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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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Dec 28 — Jan 41
Sat 12/28
Sat 1/4
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 December 23, 2024.

Round-trip from

$148
(Frontier)

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 December 23, 2024.

This eDestinos deal was found by Cheapflights users on 12/22. 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.
Mon 12/304:00 pmSJU - ORD
1 stop29h 14mFrontier
Thu 1/27:29 pmORD - SJU
1 stop22h 26mFrontier
Deal found 12/22$261
This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/318:31 pmSJU - ORD
Nonstop5h 27mSpirit Airlines
Mon 1/68:14 pmORD - SJU
1 stop11h 33mSpirit Airlines
Deal found 12/22$277
This Booking.com deal was found by Cheapflights users on 12/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/288:31 pmSJU - ORD
Nonstop5h 27mMultiple Airlines
Mon 1/610:59 amORD - SJU
1 stop13h 50mMultiple Airlines
Deal found 12/21$280
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
Mon 12/3011:04 amSDQ - ORD
1 stop7h 02mSpirit Airlines
Wed 1/15:00 amORD - SDQ
1 stop10h 51mSpirit Airlines
Deal found 12/22$289
This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/302:43 pmSTT - ORD
1 stop9h 10mSpirit Airlines
Wed 1/85:11 pmORD - STT
1 stop15h 35mSpirit Airlines
Deal found 12/22$339
This Mytrip deal was found by Cheapflights users on 12/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/282:55 pmSDQ - ORD
1 stop11h 01mFrontier
Thu 1/210:15 pmORD - SDQ
1 stop11h 28mFrontier
Deal found 12/22$398
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
Mon 12/3011:04 amSDQ - ORD
1 stop7h 02mMultiple Airlines
Wed 1/110:22 pmORD - SDQ
2 stops17h 29mMultiple Airlines
Deal found 12/22$405
This American Airlines deal was found by Cheapflights users on 12/23. 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.
Wed 12/251:30 amSJU - ORD
1 stop8h 55mAmerican Airlines
Mon 12/309:55 amORD - SJU
1 stop12h 00mAmerican Airlines
Deal found 12/23$424
This United Airlines deal was found by Cheapflights users on 12/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/282:50 pmPUJ - ORD
Nonstop5h 10mUnited Airlines
Mon 1/138:50 amORD - PUJ
1 stop7h 08mUnited Airlines
Deal found 12/22$427
This Delta deal was found by Cheapflights users on 12/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/283:50 pmPUJ - ORD
1 stop7h 30mDelta
Mon 1/137:05 amORD - PUJ
1 stop6h 20mDelta
Deal found 12/22$428
This Southwest deal was found by Cheapflights users on 12/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/255:35 amSJU - ORD
2 stops11h 25mSouthwest
Tue 12/3111:25 amORD - SJU
2 stops11h 20mSouthwest
Deal found 12/22$454
This American Airlines deal was found by Cheapflights users on 12/22. 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.
Wed 12/256:00 amSDQ - ORD
2 stops12h 09mAmerican Airlines
Wed 1/16:37 amORD - SDQ
1 stop10h 13mAmerican Airlines
Deal found 12/22$457

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 December 23, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 1/29

9:15 pm-9:27 am

1 stop14h 12m

Chicago O'Hare Intl

Sun 2/2

4:18 pm-2:19 am

1 stop8h 01m

$150

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/20

7:57 pm-11:20 pm

Nonstop5h 23m

Chicago O'Hare Intl

Sat 2/22

12:54 pm-7:25 pm

Nonstop4h 31m

$151

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/23

9:26 pm-12:51 am

Nonstop5h 25m

Chicago O'Hare Intl

Mon 1/27

5:28 pm-2:19 am

1 stop6h 51m

$153

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 2/20

11:41 am-11:58 pm

1 stop14h 17m

Chicago O'Hare Intl

Tue 2/25

2:29 pm-1:38 pm

2 stops21h 09m

$229

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/8

3:10 pm-7:25 pm

Nonstop5h 15m

Chicago O'Hare Intl

Tue 5/13

8:05 am-1:45 pm

Nonstop4h 40m

$230

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 2/19

2:05 am-10:46 am

1 stop10h 41m

Chicago O'Hare Intl

Sat 2/22

1:20 pm-10:22 pm

1 stop7h 02m

$282

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 1/22

2:38 pm-8:13 pm

1 stop6h 35m

Chicago O'Hare Intl

Wed 1/29

5:11 am-1:33 pm

1 stop7h 22m

$283

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 2/5

1:16 pm-11:32 pm

1 stop11h 16m

Chicago O'Hare Intl

Wed 2/12

7:10 am-1:36 pm

1 stop5h 26m

$292

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 2/27

4:48 pm-11:58 pm

1 stop9h 10m

Chicago O'Hare Intl

Sun 3/2

7:13 pm-12:42 pm

1 stop15h 29m

$307

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 1/22

1:45 pm-12:09 am

2 stops11h 24m

Chicago O'Hare Intl

Wed 1/29

8:05 am-6:50 pm

2 stops9h 45m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/23

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 $317). 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 December 23, 2024.

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 December 23, 2024.

The most flights from zzEPX to ORD are scheduled on a Monday (10 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 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 December 23, 2024.
Get a feel of what it's like to fly with Delta, Frontier and Spirit Airlines 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
4,780 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Entertainment

7.7

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
4,780 reviews
Southwest
8.1
Very good
4,780 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Entertainment

7.7

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
8,588 reviews
Southwest
8.1
Very good
4,780 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Entertainment

7.7

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
1,712 reviews
Southwest
8.1
Very good
4,780 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Entertainment

7.7

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
1,913 reviews
Southwest
8.1
Very good
4,780 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Entertainment

7.7

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.

LATAM Airlines
7.5
Good
1,865 reviews
Southwest
8.1
Very good
4,780 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Entertainment

7.7

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 $117 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 American Airlines (90%), Alaska Airlines (90%) or Spirit Airlines (88%) 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 $416, our data shows the cheapest flight currently is $65. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $129 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 $317). 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 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 December 23, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$146Average$304FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$148Average$344FlexibilityNo cancel feeOn-time65%
DeltaCheapest$187Average$452FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$196Average$548FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$389FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$306Average$570FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$521FlexibilityNo cancel feeOn-time70%
JetBlueCheapest$467Average$619FlexibilityNo cancel feeOn-time62%
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