What airlines fly to Caribbean?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Caribbean from Chicago O'Hare Intl Airport according to our data. American Airlines is the first choice among our users, with 35% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 12 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago O'Hare Intl to Caribbean?

Spirit Airlines, Frontier, and JetBlue are the most popular carriers operating from Chicago O'Hare Intl to Caribbean

How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Caribbean?

As of December 2025, there are 11 operators available to choose from for flights from Chicago O'Hare Intl Airport to Caribbean.

How old do you have to be to fly from Chicago O'Hare Intl Airport to Caribbean?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Caribbean.

What documentation or ID do you need to fly to Caribbean?

The travel and health documents required for your trip to Caribbean can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$71 Cheap Flights from Chicago O'Hare Intl Airport to Caribbean in 2025/26

Q: How many flights depart from Chicago O'Hare Intl Airport to Caribbean on average per week?

The number of flights available between Chicago O'Hare Intl Airport and Caribbean is 183 per week as of December 2025. The most frequent departure day is Mon, with 15% of weekly flights leaving on this day.

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

As of December 2025, 26 flights take off from Chicago O'Hare Intl Airport and land in Caribbean each day. The most common flight departure time for this route is 8:00AM, with 73% of daily flights taking off at noon.

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Find the cheapest flights from Chicago O'Hare Intl Airport to Caribbean

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

9:18 am - 7:43 pm

ORD

SJU

8h 25m1 stop

5:25 pm - 11:15 pm

SJU

ORD

7h 50m1 stop

$195Multiple Airlines

Sat, Feb 21 - Mon, Mar 2

7:45 am - 6:05 pm

ORD

SJU

8h 20m1 stop

11:06 am - 7:36 pm

SJU

ORD

10h 30m1 stop

$196JetBlue

Tue, Jan 13 - Fri, Jan 23

12:17 pm - 6:49 pm

ORD

SJU

4h 32mnonstop

1:22 pm - 4:37 pm

SJU

ORD

5h 15mnonstop

$197Spirit Airlines

Sat, Jan 24 - Wed, Feb 4

9:25 am - 4:21 pm

ORD

SJU

28h 56m1 stop

5:25 pm - 3:52 pm

SJU

ORD

24h 27m1 stop

$198Frontier

Sat, Feb 7 - Tue, Feb 10

1:54 pm - 2:25 am

ORD

SJU

10h 31m1 stop

2:54 am - 9:11 am

SJU

ORD

8h 17m1 stop

$201Frontier

Thu, Feb 19 - Sun, Feb 22

8:43 pm - 2:10 pm

ORD

SXM

15h 27m1 stop

3:15 pm - 11:46 pm

SXM

ORD

10h 31m1 stop

$223Spirit Airlines

Fri, Jan 23 - Thu, Jan 29

5:45 am - 12:30 pm

ORD

PUJ

4h 45mnonstop

6:00 pm - 9:10 pm

PUJ

ORD

5h 10mnonstop

$249Arajet

Wed, Feb 25 - Sun, Mar 1

10:27 am - 5:12 pm

ORD

PUJ

4h 45mnonstop

5:47 am - 8:57 am

PUJ

ORD

5h 10mnonstop

$251Arajet

Sat, Feb 21 - Sat, Feb 28

10:22 am - 3:28 pm

ORD

MBJ

4h 06mnonstop

4:38 pm - 8:15 pm

MBJ

ORD

4h 37mnonstop

$377American Airlines

Sun, Mar 1 - Fri, Mar 6

5:00 am - 2:26 pm

ORD

MBJ

8h 26m1 stop

4:38 pm - 8:15 pm

MBJ

ORD

4h 37mnonstop

$381American Airlines

Sun, Mar 1 - Fri, Mar 6

JetBlue flights from Chicago O'Hare Intl Airport to Caribbean

Our best JetBlue deals on Chicago O'Hare Intl Airport to Caribbean flight tickets

