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

For as low as $336, Spirit Airlines can have you in Caribbean Islands from Chicago O'Hare Intl Airport in 4h. The distance between Chicago O'Hare Intl Airport and Caribbean Islands is about 1613 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 Arajet ($94), United Airlines ($123), and Spirit Airlines ($124).

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.

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).

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 - Montego Bay Sangster Intl or Chicago O'Hare Intl - Punta Cana when deciding on the best route from Chicago O'Hare Intl Airport to Caribbean Islands.

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 $101. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $191 on average, our data indicates $848 when flying 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 American Airlines (78%), Alaska Airlines (78%) and Spirit Airlines (77%).

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

The most popular airlines flying from Chicago O'Hare Intl Airport to Caribbean Islands are American Airlines, JetBlue and Delta. Something to consider prior to booking your flight.

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.

$92+ Cheap Flights from Chicago O'Hare Intl Airport to Caribbean Islands

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Cheap flight deals from O'Hare Intl to Caribbean Islands

Round-trip from	$197 (Frontier)
One-way from	$92 (Cheapflightsfares)
Popular in	December
Cheapest in	October
Average price	$348

From Chicago O'Hare Intl to Caribbean Islands

Search Deals

One-way flight from Chicago O'Hare Intl to Caribbean Islands

Search Deals

Highest demand for flights based on searches. 8% potential increase in price ($36 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).

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Average for round-trip flights in October 2025

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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 6, 2025.

Mon 10/276:40 amORD - SJU

1 stop7h 44mFrontier

Fri 10/319:30 amSJU - ORD

2 stops15h 09mFrontier

Deal found 10/4

$197

Sat 10/258:40 amORD - SJU

1 stop9h 18mFrontier

Wed 10/299:00 amSJU - ORD

2 stops16h 12mFrontier

Deal found 10/5

$198

Tue 10/286:40 amORD - SJU

1 stop10h 14mFrontier

Tue 11/49:00 amSJU - ORD

1 stop29h 45mFrontier

Deal found 10/5

$201

Tue 10/286:40 amORD - SJU

1 stop10h 14mFrontier

Mon 11/39:00 amSJU - ORD

1 stop29h 45mFrontier

Deal found 10/4

$204

Sat 10/258:40 amORD - SJU

1 stop9h 18mMultiple Airlines

Fri 10/319:30 amSJU - ORD

1 stop23h 48mMultiple Airlines

Deal found 10/3

$206

Wed 10/227:43 pmORD - SJU

1 stop14h 13mSpirit Airlines

Wed 10/293:19 pmSJU - ORD

1 stop7h 14mSpirit Airlines

Deal found 10/3

$209

Sat 10/258:40 amORD - SJU

1 stop9h 18mFrontier

Tue 11/49:00 amSJU - ORD

1 stop29h 45mFrontier

Deal found 10/3

$212

Wed 10/226:40 amORD - SJU

1 stop7h 44mFrontier

Thu 10/233:19 pmSJU - ORD

1 stop9h 20mFrontier

Deal found 10/4

$213

Sat 10/258:40 amORD - SJU

1 stop9h 18mFrontier

Fri 10/313:31 pmSJU - ORD

1 stop9h 08mFrontier

Deal found 10/5

$214

Wed 10/226:40 amORD - SJU

1 stop18h 22mFrontier

Wed 10/299:00 amSJU - ORD

1 stop28h 45mFrontier

Deal found 10/5

$215

Mon 11/38:00 amORD - SJU

Nonstop4h 36mSpirit Airlines

Fri 11/73:41 pmSJU - ORD

Nonstop5h 10mSpirit Airlines

Deal found 10/4

$216

Sun 10/267:43 pmORD - STT

1 stop13h 13mSpirit Airlines

Thu 10/302:40 pmSTT - ORD

1 stop7h 53mSpirit Airlines

Deal found 10/5

$239

Best flights from O'Hare Intl to Caribbean Islands
Discover carefully curated flight deals from O'Hare Intl to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 6, 2025.

