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Cheap flights from Chicago O'Hare Intl Airport to Caribbean from $84

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to Caribbean departing on 9/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago O'Hare Intl Airport to Caribbean

Cheap round-trip flights

Spirit Airlines Logo
11:36 am - 1:48 pmORD-STT
25h 12m2 stops
Spirit Airlines Logo
2:43 pm - 11:59 pmSTT-ORD
10h 16m2 stops
$189Spirit Airlines
Find Deal
Wed, Aug 27 - Wed, Sep 3
Spirit Airlines Logo
5:05 am - 9:48 pmORD-SJU
15h 43m1 stop
Spirit Airlines Logo
10:16 pm - 9:22 amSJU-ORD
12h 06m1 stop
$190Spirit Airlines
Find Deal
Sun, Aug 17 - Fri, Aug 22
Spirit Airlines Logo
11:36 am - 1:48 pmORD-STT
25h 12m2 stops
Spirit Airlines Logo
2:43 pm - 11:59 pmSTT-ORD
10h 16m2 stops
$199Spirit Airlines
Find Deal
Sat, Aug 23 - Sat, Aug 30
Frontier Logo
7:46 pm - 8:59 amORD-SJU
12h 13m1 stop
Frontier Logo
3:39 am - 3:17 pmSJU-ORD
12h 38m1 stop
$238Frontier
Find Deal
Sat, Aug 30 - Fri, Sep 5
Frontier Logo
8:00 am - 2:34 amORD-SJU
17h 34m1 stop
Frontier Logo
3:39 am - 3:17 pmSJU-ORD
12h 38m1 stop
$245Frontier
Find Deal
Sat, Sep 6 - Fri, Sep 12
United Airlines Logo
7:35 am - 4:30 pmORD-GCM
7h 55m1 stop
United Airlines Logo
2:50 pm - 6:04 pmGCM-ORD
4h 14mnonstop
$510United Airlines
Find Deal
Sun, Dec 14 - Fri, Dec 19
American Airlines Logo
8:10 am - 12:56 pmORD-GCM
3h 46mnonstop
American Airlines Logo
2:00 pm - 5:10 pmGCM-ORD
4h 10mnonstop
$513American Airlines
Find Deal
Mon, Jan 12 - Wed, Jan 21
American Airlines Logo
6:30 am - 4:31 pmORD-GCM
9h 01m2 stops
American Airlines Logo
2:00 pm - 5:10 pmGCM-ORD
4h 10mnonstop
$514American Airlines
Find Deal
Sun, Dec 14 - Fri, Dec 19
Delta Logo
5:40 am - 12:30 pmORD-GCM
5h 50m1 stop
Delta Logo
3:45 pm - 11:58 pmGCM-ORD
9h 13m1 stop
$520Delta
Find Deal
Wed, Dec 24 - Wed, Dec 31
Delta Logo
7:59 pm - 12:30 pmORD-GCM
15h 31m1 stop
Delta Logo
3:45 pm - 11:58 pmGCM-ORD
9h 13m1 stop
$545Delta
Find Deal
Mon, Dec 22 - Mon, Dec 29

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
Aug 30
ORD7:46 pmChicago O'Hare Intl
12h 13m
1 stop
SJU8:59 amSan Juan Luis Munoz Marin Intl
Sep 5
SJU3:39 amSan Juan Luis Munoz Marin Intl
12h 38m
1 stop
ORD3:17 pmChicago O'Hare Intl
$238
Find similar
Frontier
Aug 9
ORD12:20 pmChicago O'Hare Intl
11h 07m
1 stop
SJU12:27 amSan Juan Luis Munoz Marin Intl
Aug 16
SJU3:08 pmSan Juan Luis Munoz Marin Intl
9h 21m
1 stop
ORD11:29 pmChicago O'Hare Intl
$239
Find similar
Frontier
Sep 6
ORD8:00 amChicago O'Hare Intl
17h 34m
1 stop
SJU2:34 amSan Juan Luis Munoz Marin Intl
Sep 12
SJU3:39 amSan Juan Luis Munoz Marin Intl
12h 38m
1 stop
ORD3:17 pmChicago O'Hare Intl
$245
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
Aug 27
ORD11:36 amChicago O'Hare Intl
25h 12m
2 stops
STT1:48 pmSaint Thomas Island Cyril E King
Sep 3
STT2:43 pmSaint Thomas Island Cyril E King
10h 16m
2 stops
ORD11:59 pmChicago O'Hare Intl
$189
Find similar
Spirit Airlines
Aug 17
ORD5:05 amChicago O'Hare Intl
15h 43m
1 stop
SJU9:48 pmSan Juan Luis Munoz Marin Intl
Aug 22
SJU10:16 pmSan Juan Luis Munoz Marin Intl
12h 06m
1 stop
ORD9:22 amChicago O'Hare Intl
$190
Find similar
Spirit Airlines
Aug 23
ORD11:36 amChicago O'Hare Intl
25h 12m
2 stops
STT1:48 pmSaint Thomas Island Cyril E King
Aug 30
STT2:43 pmSaint Thomas Island Cyril E King
10h 16m
2 stops
ORD11:59 pmChicago O'Hare Intl
$199
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to Caribbean 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, momondo users made 832,500 searches. Data last updated August 3, 2025.
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

