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Cheap flights from Chicago O'Hare Intl Airport to Caribbean from $88

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 8/4. 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

Enter your travel dates to find the best prices.
American Airlines Logo
5:14 pm - 11:07 pm
ORD
-
SJU
4h 53mnonstop
American Airlines Logo
7:14 pm - 9:00 am
SJU
-
ORD
14h 46m
1 stop
$222American Airlines
Sun, Aug 23 - Wed, Aug 26
Delta Logo
6:40 am - 4:37 pm
ORD
-
SJU
8h 57m
1 stop
Delta Logo
5:45 pm - 11:57 pm
SJU
-
ORD
7h 12m
1 stop
$226Delta
Wed, Aug 19 - Wed, Sep 2
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
6:00 am - 12:25 pm
SJU
-
ORD
7h 25m
1 stop
$228Frontier
Fri, Aug 14 - Sat, Aug 22
Frontier Logo
12:29 am - 6:26 am
ORD
-
SJU
4h 57mnonstop
Frontier Logo
5:12 pm - 3:26 pm
SJU
-
ORD
23h 14m
1 stop
$229Frontier
Sat, Sep 5 - Thu, Sep 10
JetBlue Logo
7:00 am - 1:48 pm
ORD
-
NAS
5h 48m
1 stop
JetBlue Logo
3:02 pm - 11:44 pm
NAS
-
ORD
9h 42m
1 stop
$284JetBlue
Tue, Aug 11 - Thu, Aug 20
JetBlue Logo
7:00 am - 5:14 pm
ORD
-
NAS
9h 14m
1 stop
JetBlue Logo
3:02 pm - 11:44 pm
NAS
-
ORD
9h 42m
1 stop
$303JetBlue
Sat, Aug 8 - Wed, Aug 19
Arajet Logo
12:12 pm - 5:57 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
$366Arajet
Sat, Aug 22 - Sat, Aug 29
Arajet Logo
5:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
6:10 pm - 9:20 pm
PUJ
-
ORD
5h 10mnonstop
$371Arajet
Fri, Nov 6 - Sun, Nov 15
Air Canada Logo
8:20 pm - 10:00 am
ORD
-
GCM
13h 40m
1 stop
Air Canada Logo
10:55 am - 9:00 am
GCM
-
ORD
22h 05m
1 stop
$403Air Canada
Fri, Jun 5 - Sat, Jun 13
Air Canada Logo
6:22 pm - 11:25 am
ORD
-
GCM
41h 03m
2 stops
Air Canada Logo
10:55 am - 9:00 am
GCM
-
ORD
22h 05m
1 stop
$413Air Canada
Sat, Jun 6 - Sat, Jun 13

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 14
ORD12:44 amChicago O'Hare Intl
5h 00m
SJU6:44 amSan Juan Luis Munoz Marin Intl
Aug 22
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 25m
1 stop
ORD12:25 pmChicago O'Hare Intl
$228
Frontier
Sep 5
ORD12:29 amChicago O'Hare Intl
4h 57m
SJU6:26 amSan Juan Luis Munoz Marin Intl
Sep 10
SJU5:12 pmSan Juan Luis Munoz Marin Intl
23h 14m
1 stop
ORD3:26 pmChicago O'Hare Intl
$229
Frontier
Aug 15
ORD12:44 amChicago O'Hare Intl
5h 00m
SJU6:44 amSan Juan Luis Munoz Marin Intl
Aug 22
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 25m
1 stop
ORD12:25 pmChicago O'Hare Intl
$230

Delta flights from Chicago O'Hare Intl Airport to Caribbean

Our best Delta deals on Chicago O'Hare Intl Airport to Caribbean flight tickets
Delta
Aug 19
ORD6:40 amChicago O'Hare Intl
8h 57m
1 stop
SJU4:37 pmSan Juan Luis Munoz Marin Intl
Sep 2
SJU5:45 pmSan Juan Luis Munoz Marin Intl
7h 12m
1 stop
ORD11:57 pmChicago O'Hare Intl
$226
Delta
Aug 22
ORD1:48 pmChicago O'Hare Intl
7h 41m
1 stop
SJU10:29 pmSan Juan Luis Munoz Marin Intl
Aug 27
SJU5:49 pmSan Juan Luis Munoz Marin Intl
7h 09m
1 stop
ORD11:58 pmChicago O'Hare Intl
$236
Delta
Aug 15
ORD10:50 amChicago O'Hare Intl
10h 39m
1 stop
SJU10:29 pmSan Juan Luis Munoz Marin Intl
Aug 29
SJU5:49 pmSan Juan Luis Munoz Marin Intl
7h 09m
1 stop
ORD11:58 pmChicago O'Hare Intl
$246

