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 ($104), Frontier ($109), and United Airlines ($126).

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 - 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 cheapest flights from Chicago O'Hare Intl Airport to Caribbean Islands?

Looking at all options, your cheapest flight can be booked for $119. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $174 on average our data indicates $638 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 Air Canada (87%), United Airlines (87%) and Air New Zealand (87%).

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.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 43 days in advance, which can save you up to 43% on flights from Chicago O'Hare Intl Airport to Caribbean Islands compared to booking the week you need them. Waiting 43 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $293. For sooner than that we have options available in the next 3 days from $362.

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

September can be a great time to fly to Caribbean Islands from Chicago O'Hare Intl Airport with a flight ticket averaging about $379. Cheapflights users have found deals in the month of September for as cheap as $139. The most expensive prices can be found in the month of December.

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.

$104+ 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	$205 (Priceline)
One-way from	$104 (FlightHub)
Popular in	December
Cheapest in	September
Average price	$376

From Chicago O'Hare Intl to Caribbean Islands

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

Search Deals

Highest demand for flights based on searches. 12% potential increase in price ($55 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).

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Average for round-trip flights in July 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 julio 1, 2025.

mar. 8/511:28 amORD - SJU

1 stop29h 34mMultiple Airlines

mié. 8/133:55 pmSJU - ORD

Nonstop5h 04mMultiple Airlines

Deal found 6/29

$205

lun. 9/85:10 amORD - SJU

1 stop8h 01mFrontier

jue. 9/251:11 amSJU - ORD

1 stop11h 52mFrontier

Deal found 6/30

$207

dom. 7/205:05 amORD - SJU

1 stop15h 04mSpirit Airlines

sáb. 8/22:28 pmSJU - ORD

Nonstop5h 19mSpirit Airlines

Deal found 6/30

$213

lun. 8/114:37 pmORD - STT

2 stops18h 53mSpirit Airlines

mié. 8/202:43 pmSTT - ORD

1 stop8h 39mSpirit Airlines

Deal found 6/28

$255

jue. 8/148:34 pmORD - PUJ

1 stop15h 31mAmerican Airlines

jue. 8/213:30 pmPUJ - ORD

Nonstop5h 00mAmerican Airlines

Deal found 6/30

$306

mar. 7/295:05 amORD - PUJ

1 stop8h 25mSpirit Airlines

mar. 8/52:00 pmPUJ - ORD

2 stops34h 13mSpirit Airlines

Deal found 7/1

$310

jue. 8/145:01 amORD - PUJ

1 stop8h 09mMultiple Airlines

jue. 8/2112:40 pmPUJ - ORD

2 stops12h 19mMultiple Airlines

Deal found 6/30

$327

mar. 9/166:44 pmORD - SDQ

1 stop6h 11mSpirit Airlines

sáb. 9/272:12 pmSDQ - ORD

1 stop8h 46mSpirit Airlines

Deal found 6/30

$334

dom. 7/275:01 amORD - PUJ

1 stop8h 09mFrontier

vie. 8/13:24 pmPUJ - ORD

1 stop9h 58mFrontier

Deal found 6/30

$340

dom. 9/285:30 amORD - PUJ

1 stop6h 50mDelta

jue. 10/23:59 pmPUJ - ORD

1 stop8h 53mDelta

Deal found 6/30

$343

sáb. 8/95:01 amORD - AUA

1 stop8h 28mMultiple Airlines

sáb. 8/163:45 pmAUA - ORD

1 stop9h 14mMultiple Airlines

Deal found 6/30

$352

mié. 7/168:09 amORD - SDQ

1 stop7h 20mMultiple Airlines

mar. 8/53:35 pmSDQ - ORD

1 stop25h 36mMultiple Airlines

Deal found 7/1

$356

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 julio 1, 2025.

