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?

Frontier, Spirit Airlines, and Arajet 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 November 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.

$86 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 day?

As of November 2025, 12 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.

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 87 per week as of November 2025. The most frequent departure day is Sun, with 18% of weekly flights leaving on this day.

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:15 pm - 10:47 amORD-SJU

13h 32m1 stop

2:38 pm - 6:00 pmSJU-ORD

5h 22mnonstop

$210Multiple Airlines

Find Deal

Fri, Feb 6 - Thu, Feb 19

8:20 am - 7:38 pmORD-SJU

9h 18m1 stop

1:59 am - 2:03 pmSJU-ORD

14h 04m1 stop

$211Multiple Airlines

Find Deal

Mon, Dec 1 - Sun, Dec 7

3:15 pm - 1:24 amORD-SJU

8h 09m1 stop

3:55 am - 4:19 pmSJU-ORD

14h 24m1 stop

$212Frontier

Find Deal

Mon, Mar 2 - Mon, Mar 2

10:00 am - 12:27 amORD-SJU

12h 27m1 stop

3:55 am - 1:31 pmSJU-ORD

11h 36m1 stop

$214Frontier

Find Deal

Fri, Nov 28 - Sat, Dec 6

5:45 am - 12:26 pmORD-SJU

4h 41mnonstop

2:38 pm - 6:00 pmSJU-ORD

5h 22mnonstop

$217Spirit Airlines

Find Deal

Wed, Jan 7 - Mon, Jan 12

2:20 pm - 9:00 pmORD-SJU

4h 40mnonstop

4:52 pm - 8:20 pmSJU-ORD

5h 28mnonstop

$218United Airlines

Find Deal

Mon, Jan 19 - Fri, Jan 23

8:41 am - 3:17 pmORD-SJU

4h 36mnonstop

6:00 am - 8:09 pmSJU-ORD

16h 09m1 stop

$219Spirit Airlines

Find Deal

Tue, Dec 2 - Tue, Dec 9

2:20 pm - 9:00 pmORD-SJU

4h 40mnonstop

2:05 am - 10:53 amSJU-ORD

10h 48m1 stop

$223United Airlines

Find Deal

Sun, Jan 25 - Tue, Jan 27

8:35 am - 3:18 pmORD-SJU

4h 43mnonstop

6:00 am - 9:35 amSJU-ORD

5h 35mnonstop

$243American Airlines

Find Deal

Sun, Jan 18 - Fri, Jan 23

5:18 am - 4:54 pmORD-STT

9h 36m1 stop

12:28 pm - 7:18 pmSTT-ORD

8h 50m1 stop

$251American Airlines

Find Deal

Sat, Nov 15 - Sat, Nov 22

Frontier flights from Chicago O'Hare Intl Airport to Caribbean

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

Frontier

Mar 2

ORD3:15 pmChicago O'Hare Intl

8h 09m

1 stop

SJU1:24 amSan Juan Luis Munoz Marin Intl

Mar 2

SJU3:55 amSan Juan Luis Munoz Marin Intl

14h 24m

1 stop

ORD4:19 pmChicago O'Hare Intl

$212

Find similar

Frontier

Nov 28

ORD10:00 amChicago O'Hare Intl

12h 27m

1 stop

SJU12:27 amSan Juan Luis Munoz Marin Intl

Dec 6

SJU3:55 amSan Juan Luis Munoz Marin Intl

11h 36m

1 stop

ORD1:31 pmChicago O'Hare Intl

$214

Find similar

Frontier

Jan 10

ORD6:11 pmChicago O'Hare Intl

14h 06m

1 stop

SJU10:17 amSan Juan Luis Munoz Marin Intl

Jan 13

SJU8:45 amSan Juan Luis Munoz Marin Intl

15h 14m

2 stops

ORD9:59 pmChicago O'Hare Intl

$215

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 7

ORD5:45 amChicago O'Hare Intl

4h 41m

SJU12:26 pmSan Juan Luis Munoz Marin Intl

Jan 12

SJU2:38 pmSan Juan Luis Munoz Marin Intl

5h 22m

ORD6:00 pmChicago O'Hare Intl

$217

Find similar

Spirit Airlines

Dec 2

ORD8:41 amChicago O'Hare Intl

4h 36m

SJU3:17 pmSan Juan Luis Munoz Marin Intl

Dec 9

SJU6:00 amSan Juan Luis Munoz Marin Intl

16h 09m

1 stop

ORD8:09 pmChicago O'Hare Intl

$219

Find similar

Spirit Airlines

Jan 6

ORD5:45 amChicago O'Hare Intl

4h 41m

SJU12:26 pmSan Juan Luis Munoz Marin Intl

Jan 14

SJU2:38 pmSan Juan Luis Munoz Marin Intl

5h 22m

ORD6:00 pmChicago O'Hare Intl

$228

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

Fri 2/6

7:15 pm-10:47 am

1 stop13h 32m

San Juan Luis Munoz Marin Intl

Thu 2/19

2:38 pm-6:00 pm

Nonstop5h 22m

$210

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 12/1

8:20 am-7:38 pm

1 stop9h 18m

San Juan Luis Munoz Marin Intl

Sun 12/7

1:59 am-2:03 pm

1 stop14h 04m

$211

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/2

3:15 pm-1:24 am

1 stop8h 09m

San Juan Luis Munoz Marin Intl

Mon 3/2

3:55 am-4:19 pm

1 stop14h 24m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 11/28

10:00 am-12:27 am

1 stop12h 27m

San Juan Luis Munoz Marin Intl

Sat 12/6

3:55 am-1:31 pm

1 stop11h 36m

$214

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/7

5:45 am-12:26 pm

Nonstop4h 41m

San Juan Luis Munoz Marin Intl

Mon 1/12

2:38 pm-6:00 pm

Nonstop5h 22m

$217

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 1/23

4:52 pm-8:20 pm

Nonstop5h 28m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 12/2

8:41 am-3:17 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

Tue 12/9

6:00 am-8:09 pm

1 stop16h 09m

$219

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/25

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Tue 1/27

2:05 am-10:53 am

1 stop10h 48m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/18

8:35 am-3:18 pm