Mon 11/310:52 amORD - STT

1 stop24h 08mSpirit Airlines

Mon 11/101:55 pmSTT - ORD

1 stop21h 52mSpirit Airlines

Deal found 10/5

$293

Wed 12/311:25 amORD - SJU

1 stop10h 29mJetBlue

Wed 1/2811:15 amSJU - ORD

1 stop10h 30mJetBlue

Deal found 10/2

$333

Thu 2/58:45 amORD - GCM

Nonstop4h 00mUnited Airlines

Thu 2/122:25 pmGCM - ORD

1 stop9h 48mUnited Airlines

Deal found 10/5

$336

Sun 12/77:53 pmORD - PUJ

1 stop15h 20mDelta

Sat 12/135:19 pmPUJ - ORD

1 stop7h 24mDelta

Deal found 10/4

$338

Mon 2/27:50 pmORD - PLS

1 stop14h 51mAmerican Airlines

Fri 2/63:36 pmPLS - ORD

2 stops16h 46mAmerican Airlines

Deal found 10/5

$361

Mon 11/2412:50 pmORD - PLS

1 stop27h 50mAir Canada

Thu 11/276:40 pmPLS - ORD

2 stops25h 15mAir Canada

Deal found 10/4

$384

Tue 12/21:45 pmORD - SJU

2 stops8h 50mSouthwest

Sat 1/3111:45 amSJU - ORD

2 stops12h 05mSouthwest

Deal found 10/2

$390

Thu 11/276:45 pmORD - STT

2 stops17h 45mMultiple Airlines

Tue 12/23:25 pmSTT - ORD

1 stop26h 38mMultiple Airlines

Deal found 10/5

$394

Fri 10/317:43 pmORD - STT

1 stop13h 13mSpirit Airlines

Tue 11/41:55 pmSTT - ORD

1 stop12h 32mSpirit Airlines

Deal found 10/4

$317

Sat 11/87:20 pmORD - PUJ

1 stop16h 06mDelta

Fri 11/143:50 pmPUJ - ORD

1 stop8h 06mDelta

Deal found 10/4

$338

Mon 10/278:55 amORD - SJU

Nonstop4h 45mUnited Airlines

Sat 11/13:52 pmSJU - ORD

Nonstop5h 28mUnited Airlines

Deal found 10/5

$342

Sun 12/77:53 pmORD - PUJ

1 stop16h 32mDelta

Wed 12/105:04 pmPUJ - ORD

2 stops18h 56mDelta

Deal found 10/4

$342

Thu 10/302:20 pmORD - SJU

Nonstop4h 40mUnited Airlines

Sun 11/28:10 amSJU - ORD

Nonstop5h 22mUnited Airlines

Deal found 10/3

$342

Wed 11/195:00 amORD - SXM

2 stops9h 22mAmerican Airlines

Wed 11/265:24 pmSXM - ORD

2 stops16h 51mAmerican Airlines

Deal found 10/4

$380

Sun 10/266:00 amORD - STT

1 stop6h 35mSpirit Airlines

Sat 11/111:01 amSTT - ORD

2 stops24h 55mSpirit Airlines

Deal found 10/4

$368

Sat 12/66:10 pmORD - PUJ

2 stops17h 22mDelta

Thu 12/116:10 pmPUJ - ORD

1 stop16h 24mDelta

Deal found 10/4

$342

Wed 11/121:45 pmORD - SJU

2 stops8h 50mSouthwest

Tue 11/183:55 pmSJU - ORD

1 stop7h 55mSouthwest

Deal found 10/5

$418

Fri 10/318:55 amORD - SJU

Nonstop4h 45mUnited Airlines

Mon 11/32:05 amSJU - ORD

1 stop9h 00mUnited Airlines

Deal found 10/2

$347

Sat 11/156:45 amORD - UVF

1 stop30h 12mJetBlue

Sat 11/226:24 pmUVF - ORD

1 stop30h 22mJetBlue

Deal found 10/5

$422

Thu 11/2712:55 pmORD - STT

1 stop23h 35mSpirit Airlines

Tue 12/23:25 pmSTT - ORD

1 stop26h 38mSpirit Airlines

Deal found 10/5

$375

Sun 12/77:53 pmORD - PUJ

1 stop15h 20mDelta

Thu 12/112:57 pmPUJ - ORD

2 stops23h 13mDelta

Deal found 10/4

$342

Tue 11/45:00 amORD - GCM

1 stop5h 56mAmerican Airlines

Sat 11/89:00 amGCM - ORD

1 stop9h 15mAmerican Airlines

Deal found 10/2

$417

Tue 12/166:00 amORD - NAS

1 stop6h 33mUnited Airlines