JetBlue

Jan 13

ORD7:45 amChicago O'Hare Intl

8h 20m

1 stop

SJU6:05 pmSan Juan Luis Munoz Marin Intl

Jan 23

SJU11:06 amSan Juan Luis Munoz Marin Intl

10h 30m

1 stop

ORD7:36 pmChicago O'Hare Intl

$196

Find similar

JetBlue

Feb 27

ORD12:41 pmChicago O'Hare Intl

9h 03m

1 stop

SJU11:44 pmSan Juan Luis Munoz Marin Intl

Mar 7

SJU5:10 amSan Juan Luis Munoz Marin Intl

8h 48m

1 stop

ORD11:58 amChicago O'Hare Intl

$202

Find similar

JetBlue

Jan 31

ORD9:40 amChicago O'Hare Intl

7h 46m

1 stop

SJU7:26 pmSan Juan Luis Munoz Marin Intl

Feb 7

SJU1:30 pmSan Juan Luis Munoz Marin Intl

8h 15m

1 stop

ORD7:45 pmChicago O'Hare Intl

$205

Find similar

Spirit Airlines flights from Chicago O'Hare Intl Airport to Caribbean

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Caribbean flight tickets

Spirit Airlines

Jan 31

ORD12:17 pmChicago O'Hare Intl

4h 32m

SJU6:49 pmSan Juan Luis Munoz Marin Intl

Feb 6

SJU1:22 pmSan Juan Luis Munoz Marin Intl

5h 15m

ORD4:37 pmChicago O'Hare Intl

$197

Find similar

Spirit Airlines

Jan 9

ORD9:23 amChicago O'Hare Intl

7h 35m

1 stop

SJU6:58 pmSan Juan Luis Munoz Marin Intl

Jan 15

SJU11:52 amSan Juan Luis Munoz Marin Intl

8h 24m

1 stop

ORD6:16 pmChicago O'Hare Intl

$207

Find similar

Spirit Airlines

Feb 18

ORD10:44 amChicago O'Hare Intl

10h 25m

1 stop

SJU11:09 pmSan Juan Luis Munoz Marin Intl

Feb 25

SJU12:32 pmSan Juan Luis Munoz Marin Intl

5h 16m

ORD3:48 pmChicago O'Hare Intl

$220

Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

9:18 am-7:43 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Mon 3/2

5:25 pm-11:15 pm

1 stop7h 50m

$195

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 1/13

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Fri 1/23

11:06 am-7:36 pm

1 stop10h 30m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Wed 2/4

1:22 pm-4:37 pm

Nonstop5h 15m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/7

9:25 am-4:21 pm

1 stop28h 56m

San Juan Luis Munoz Marin Intl

Tue 2/10

5:25 pm-3:52 pm

1 stop24h 27m

$198

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 2/19

1:54 pm-2:25 am

1 stop10h 31m

San Juan Luis Munoz Marin Intl

Sun 2/22

2:54 am-9:11 am

1 stop8h 17m

$201

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/23

8:43 pm-2:10 pm

1 stop15h 27m

Simpson Bay Princess Juliana

Thu 1/29

3:15 pm-11:46 pm

1 stop10h 31m

$223

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 2/25

5:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Sun 3/1

6:00 pm-9:10 pm

Nonstop5h 10m

$249

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 2/21

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 2/28

5:47 am-8:57 am

Nonstop5h 10m

$251

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 3/1

10:22 am-3:28 pm

Nonstop4h 06m

Montego Bay Sangster Intl

Fri 3/6

4:38 pm-8:15 pm

Nonstop4h 37m

$377

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 3/1

5:00 am-2:26 pm

1 stop8h 26m

Montego Bay Sangster Intl

Fri 3/6

4:38 pm-8:15 pm

Nonstop4h 37m

$381

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Caribbean

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Caribbean?

In general, April is the cheapest month to fly from Chicago O'Hare Intl Airport to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $342. If you don’t want to visit Caribbean in April, then you should wait until January to fly from Chicago O'Hare Intl Airport, when ticket prices are also cheap, with an average price of $348.

What is the cheapest day to depart on your flight to Caribbean?

The cheapest day to depart from Chicago O'Hare Intl Airport to Caribbean is on a Monday when prices can be found for as low as $389. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $446. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

What is the cheapest time of day to depart on your flight to Caribbean?

In the evening is the cheapest time of day to fly from Chicago O'Hare Intl Airport to Caribbean when you can find flight prices for as low as $321. Flying to Caribbean in the evening is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $447.

What is the cheapest Chicago O'Hare Intl to Caribbean flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago O'Hare Intl - Caribbean flight prices

How far in advance should I book a flight to Caribbean?

You are more likely to see cheaper flights to Caribbean from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $395 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Chicago O'Hare Intl Airport for as low as $338 on momondo.

What cabin class options are available on Chicago O'Hare Intl to Caribbean flights?

There are 4 cabin classes available to choose from on Chicago O'Hare Intl to Caribbean flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago O'Hare Intl Airport to Caribbean flights?

You could potentially save up to 16% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Caribbean flight.

Cheap Chicago O'Hare Intl Airport to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Caribbean

Best Price Found	$153
Fastest flight time	3h 22m
Direct flights	Every day
Airports in Caribbean	195 airports

The best one-way flight to Caribbean from Chicago O'Hare Intl Airport in the past 72 hours is $153. The best round-trip flight deal from Chicago O'Hare Intl Airport to Caribbean found on momondo in the last 72 hours is $315.

The fastest flight from Chicago O'Hare Intl Airport to Caribbean takes 3h 22m

Direct flights go from Chicago O'Hare Intl Airport to Caribbean every day.

There are 195 airports in Caribbean. From Chicago O'Hare Intl Airport there are direct flights to George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Montego Bay Sangster Intl (MBJ), Providenciales (PLS).