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 May 12, 2026.
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

Cheapest round-trip

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/23

5:14 pm-11:07 pm

Nonstop4h 53m

San Juan Luis Munoz Marin Intl

Wed 8/26

7:14 pm-9:00 am

1 stop14h 46m

$222

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 8/19

6:40 am-4:37 pm

1 stop8h 57m

San Juan Luis Munoz Marin Intl

Wed 9/2

5:45 pm-11:57 pm

1 stop7h 12m

$226

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 8/14

12:44 am-6:44 am

Nonstop5h 00m

San Juan Luis Munoz Marin Intl

Sat 8/22

6:00 am-12:25 pm

1 stop7h 25m

$228

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 9/5

12:29 am-6:26 am

Nonstop4h 57m

San Juan Luis Munoz Marin Intl

Thu 9/10

5:12 pm-3:26 pm

1 stop23h 14m

$229

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Tue 8/11

7:00 am-1:48 pm

1 stop5h 48m

Nassau Intl

Thu 8/20

3:02 pm-11:44 pm

1 stop9h 42m

$284

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Sat 8/8

7:00 am-5:14 pm

1 stop9h 14m

Nassau Intl

Wed 8/19

3:02 pm-11:44 pm

1 stop9h 42m

$303
Quickest round-trip

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 8/22

12:12 pm-5:57 pm

Nonstop4h 45m

Punta Cana

Sat 8/29

7:02 am-11:12 am

Nonstop5h 10m

$366

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 11/6

5:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Sun 11/15

6:10 pm-9:20 pm

Nonstop5h 10m

$371

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 6/5

8:20 pm-10:00 am

1 stop13h 40m

George Town Owen Roberts Intl

Sat 6/13

10:55 am-9:00 am

1 stop22h 05m

$403

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 6/6

6:22 pm-11:25 am

2 stops41h 03m

George Town Owen Roberts Intl

Sat 6/13

10:55 am-9:00 am

1 stop22h 05m

$413

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, July 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 $397. If you don’t want to visit Caribbean in July, then you should wait until October to fly from Chicago O'Hare Intl Airport, when ticket prices are also cheap, with an average price of $431.

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 $382. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $465. 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 $374. Flying to Caribbean in the evening is an ideal time because this is during off-peak travel hours. Flights at noon are often more expensive with an average ticket price of $484.

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 from Chicago O'Hare Intl Airport 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 $385 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 $347 on momondo.

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

You could potentially save up to 1% 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

$135

Fastest flight time

3h 25m

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 $135. The best round-trip flight deal from Chicago O'Hare Intl Airport to Caribbean found on momondo in the last 72 hours is $306.
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 195 airports in Caribbean. From Chicago O'Hare Intl Airport there are direct flights to Nassau Intl (NAS), Montego Bay Sangster Intl (MBJ).
Search flight deals

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Caribbean

  • 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
Spirit AirlinesPriceFrom $100Free CancellationRating
6.3
8,633 reviews
Search Spirit Airlines flights
JetBluePriceFrom $119Free CancellationRating
7.1
2,972 reviews
Search JetBlue flights
FrontierPriceFrom $122Free CancellationRating
5.6
2,952 reviews
Search Frontier flights
DeltaPriceFrom $143Free CancellationRating
7.9
8,450 reviews
Search Delta flights
Air CanadaPriceFrom $175Free CancellationRating
7.1
11,025 reviews
Search Air Canada flights
Hahn AirPriceFrom $213Free CancellationRating
0.0
Search Hahn Air flights
ArajetPriceFrom $215Free CancellationRating
6.5
48 reviews
Search Arajet flights
United AirlinesPriceFrom $256Free CancellationRating
7.4
9,704 reviews
Search United Airlines flights
American AirlinesPriceFrom $309Free CancellationRating
7.1
11,665 reviews
Search American Airlines 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

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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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