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Caribbean Islands

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

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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Nov 5 — Nov 121
Tue 11/5
Tue 11/12
1 adult, Economy
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Find flight deals from O'Hare Intl to Caribbean Islands

Cheapest flights from O'Hare Intl to Caribbean Islands
Explore the most affordable flight options available from O'Hare Intl to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 31, 2024.

This FlightHub deal was found by Cheapflights users on 10/30. 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.
Fri 12/66:07 pmORD - SJU
1 stop21h 16mMultiple Airlines
Wed 12/112:17 pmSJU - ORD
Nonstop5h 30mMultiple Airlines
Deal found 10/30$169
This FareScan deal was found by Cheapflights users on 10/31. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/39:10 pmORD - SJU
1 stop12h 51mSpirit Airlines
Tue 12/1010:34 amSJU - ORD
1 stop11h 41mSpirit Airlines
Deal found 10/31$171
This FlightHub deal was found by Cheapflights users on 10/30. 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.
Thu 11/146:30 amORD - SJU
1 stop17h 19mFrontier
Sun 11/1710:12 pmSJU - ORD
1 stop15h 40mFrontier
Deal found 10/30$175
This Mytrip deal was found by Cheapflights users on 10/31. 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 11/165:00 amORD - PUJ
1 stop8h 46mMultiple Airlines
Wed 11/204:37 pmPUJ - ORD
Nonstop5h 28mMultiple Airlines
Deal found 10/31$287
This Mytrip deal was found by Cheapflights users on 10/29. 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.
Thu 11/1411:10 amORD - STT
2 stops21h 38mSpirit Airlines
Tue 11/1911:43 amSTT - ORD
1 stop8h 58mSpirit Airlines
Deal found 10/29$287
This Cheapflightsfares deal was found by Cheapflights users on 10/31. 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.
Sat 12/76:00 amORD - PUJ
Nonstop4h 29mFrontier
Thu 12/126:45 pmPUJ - ORD
Nonstop5h 14mFrontier
Deal found 10/31$288
This JetBlue deal was found by Cheapflights users on 10/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/88:51 amORD - SJU
1 stop7h 44mJetBlue
Tue 12/107:00 amSJU - ORD
1 stop10h 53mJetBlue
Deal found 10/30$289
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Mon 12/97:00 amORD - PUJ
1 stop7h 05mAmerican Airlines
Thu 12/125:50 pmPUJ - ORD
1 stop8h 24mAmerican Airlines
Deal found 10/30$336
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Mon 12/910:43 amORD - PUJ
Nonstop4h 28mUnited Airlines
Mon 12/165:25 pmPUJ - ORD
1 stop7h 55mUnited Airlines
Deal found 10/30$339
This Mytrip deal was found by Cheapflights users on 10/29. 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.
Mon 12/29:25 pmORD - STT
3 stops35h 26mMultiple Airlines
Mon 12/92:18 pmSTT - ORD
3 stops27h 48mMultiple Airlines
Deal found 10/29$363
This FareScan deal was found by Cheapflights users on 10/31. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/95:00 amORD - PUJ
1 stop8h 46mSpirit Airlines
Wed 11/134:51 pmPUJ - ORD
2 stops29h 24mSpirit Airlines
Deal found 10/31$364
This Delta deal was found by Cheapflights users on 10/30. 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.
Tue 11/127:10 amORD - PUJ
1 stop7h 30mDelta
Wed 11/203:44 pmPUJ - ORD
1 stop7h 31mDelta
Deal found 10/30$368

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

Customize your flight search to find flights from O'Hare Intl to Caribbean Islands 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 2,570,725 searches. Data last updated October 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/26

4:01 pm-2:38 am

1 stop8h 37m

$84

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 12/10

8:02 pm-5:43 pm

1 stop19h 41m

$89

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 11/9

4:24 pm-6:54 pm

2 stops24h 30m

$114

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 12/7

8:51 am-7:19 pm

1 stop8h 28m

$143

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 12/9

5:10 am-4:45 pm

1 stop9h 35m

$160

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 1/1

6:20 am-4:52 pm

1 stop8h 32m

$165

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

Wed 1/29

1:35 pm-10:00 am

1 stop18h 25m

$172

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 11/11

10:43 am-5:11 pm

Nonstop4h 28m

$176

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 12/2

6:00 am-12:37 pm

Nonstop4h 37m

$94

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/22

7:30 am-9:40 pm

2 stops12h 10m

$192

Flights are sorted by cheapest first

Deals found on 10/30

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

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from O'Hare Intl 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 O'Hare Intl to Caribbean Islands

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

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

Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean Islands (average of $254). Flying from Chicago O'Hare Intl Airport to Caribbean Islands in March is currently the most expensive (average of $335). 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?