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 8/27

11:36 am-1:48 pm

2 stops25h 12m

Saint Thomas Island Cyril E King

Wed 9/3

2:43 pm-11:59 pm

2 stops10h 16m

$189

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/17

5:05 am-9:48 pm

1 stop15h 43m

San Juan Luis Munoz Marin Intl

Fri 8/22

10:16 pm-9:22 am

1 stop12h 06m

$190

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 8/23

11:36 am-1:48 pm

2 stops25h 12m

Saint Thomas Island Cyril E King

Sat 8/30

2:43 pm-11:59 pm

2 stops10h 16m

$199

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/30

7:46 pm-8:59 am

1 stop12h 13m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-3:17 pm

1 stop12h 38m

$238

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 9/6

8:00 am-2:34 am

1 stop17h 34m

San Juan Luis Munoz Marin Intl

Fri 9/12

3:39 am-3:17 pm

1 stop12h 38m

$245

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/14

7:35 am-4:30 pm

1 stop7h 55m

George Town Owen Roberts Intl

Fri 12/19

2:50 pm-6:04 pm

Nonstop4h 14m

$510

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 1/12

8:10 am-12:56 pm

Nonstop3h 46m

George Town Owen Roberts Intl

Wed 1/21

2:00 pm-5:10 pm

Nonstop4h 10m

$513

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/14

6:30 am-4:31 pm

2 stops9h 01m

George Town Owen Roberts Intl

Fri 12/19

2:00 pm-5:10 pm

Nonstop4h 10m

$514

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/24

5:40 am-12:30 pm

1 stop5h 50m

George Town Owen Roberts Intl

Wed 12/31

3:45 pm-11:58 pm

1 stop9h 13m

$520

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 12/22

7:59 pm-12:30 pm

1 stop15h 31m

George Town Owen Roberts Intl

Mon 12/29

3:45 pm-11:58 pm

1 stop9h 13m

$545

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

In general, August 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 $314. If you don’t want to visit Caribbean in August, then you should wait until September to fly from Chicago O'Hare Intl Airport, when ticket prices are also cheap, with an average price of $316.

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 $395. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $449. 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 $303. 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 $444.

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 $375 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 $303 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 21% 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

$84

Fastest flight time

3h 25m

Direct flights

Every day

Airports in Caribbean

8 airports
The best one-way flight to Caribbean from Chicago O'Hare Intl Airport in the past 72 hours is $84. The best round-trip flight deal from Chicago O'Hare Intl Airport to Caribbean found on momondo in the last 72 hours is $189.
The fastest flight from Chicago O'Hare Intl Airport to Caribbean takes 3h 25m
Direct flights go from Chicago O'Hare Intl Airport to Caribbean every day.
There are 8 airports near Caribbean: George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Saint Thomas Island Cyril E King (STT), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Castries Hewanorra (UVF), Providenciales (PLS), San Juan Luis Munoz Marin Intl (SJU)
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?

  • 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?

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
FrontierPriceFrom $106Free CancellationRating
5.8
3,231 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,053 reviews
Search Spirit Airlines flights
DeltaPriceFrom $190Free CancellationRating
8.0
7,986 reviews
Search Delta flights
Copa AirlinesPriceFrom $193Free CancellationRating
7.5
1,496 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,909 reviews
Search United Airlines flights
ArajetPriceFrom $235Free CancellationRating
6.9
33 reviews
Search Arajet flights
JetBluePriceFrom $261Free CancellationRating
7.2
2,915 reviews
Search JetBlue flights
Air CanadaPriceFrom $335Free CancellationRating
7.1
9,874 reviews
Search Air Canada flights
American AirlinesPriceFrom $346Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $389Free CancellationRating
8.0
4,246 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.
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Find better results for your trip to Caribbean

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