mar. 8/511:28 amORD - SJU

1 stop29h 34mMultiple Airlines

mié. 8/133:55 pmSJU - ORD

Nonstop5h 04mMultiple Airlines

Deal found 6/29

$205

lun. 9/85:10 amORD - SJU

1 stop8h 01mFrontier

jue. 9/251:11 amSJU - ORD

1 stop11h 52mFrontier

Deal found 6/30

$207

dom. 7/205:05 amORD - SJU

1 stop15h 04mSpirit Airlines

sáb. 8/22:28 pmSJU - ORD

Nonstop5h 19mSpirit Airlines

Deal found 6/30

$213

jue. 8/148:34 pmORD - PUJ

1 stop15h 31mAmerican Airlines

jue. 8/213:30 pmPUJ - ORD

Nonstop5h 00mAmerican Airlines

Deal found 6/30

$306

dom. 9/285:30 amORD - PUJ

1 stop6h 50mDelta

jue. 10/23:59 pmPUJ - ORD

1 stop8h 53mDelta

Deal found 6/30

$343

mar. 7/291:07 amORD - PUJ

1 stop10h 50mCopa Airlines

mié. 8/65:16 amPUJ - ORD

1 stop19h 30mCopa Airlines

Deal found 6/30

$347

dom. 9/286:45 amORD - NAS

1 stop6h 20mJetBlue

jue. 10/23:10 pmNAS - ORD

1 stop6h 40mJetBlue

Deal found 7/1

$437

jue. 9/113:50 pmORD - UVF

1 stop21h 25mAir Canada

mar. 9/233:10 pmUVF - ORD

1 stop27h 23mAir Canada

Deal found 7/1

$450

sáb. 11/153:05 pmORD - PLS

2 stops21h 40mSouthwest

jue. 11/202:40 pmPLS - ORD

1 stop8h 10mSouthwest

Deal found 6/30

$493

lun. 8/114:37 pmORD - STT

2 stops18h 53mSpirit Airlines

mié. 8/202:43 pmSTT - ORD

1 stop8h 39mSpirit Airlines

Deal found 6/28

$255

jue. 8/145:01 amORD - PUJ

1 stop8h 09mMultiple Airlines

jue. 8/2112:40 pmPUJ - ORD

2 stops12h 19mMultiple Airlines

Deal found 6/30

$327

dom. 7/275:01 amORD - PUJ

1 stop8h 09mFrontier

vie. 8/13:24 pmPUJ - ORD

1 stop9h 58mFrontier

Deal found 6/30

$340

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 julio 1, 2025 and is based on user searches.

mar. 7/88:41 pmORD - PUJ

1 stop14h 43mAmerican Airlines

mar. 7/153:31 pmPUJ - ORD

Nonstop5h 05mAmerican Airlines

Deal found 6/29

$324

mar. 7/84:45 pmORD - STT

1 stop16h 03mSpirit Airlines

mar. 7/154:05 pmSTT - ORD

1 stop8h 06mSpirit Airlines

Deal found 7/1

$373

mar. 7/85:01 amORD - SDQ

1 stop18h 27mMultiple Airlines

mar. 7/1510:55 amSDQ - ORD

1 stop13h 18mMultiple Airlines

Deal found 7/1

$413

mié. 7/96:23 pmORD - SJU

Nonstop4h 43mSpirit Airlines

jue. 7/1710:14 pmSJU - ORD

1 stop11h 41mSpirit Airlines

Deal found 6/30

$274

mié. 7/911:28 amORD - SDQ

1 stop22h 17mFrontier

dom. 7/131:48 amSDQ - ORD

1 stop23h 34mFrontier

Deal found 6/30

$406

jue. 7/106:16 pmORD - MBJ

1 stop13h 39mMultiple Airlines

mar. 7/1512:10 pmMBJ - ORD

2 stops11h 01mMultiple Airlines

Deal found 6/29

$416

vie. 7/114:26 pmORD - SJU

1 stop7h 06mMultiple Airlines

vie. 7/183:50 pmSJU - ORD

1 stop16h 14mMultiple Airlines

Deal found 6/29

$257

vie. 7/114:26 pmORD - SJU

1 stop7h 06mFrontier

vie. 7/185:00 pmSJU - ORD

1 stop7h 31mFrontier

Deal found 6/30

$271

vie. 7/114:26 pmORD - SXM

1 stop18h 02mMultiple Airlines

mié. 7/233:05 pmSXM - ORD

1 stop9h 08mMultiple Airlines

Deal found 6/30

$370

vie. 7/116:16 pmORD - AUA

1 stop19h 13mFrontier

sáb. 7/193:35 pmAUA - ORD

1 stop8h 54mFrontier

Deal found 7/1

$400

mar. 7/155:05 amORD - PUJ

1 stop8h 25mSpirit Airlines

sáb. 7/1912:40 pmPUJ - ORD

1 stop11h 47mSpirit Airlines

Deal found 6/30

$323

mar. 7/155:05 amORD - PUJ

1 stop8h 25mMultiple Airlines

lun. 7/219:04 pmPUJ - ORD

1 stop20h 07mMultiple Airlines

Deal found 6/30

$359

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 julio 1, 2025.

