago O'Hare Intl

mar. 3/11

5:10 am-11:02 am

1 stop5h 52m

$248

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mié. 2/5

6:10 pm-9:27 pm

Nonstop5h 17m

Chicago O'Hare Intl

lun. 2/17

6:10 am-1:00 pm

Nonstop4h 50m

$262

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 2/13

4:48 pm-11:58 pm

1 stop9h 10m

Chicago O'Hare Intl

mar. 2/18

6:10 am-1:00 pm

Nonstop4h 50m

$294

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

vie. 2/7

12:51 pm-8:13 pm

1 stop9h 22m

Chicago O'Hare Intl

sáb. 2/15

8:44 pm-1:08 pm

2 stops14h 24m

$313

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

vie. 2/7

12:51 pm-8:13 pm

1 stop9h 22m

Chicago O'Hare Intl

sáb. 2/15

3:14 pm-3:26 pm

1 stop22h 12m

$331

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

sáb. 2/15

4:48 pm-11:58 pm

1 stop9h 10m

Chicago O'Hare Intl

vie. 2/21

5:00 am-3:43 pm

1 stop8h 43m

$337

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

jue. 2/13

7:43 pm-11:55 pm

1 stop30h 12m

Chicago O'Hare Intl

mié. 2/19

12:55 pm-6:23 pm

1 stop27h 28m

$365

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

Showing 1-10 of 60 results
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Best time to book a flight from Caribbean Islands to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Caribbean Islands with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Caribbean Islands to O'Hare Intl

Get recent, data-driven insights about flights from Caribbean Islands to O'Hare Intl including ideal travel times, pricing trends, and more.

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

Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Chicago O'Hare Intl Airport (average of $245). Flying from Caribbean Islands to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $320). 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 EPX to ORD?

Find hourly flight availability from Caribbean Islands to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated enero 22, 2025.

When flying from Caribbean Islands to Chicago O'Hare Intl Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Caribbean Islands to Chicago O'Hare Intl Airport

Explore weekly flight availability from Caribbean Islands to O'Hare Intl. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated enero 22, 2025.

The most flights from zzEPX to ORD are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'Hare Intl. Reviews last updated enero 22, 2025.
Get a feel of what it's like to fly with Spirit Airlines, United Airlines and Delta from Caribbean Islands to Chicago by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,654 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,514 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,707 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Copa Airlines
7.7
Good
1,659 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Aeromexico
7.5
Good
1,848 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $68. Users have also found prices from $70 and $123 on Spirit Airlines and United Airlines, respectively.

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

    When deciding which route to take from Caribbean Islands to Chicago O'Hare Intl Airport consider San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl, Nassau Intl - Chicago O'Hare Intl or Santo Domingo Las Americas - Chicago O'Hare Intl as they are the most popular.

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

    No one likes to see their flight delayed. When booking a flight from Caribbean Islands to Chicago O'Hare Intl Airport consider choosing Spirit Airlines (85%), Air Canada (83%) or United Airlines (83%) as they are the most reliable in getting you off to your destination on time.

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

    While on average a flight from Caribbean Islands to Chicago O'Hare Intl Airport is generally $815, our data shows the cheapest flight currently is $109. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $132 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean Islands to O'Hare Intl 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 Caribbean Islands to Chicago O'Hare Intl Airport?

    Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Chicago O'Hare Intl Airport (average of $245). Flying from Caribbean Islands to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $320). 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.

See more FAQs

Traveling to a place near Caribbean Islands?

Book flights to Caribbean Islands if you plan to visit one of these locations
Naperville
Rosemont
Beloit
Racine
Hoffman Estates
Schaumburg
Rockford
Skokie
Tinley Park
Arlington Heights
Northbrook
Evanston
Des Plaines
Orland Park
Merrillville
Kenosha
Lake Geneva
New Buffalo
Gurnee
Willowbrook

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Caribbean Islands to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Caribbean Islands to O'Hare Intl

Discover the top 8 airlines that operate flights from Caribbean Islands to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated enero 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$140Average$338FlexibilityNo cancel feeOn-time65%
FrontierCheapest$146Average$306FlexibilityNo cancel feeOn-time62%
DeltaCheapest$187Average$445FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$196Average$545FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$389FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$274Average$460FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$327Average$558FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$568FlexibilityNo cancel feeOn-time70%
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