Find hourly flight availability from O'Hare Intl to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 31, 2024.

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

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Caribbean Islands. Reviews last updated October 31, 2024.
Read reviews from past customers who have flown Frontier, Spirit Airlines and United Airlines from Chicago to Caribbean Islands. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,116 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,835 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,420 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Copa Airlines
7.8
Good
1,885 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,514 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Related info for your journey

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

  • Can I find flights from Chicago O'Hare Intl Airport to Caribbean Islands for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago O'Hare Intl Airport to Caribbean Islands for under $200. The cheapest flight booked recently is on Spirit Airlines for just $126, but on average you can expect to pay $305.

  • Are there nonstop flights from Chicago O'Hare Intl Airport to Caribbean Islands for under $200 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago O'Hare Intl Airport to Caribbean Islands under $200. A good price for a nonstop flight from Chicago O'Hare Intl Airport to Caribbean Islands is less than $527.

  • Are there last-minute flights available from Chicago O'Hare Intl Airport to Caribbean Islands for under $200?

    There are currently 20+ open flights from Chicago O'Hare Intl Airport to Caribbean Islands within the next 7 days for less than $200.

  • What days are nonstop flights available from Chicago O'Hare Intl Airport to Caribbean Islands?

    Nonstop flights can be found on the following days: Sunday, Thursday, Friday, Saturday.

  • How many flights depart from Chicago O'Hare Intl Airport to Caribbean Islands on average per day?

    2 flight departures from Chicago O'Hare Intl Airport to Caribbean Islands per day on average.
    Morning (6am - Noon) - 100% of flight departures

  • How long is the flight from Chicago O'Hare Intl Airport to Caribbean Islands?

    For as low as $126, Spirit Airlines can have you in Caribbean Islands from Chicago O'Hare Intl Airport in 4h 28m. The distance between Chicago O'Hare Intl Airport and Caribbean Islands is about 2085 mi. This flight may include one or multiple stops.

  • 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 Spirit Airlines ($68), Frontier ($69), and JetBlue ($143).

  • 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 Spirit Airlines (83%), Air Canada (45%) and United Airlines (45%).

  • 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 $83. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $135 on average our data indicates $735 when flying from Chicago O'Hare Intl Airport to Caribbean Islands.

  • What does ORD to SJU mean?

    Chicago O'Hare Intl Airport is ORD and San Juan Luis Munoz Marin Intl Airport is SJU. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Punta Cana Airport (PUJ), Santo Domingo Las Americas Airport (SDQ), Montego Bay Sangster Intl Airport (MBJ), Oranjestad Reina Beatrix Airport (AUA), Nassau Intl Airport (NAS) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from O'Hare Intl to Caribbean Islands that include extra baggage allowance?

    The amount of baggage you can bring on your O'Hare Intl to Caribbean Islands flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from O'Hare Intl to Caribbean Islands with specific airlines?

    Yes, Cheapflights allows you to browse and filter O'Hare Intl to Caribbean Islands flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from O'Hare Intl to Caribbean Islands that allow pets onboard?

    Many airlines flying from O'Hare Intl to Caribbean Islands offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from O'Hare Intl to Caribbean Islands?

    Yes, you can often find last-minute deals on O'Hare Intl to Caribbean Islands flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago O'Hare Intl Airport to Caribbean Islands flight deals updated?

    The Chicago O'Hare Intl Airport to Caribbean Islands flight deals you see on this page were last updated on 10/31.

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

    Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean Islands (average of $254). Flying from Chicago O'Hare Intl Airport to Caribbean Islands in March is currently the most expensive (average of $335). 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

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

Discover the top 8 airlines that operate flights from O'Hare Intl to Caribbean Islands. 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 2,570,725 searches. Data last updated October 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$117Average$341FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$159Average$419FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$173Average$564FlexibilityNo cancel feeOn-time62%
DeltaCheapest$204Average$547FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$268Average$620FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$325Average$631FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$379Average$524FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$526Average$880FlexibilityNo cancel feeOn-time67%
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