mar. 7/295:05 amORD - MBJ

1 stop6h 00mSpirit Airlines

Deal found 6/29

$104

vie. 8/15:01 amORD - MBJ

1 stop9h 44mFrontier

Deal found 6/29

$109

mié. 8/65:01 amORD - PUJ

1 stop8h 09mFrontier

Deal found 6/30

$113

mar. 8/125:01 amORD - SJU

1 stop8h 44mMultiple Airlines

Deal found 7/1

$114

mar. 7/154:36 pmORD - SJU

1 stop7h 59mSpirit Airlines

Deal found 6/30

$115

lun. 8/255:05 amORD - PUJ

1 stop8h 55mSpirit Airlines

Deal found 6/29

$117

lun. 9/19:32 amORD - SJU

1 stop13h 11mFrontier

Deal found 6/30

$123

mar. 8/129:23 amORD - PUJ

Nonstop4h 42mUnited Airlines

Deal found 6/30

$126

lun. 8/48:45 pmORD - PUJ

1 stop13h 16mAmerican Airlines

Deal found 6/30

$131

vie. 8/84:37 pmORD - STT

2 stops18h 53mSpirit Airlines

Deal found 7/1

$139

sáb. 8/165:01 amORD - AUA

1 stop8h 28mFrontier

Deal found 6/29

$143

sáb. 7/265:05 amORD - AUA

1 stop8h 35mSpirit Airlines

Deal found 7/1

$148

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

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 8/5

11:28 am-6:02 pm

1 stop29h 34m

San Juan Luis Munoz Marin Intl

mié. 8/13

3:55 pm-7:59 pm

Nonstop5h 04m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 9/8

5:10 am-2:11 pm

1 stop8h 01m

San Juan Luis Munoz Marin Intl

dom. 9/14

1:11 am-11:53 am

1 stop11h 42m

$207

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

dom. 7/20

5:05 am-9:09 pm

1 stop15h 04m

San Juan Luis Munoz Marin Intl

sáb. 8/2

2:28 pm-6:47 pm

Nonstop5h 19m

$213

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

lun. 8/11

4:37 pm-12:30 pm

2 stops18h 53m

Saint Thomas Island Cyril E King

mié. 8/20

2:43 pm-10:22 pm

1 stop8h 39m

$255

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

jue. 8/14

8:34 pm-1:05 pm

1 stop15h 31m

Punta Cana

jue. 8/21

3:30 pm-7:30 pm

Nonstop5h 00m

$306

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 7/29

5:05 am-2:30 pm

1 stop8h 25m

Punta Cana

mar. 8/5

2:00 pm-11:13 pm

2 stops34h 13m

$310

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

mar. 9/16

6:44 pm-1:55 am

1 stop6h 11m

Santo Domingo Las Americas

sáb. 9/27

2:12 pm-9:58 pm

1 stop8h 46m

$334

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

dom. 7/27

5:01 am-2:10 pm

1 stop8h 09m

Punta Cana

sáb. 8/2

3:25 pm-11:53 pm

1 stop9h 28m

$335

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

dom. 9/28

5:30 am-1:20 pm

1 stop6h 50m

Punta Cana

jue. 10/2

3:59 pm-11:52 pm

1 stop8h 53m

$343

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

sáb. 8/9

5:01 am-2:29 pm

1 stop8h 28m

Oranjestad Reina Beatrix

sáb. 8/16

3:45 pm-11:59 pm

1 stop9h 14m

$352

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

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 (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).

Reviews of airlines servicing Caribbean Islands

See what other customers who have flown with Southwest, Delta, and Copa 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.

Southwest

8.0

Very good

4,273 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Southwest

8.0

Very good

4,273 reviews

Southwest

8.0

Very good

4,273 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Delta

8.0

Very good

7,973 reviews

Southwest

8.0

Very good

4,273 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Copa Airlines

7.5

Good

1,465 reviews

Southwest

8.0

Very good

4,273 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Aeromexico

7.5

Good

1,718 reviews

Southwest

8.0

Very good

4,273 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

United Airlines

7.4

Good

8,858 reviews

Southwest

8.0

Very good

4,273 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 Spirit Airlines ($104), Frontier ($109), and United Airlines ($126).
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 Air Canada (87%), United Airlines (87%) and Air New Zealand (87%).
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 $119. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $174 on average our data indicates $638 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 10 airlines flying from O'Hare Intl to Caribbean Islands

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$106	Average$369	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$139	Average$381	FlexibilityNo cancel fee	On-time65%
Copa Airlines	Cheapest$193	Average$537	FlexibilityNo cancel fee	On-time70%
Delta	Cheapest$212	Average$608	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$226	Average$645	FlexibilityNo cancel fee	On-time69%
Arajet	Cheapest$235	Average$304	FlexibilityNo cancel fee	On-timeN/A
JetBlue	Cheapest$261	Average$488	FlexibilityNo cancel fee	On-time62%
Air Canada	Cheapest$335	Average$753	FlexibilityNo cancel fee	On-time67%
American Airlines	Cheapest$338	Average$644	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$385	Average$486	FlexibilityNo cancel fee	On-time63%

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$104+ 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 7/29. 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 julio 1, 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

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 julio 1, 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 julio 1, 2025.

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.

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.

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?

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 julio 1, 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 Southwest, Delta, and Copa 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.

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?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for O'Hare Intl to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.

Top 10 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 julio 1, 2025.