Search flight deals

When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Caribbean?
Prices for flights from Chicago O'Hare Intl Airport to Caribbean refresh daily.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Caribbean?
As of December 2025, there are 11 operators available to choose from for flights from Chicago O'Hare Intl Airport to Caribbean.
How old do you have to be to fly from Chicago O'Hare Intl Airport to Caribbean?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents required for your trip to Caribbean can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago O'Hare Intl Airport to Caribbean?
momondo data reveals that the most frequently booked plane model on the route from Chicago O'Hare Intl Airport to Caribbean is Boeing 737-800, representing 25.01% of all bookings. The subsequent popular models are Airbus A321neo at 21.98%, Boeing 737 MAX 8 at 15.83%, and Boeing 737-900 at 11.46%.

Best airlines flying from Chicago O'Hare Intl Airport to Caribbean

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Caribbean with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $108	Free Cancellation	Rating 5.8 3,082 reviews	Search Frontier flights
JetBlue	PriceFrom $142	Free Cancellation	Rating 7.2 2,896 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom $145	Free Cancellation	Rating 6.3 8,191 reviews	Search Spirit Airlines flights
Delta	PriceFrom $186	Free Cancellation	Rating 7.9 8,007 reviews	Search Delta flights
Copa Airlines	PriceFrom $188	Free Cancellation	Rating 7.6 1,556 reviews	Search Copa Airlines flights
United Airlines	PriceFrom $215	Free Cancellation	Rating 7.4 9,091 reviews	Search United Airlines flights
Arajet	PriceFrom $236	Free Cancellation	Rating 6.8 38 reviews	Search Arajet flights
Southwest	PriceFrom $277	Free Cancellation	Rating 7.9 4,249 reviews	Search Southwest flights
Air Canada	PriceFrom $335	Free Cancellation	Rating 7.1 10,534 reviews	Search Air Canada flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Caribbean?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Caribbean for you.

Can I find flights from Chicago to Caribbean with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Caribbean from Chicago with this policy.

How can momondo help me find flights from Chicago to Caribbean?

Once all potential Chicago to Caribbean flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Caribbean right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Caribbean, momondo offers a useful price alert feature which will track prices for flights to Caribbean from Chicago and alert you when they change.

An easier way to manage your Caribbean trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Cheap flights from Chicago O'Hare Intl Airport to Caribbean from $71

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Find the cheapest flights from Chicago O'Hare Intl Airport to Caribbean

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JetBlue flights from Chicago O'Hare Intl Airport to Caribbean

Our best JetBlue deals on Chicago O'Hare Intl Airport to Caribbean flight tickets

Spirit Airlines flights from Chicago O'Hare Intl Airport to Caribbean

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Caribbean flight tickets

momondo Fare Finder

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

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Caribbean

What is the cheapest month to fly to Caribbean?

What is the cheapest day to depart on your flight to Caribbean?

What is the cheapest time of day to depart on your flight to Caribbean?

What is the cheapest Chicago O'Hare Intl to Caribbean flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago O'Hare Intl - Caribbean flight prices

How far in advance should I book a flight to Caribbean?

What cabin class options are available on Chicago O'Hare Intl to Caribbean flights?

There are 4 cabin classes available to choose from on Chicago O'Hare Intl to Caribbean flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago O'Hare Intl Airport to Caribbean flights?

You could potentially save up to 16% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Caribbean flight.

What is the cheapest airline that flies from Chicago O'Hare Intl to Caribbean?

Spirit Airlines, Frontier, and JetBlue are the most popular carriers operating from Chicago O'Hare Intl to Caribbean

What airlines fly to Caribbean?

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

As of December 2025, 26 flights take off from Chicago O'Hare Intl Airport and land in Caribbean each day. The most common flight departure time for this route is 8:00AM, with 73% of daily flights taking off at noon.

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

The number of flights available between Chicago O'Hare Intl Airport and Caribbean is 183 per week as of December 2025. The most frequent departure day is Mon, with 15% of weekly flights leaving on this day.

Cheap Chicago O'Hare Intl Airport to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Caribbean

Best Price Found

Fastest flight time

Direct flights

Airports in Caribbean

When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Caribbean?

How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Caribbean?

How old do you have to be to fly from Chicago O'Hare Intl Airport to Caribbean?

What documentation or ID do you need to fly to Caribbean?

What is the most popular plane model from Chicago O'Hare Intl Airport to Caribbean?

Best airlines flying from Chicago O'Hare Intl Airport to Caribbean

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Caribbean with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Caribbean?

Can I find flights from Chicago to Caribbean with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Caribbean?

I’m not ready to book a flight from Chicago to Caribbean right now. Can momondo alert me if prices change?

An easier way to manage your Caribbean trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Caribbean

Popular cities in Caribbean

Popular flights according to clicks in the last 7 days on momondo