Sat 12/204:05 pmNAS - ORD

Nonstop3h 57mUnited Airlines

Deal found 10/4

$368

Sun 12/75:59 pmORD - PUJ

1 stop17h 14mDelta

Fri 12/122:57 pmPUJ - ORD

2 stops21h 25mDelta

Deal found 10/4

$342

Thu 2/52:05 pmORD - UVF

1 stop23h 10mJetBlue

Tue 2/104:40 pmUVF - ORD

1 stop22h 30mJetBlue

Deal found 10/5

$481

Mon 11/105:00 amORD - SXM

1 stop6h 50mAmerican Airlines

Thu 11/135:24 pmSXM - ORD

2 stops15h 57mAmerican Airlines

Deal found 10/4

$438

Mon 12/159:08 pmORD - NAS

1 stop15h 25mUnited Airlines

Sat 12/204:05 pmNAS - ORD

Nonstop3h 57mUnited Airlines

Deal found 10/4

$368

Fri 12/58:40 pmORD - PUJ

1 stop15h 40mDelta

Thu 12/116:10 pmPUJ - ORD

2 stops17h 50mDelta

Deal found 10/4

$342

Sat 10/257:43 pmORD - STT

2 stops16h 52mSpirit Airlines

Sat 11/111:01 amSTT - ORD

2 stops24h 55mSpirit Airlines

Deal found 10/4

$428

Sat 12/64:20 pmORD - PUJ

2 stops19h 12mDelta

Fri 12/125:04 pmPUJ - ORD

1 stop17h 30mDelta

Deal found 10/4

$342

Last-minute flights from O'Hare Intl to Caribbean Islands
Discover last-minute flight deals from O'Hare Intl to Caribbean Islands. Data last updated October 6, 2025 and is based on user searches.

Wed 10/227:43 pmORD - SJU

1 stop14h 13mSpirit Airlines

Wed 10/293:19 pmSJU - ORD

1 stop7h 14mSpirit Airlines

Deal found 10/3

$209

Wed 10/226:40 amORD - SJU

1 stop7h 44mFrontier

Thu 10/233:19 pmSJU - ORD

1 stop9h 20mFrontier

Deal found 10/4

$213

Wed 10/226:40 amORD - SJU

1 stop18h 22mMultiple Airlines

Wed 10/299:00 amSJU - ORD

2 stops17h 03mMultiple Airlines

Deal found 10/5

$215

Sat 10/258:40 amORD - SJU

1 stop9h 18mFrontier

Wed 10/299:00 amSJU - ORD

2 stops16h 12mFrontier

Deal found 10/5

$198

Sat 10/258:40 amORD - SJU

1 stop9h 18mMultiple Airlines

Fri 10/319:30 amSJU - ORD

1 stop23h 48mMultiple Airlines

Deal found 10/3

$206

Sat 10/258:40 amORD - SJU

1 stop9h 18mFrontier

Tue 11/49:00 amSJU - ORD

1 stop29h 45mFrontier

Deal found 10/3

$212

Sat 10/258:40 amORD - SJU

1 stop9h 18mFrontier

Fri 10/313:31 pmSJU - ORD

1 stop9h 08mFrontier

Deal found 10/5

$214

Sun 10/267:43 pmORD - STT

1 stop13h 13mSpirit Airlines

Thu 10/302:40 pmSTT - ORD

1 stop7h 53mSpirit Airlines

Deal found 10/5

$239

Mon 10/276:40 amORD - SJU

1 stop7h 44mFrontier

Fri 10/319:30 amSJU - ORD

2 stops15h 09mFrontier

Deal found 10/4

$197

Tue 10/286:40 amORD - SJU

1 stop10h 14mFrontier

Tue 11/49:00 amSJU - ORD

1 stop29h 45mFrontier

Deal found 10/5

$201

Tue 10/286:40 amORD - SJU

1 stop10h 14mFrontier

Mon 11/39:00 amSJU - ORD

1 stop29h 45mFrontier

Deal found 10/5

$204

Mon 11/38:00 amORD - SJU

Nonstop4h 36mSpirit Airlines

Fri 11/73:41 pmSJU - ORD

Nonstop5h 10mSpirit Airlines

Deal found 10/4

$216

One-way flights from O'Hare Intl to Caribbean Islands
Search for one-way flight options from O'Hare Intl to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated October 6, 2025.