Nonstop4h 43m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:00 am-9:35 am

Nonstop5h 35m

$243

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 11/15

5:18 am-4:54 pm

1 stop9h 36m

Saint Thomas Island Cyril E King

Sat 11/22

12:28 pm-7:18 pm

1 stop8h 50m

$251

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, January 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 $321. If you don’t want to visit Caribbean in January, then you should wait until April 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 Tuesday when prices can be found for as low as $392. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $444. 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 $314. 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 $450.

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

Fly from Chicago O'Hare Intl to Punta Cana 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 $389 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 $323 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?

No. A direct flight is the cheapest option for a flight between Chicago O'Hare Intl Airport to Caribbean.

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	$167
Fastest flight time	3h 18m
Direct flights	Every day
Airports in Caribbean	4 airports

The best one-way flight to Caribbean from Chicago O'Hare Intl Airport in the past 72 hours is $167. The best round-trip flight deal from Chicago O'Hare Intl Airport to Caribbean found on momondo in the last 72 hours is $355.

The fastest flight from Chicago O'Hare Intl Airport to Caribbean takes 3h 18m

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

There are 4 airports near Caribbean: 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 November 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 26.47% of all bookings. The subsequent popular models are Airbus A321neo at 21.47%, Boeing 737 MAX 8 at 16.14%, and Boeing 737-900 at 12.71%.

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 $106	Free Cancellation	Rating 5.8 3,117 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $140	Free Cancellation	Rating 6.3 8,116 reviews	Search Spirit Airlines flights
Delta	PriceFrom $186	Free Cancellation	Rating 7.9 8,001 reviews	Search Delta flights
Copa Airlines	PriceFrom $188	Free Cancellation	Rating 7.6 1,561 reviews	Search Copa Airlines flights
United Airlines	PriceFrom $226	Free Cancellation	Rating 7.4 8,997 reviews	Search United Airlines flights
Arajet	PriceFrom $233	Free Cancellation	Rating 7.1 36 reviews	Search Arajet flights
JetBlue	PriceFrom $261	Free Cancellation	Rating 7.2 2,907 reviews	Search JetBlue flights
American Airlines	PriceFrom $345	Free Cancellation	Rating 7.2 11,036 reviews	Search American Airlines flights
Southwest	PriceFrom $385	Free Cancellation	Rating 8.0 4,238 reviews	Search Southwest 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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Tue 12/2

Tue 12/9

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Caribbean

Popular cities in Caribbean

Flights to San Juanfrom $119

Flights to Punta Canafrom $205

Flights to Santo Domingofrom $186

Flights to Montego Bayfrom $221

Flights to Oranjestadfrom $180

Flights to Nassaufrom $257

Flights to Saint Thomas Islandfrom $184

Flights to Kingstonfrom $244

Flights to Simpson Bayfrom $230

Flights to Port of Spainfrom $282

Flights to Santiago de los Caballerosfrom $214

Flights to Willemstadfrom $307

Chicago O'Hare Intl Airport flight routes

Flights from Chicago O'Hare Intl to New York John F Kennedy Intl

Flights from Chicago O'Hare Intl to Nashville Intl

Flights from Chicago O'Hare Intl to Minneapolis St Paul

Flights from Chicago O'Hare Intl to Raleigh-Durham

Flights from Chicago O'Hare Intl to Charlotte Douglas

Flights from Chicago O'Hare Intl to Atlanta Hartsfield-Jackson

Cheap flights from Chicago O'Hare Intl Airport to Caribbean from $86

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

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

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Frontier flights from Chicago O'Hare Intl Airport to Caribbean

Our best Frontier 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

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

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 Punta Cana 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?

No. A direct flight is the cheapest option for a flight between Chicago O'Hare Intl Airport to Caribbean.

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

Frontier, Spirit Airlines, and Arajet 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 November 2025, 12 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 87 per week as of November 2025. The most frequent departure day is Sun, with 18% 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