Wed 11/197:00 amORD - PUJ

Nonstop4h 35mFrontier

Deal found 10/4

$92

Sat 12/67:00 amORD - PUJ

Nonstop4h 37mFrontier

Deal found 10/5

$93

Sat 11/1510:27 amORD - PUJ

Nonstop4h 45mArajet

Deal found 10/5

$94

Sat 10/257:43 pmORD - STT

1 stop13h 13mSpirit Airlines

Deal found 10/5

$97

Tue 11/186:40 amORD - SJU

1 stop9h 14mFrontier

Deal found 10/4

$107

Mon 12/86:55 amORD - SJU

Nonstop4h 38mSpirit Airlines

Deal found 10/5

$108

Sat 11/812:17 pmORD - SJU

1 stop18h 28mMultiple Airlines

Deal found 10/4

$109

Sun 10/2610:27 amORD - SJU

1 stop8h 29mMultiple Airlines

Deal found 10/5

$111

Sat 11/86:40 amORD - SJU

1 stop9h 14mFrontier

Deal found 10/2

$112

Wed 11/196:40 amORD - SJU

1 stop18h 53mFrontier

Deal found 10/3

$113

Wed 2/45:45 amORD - PUJ

Nonstop4h 45mArajet

Deal found 10/5

$115

Wed 10/296:40 amORD - SJU

1 stop10h 14mFrontier

Deal found 10/2

$115

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Mon 11/3

10:52 am-1:00 pm

1 stop24h 08m

Saint Thomas Island Cyril E King

Mon 11/10

1:55 pm-9:47 am

1 stop21h 52m

$293

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 10/31

7:43 pm-9:56 am

1 stop13h 13m

Saint Thomas Island Cyril E King

Tue 11/4

1:55 pm-12:27 am

1 stop12h 32m

$317

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 12/3

11:25 am-11:54 pm

1 stop10h 29m

San Juan Luis Munoz Marin Intl

Wed 1/28

11:15 am-7:45 pm

1 stop10h 30m

$333

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 2/5

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Thu 2/12

2:25 pm-11:13 pm

1 stop9h 48m

$336

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 12/7

7:53 pm-1:13 pm

1 stop15h 20m

Punta Cana

Sat 12/13

5:19 pm-10:43 pm

1 stop7h 24m

$338

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 11/8

7:20 pm-1:26 pm

1 stop16h 06m

Punta Cana

Fri 11/14

3:50 pm-9:56 pm

1 stop8h 06m

$338

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 10/27

8:55 am-2:40 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Sat 11/1

3:52 pm-8:20 pm

Nonstop5h 28m

$342

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 12/7

7:53 pm-2:25 pm

1 stop16h 32m

Punta Cana

Wed 12/10

5:04 pm-10:00 am

2 stops18h 56m

$342

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 10/30

2:20 pm-8:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Sun 11/2

8:10 am-11:32 am

Nonstop5h 22m

$342

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 12/6

6:10 pm-1:32 pm

2 stops17h 22m

Punta Cana

Thu 12/11

6:10 pm-8:34 am

1 stop16h 24m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/5

Showing 1-10 of 60 results

...

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.

Cheapflights Insights

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

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 June is currently the most expensive (average of $339). 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?

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.

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

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

Reviews of airlines servicing Caribbean Islands

See what other customers who have flown with Delta, United Airlines, and American 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.

Delta

8.0

Very good

7,970 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Delta

8.0

Very good

7,970 reviews

Delta

8.0

Very good

7,970 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

United Airlines

7.4

Good

8,953 reviews

Delta

8.0

Very good

7,970 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

American Airlines

7.2

Good

11,041 reviews

Delta

8.0

Very good

7,970 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Spirit Airlines

6.3

Okay

8,077 reviews

Delta

8.0

Very good

7,970 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Frontier

5.8

Fair

3,147 reviews

Delta

8.0

Very good

7,970 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

How long is the flight from Chicago O'Hare Intl Airport to Caribbean Islands?
For as low as $336, Spirit Airlines can have you in Caribbean Islands from Chicago O'Hare Intl Airport in 4h. The distance between Chicago O'Hare Intl Airport and Caribbean Islands is about 1613 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 Arajet ($94), United Airlines ($123), and Spirit Airlines ($124).
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 - Montego Bay Sangster Intl or Chicago O'Hare Intl - Punta Cana 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 American Airlines (78%), Alaska Airlines (78%) and Spirit Airlines (77%).
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 $101. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $191 on average, our data indicates $848 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, 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 June is currently the most expensive (average of $339). 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

Browse thousands of different options on Cheapflights for your next trip

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

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$106	Average$508	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$139	Average$396	FlexibilityNo cancel fee	On-time65%
Copa Airlines	Cheapest$188	Average$431	FlexibilityNo cancel fee	On-time70%
Delta	Cheapest$196	Average$613	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$215	Average$653	FlexibilityNo cancel fee	On-time69%
Arajet	Cheapest$232	Average$313	FlexibilityNo cancel fee	On-timeN/A
JetBlue	Cheapest$261	Average$477	FlexibilityNo cancel fee	On-time62%
American Airlines	Cheapest$350	Average$645	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$385	Average$478	FlexibilityNo cancel fee	On-time63%

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$92+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from O'Hare Intl to Caribbean Islands with Cheapflights

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Cheap flight deals from O'Hare Intl to Caribbean Islands

Keep the following information in mind while searching for O'Hare Intl to Caribbean Islands flight deals. Data was last updated October 6, 2025.

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Find flight deals from O'Hare Intl to Caribbean Islands

Cheapest flights from O'Hare Intl to Caribbean IslandsExplore 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 6, 2025.

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 6, 2025.

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Best time to book a flight from O'Hare Intl to Caribbean Islands

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

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

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 6, 2025.

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

Reviews of airlines servicing Caribbean Islands

See what other customers who have flown with Delta, United Airlines, and American 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.

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.

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

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

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

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

What are the cheapest flights 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?

How can I 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?

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

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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

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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 6, 2025.