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Cheap flights from Chicago O'Hare Intl Airport to Caribbean from $59

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 2/28. 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.
Spirit Airlines Logo
7:23 pm - 6:58 pm
ORD
-
SJU
21h 35m
1 stop
Spirit Airlines Logo
11:52 am - 6:18 pm
SJU
-
ORD
8h 26m
1 stop
$184Spirit Airlines
Sun, Mar 1 - Fri, Mar 6
Spirit Airlines Logo
10:55 am - 11:58 pm
ORD
-
SJU
12h 03m
1 stop
Spirit Airlines Logo
12:55 pm - 7:51 pm
SJU
-
ORD
7h 56m
1 stop
$185Spirit Airlines
Mon, Mar 16 - Wed, Mar 18
Multiple Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Multiple Airlines Logo
5:25 pm - 10:46 am
SJU
-
ORD
19h 21m
1 stop
$186Multiple Airlines
Sat, Feb 14 - Wed, Feb 18
Multiple Airlines Logo
8:30 am - 12:43 am
ORD
-
SJU
14h 13m
1 stop
Multiple Airlines Logo
3:36 pm - 11:47 pm
SJU
-
ORD
9h 11m
1 stop
$187Multiple Airlines
Wed, Mar 4 - Tue, Mar 10
Frontier Logo
8:15 am - 2:53 am
ORD
-
SJU
16h 38m
1 stop
Frontier Logo
5:25 pm - 10:46 am
SJU
-
ORD
19h 21m
1 stop
$188Frontier
Sat, Feb 21 - Wed, Feb 25
Arajet Logo
5:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
7:30 pm - 10:40 pm
PUJ
-
ORD
5h 10mnonstop
$283Arajet
Mon, Feb 16 - Tue, Feb 17
Frontier Logo
7:30 am - 2:13 pm
ORD
-
PUJ
4h 43mnonstop
Frontier Logo
5:39 pm - 10:04 pm
PUJ
-
ORD
5h 25mnonstop
$291Frontier
Fri, Mar 6 - Mon, Mar 9
JetBlue Logo
6:20 pm - 11:10 am
ORD
-
AUA
15h 50m
1 stop
JetBlue Logo
5:15 pm - 9:10 am
AUA
-
ORD
16h 55m
1 stop
$331JetBlue
Mon, Mar 30 - Mon, Apr 6
American Airlines Logo
8:20 am - 1:26 pm
ORD
-
MBJ
4h 06mnonstop
American Airlines Logo
10:07 am - 6:28 pm
MBJ
-
ORD
8h 21m
1 stop
$367American Airlines
Tue, Mar 3 - Tue, Mar 10
JetBlue Logo
10:00 am - 2:57 pm
ORD
-
CUR
26h 57m
2 stops
JetBlue Logo
3:54 pm - 9:10 am
CUR
-
ORD
19h 16m
2 stops
$416JetBlue
Wed, Feb 18 - Wed, Feb 25

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
Mar 1
ORD7:23 pmChicago O'Hare Intl
21h 35m
1 stop
SJU6:58 pmSan Juan Luis Munoz Marin Intl
Mar 6
SJU11:52 amSan Juan Luis Munoz Marin Intl
8h 26m
1 stop
ORD6:18 pmChicago O'Hare Intl
$184
Spirit Airlines
Mar 16
ORD10:55 amChicago O'Hare Intl
12h 03m
1 stop
SJU11:58 pmSan Juan Luis Munoz Marin Intl
Mar 18
SJU12:55 pmSan Juan Luis Munoz Marin Intl
7h 56m
1 stop
ORD7:51 pmChicago O'Hare Intl
$185
Spirit Airlines
Feb 9
ORD12:17 pmChicago O'Hare Intl
4h 32m
SJU6:49 pmSan Juan Luis Munoz Marin Intl
Feb 14
SJU12:32 pmSan Juan Luis Munoz Marin Intl
5h 16m
ORD3:48 pmChicago O'Hare Intl
$188

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
Feb 21
ORD8:15 amChicago O'Hare Intl
16h 38m
1 stop
SJU2:53 amSan Juan Luis Munoz Marin Intl
Feb 25
SJU5:25 pmSan Juan Luis Munoz Marin Intl
19h 21m
1 stop
ORD10:46 amChicago O'Hare Intl
$188
Frontier
Mar 4
ORD8:30 amChicago O'Hare Intl
16h 23m
1 stop
SJU2:53 amSan Juan Luis Munoz Marin Intl
Mar 8
SJU3:08 amSan Juan Luis Munoz Marin Intl
21h 30m
1 stop
ORD11:38 pmChicago O'Hare Intl
$197
Frontier
Apr 23
ORD12:25 pmChicago O'Hare Intl
9h 15m
1 stop
SJU10:40 pmSan Juan Luis Munoz Marin Intl
Apr 27
SJU10:55 amSan Juan Luis Munoz Marin Intl
10h 13m
1 stop
ORD8:08 pmChicago O'Hare Intl
$202

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 February 3, 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

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 3/1

7:23 pm-6:58 pm

1 stop21h 35m

San Juan Luis Munoz Marin Intl

Fri 3/6

11:52 am-6:18 pm

1 stop8h 26m

$184

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/16

10:55 am-11:58 pm

1 stop12h 03m

San Juan Luis Munoz Marin Intl

Wed 3/18

12:55 pm-7:51 pm

1 stop7h 56m

$185

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/14

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Wed 2/18

5:25 pm-10:46 am

1 stop19h 21m

$186

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 3/4

8:30 am-12:43 am

1 stop14h 13m

San Juan Luis Munoz Marin Intl

Tue 3/10

3:36 pm-11:47 pm

1 stop9h 11m

$187

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

8:15 am-2:53 am

1 stop16h 38m

San Juan Luis Munoz Marin Intl

Wed 2/25

5:25 pm-10:46 am

1 stop19h 21m

$188

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 2/16

5:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Tue 2/17

7:30 pm-10:40 pm

Nonstop5h 10m

$283

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 3/6

7:30 am-2:13 pm

Nonstop4h 43m

Punta Cana

Mon 3/9

5:39 pm-10:04 pm

Nonstop5h 25m

$291

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

Mon 3/30

6:20 pm-11:10 am

1 stop15h 50m

Oranjestad Reina Beatrix

Mon 4/6

5:15 pm-9:10 am

1 stop16h 55m

$331

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 3/3

8:20 am-1:26 pm

Nonstop4h 06m

Montego Bay Sangster Intl

Tue 3/10

10:07 am-6:28 pm

1 stop8h 21m

$367

ChicagoWillemstad

ORD - CUR

ORDCUR

Chicago O'Hare Intl

Wed 2/18

10:00 am-2:57 pm

2 stops26h 57m

Willemstad Hato Int.

Wed 2/25

3:54 pm-9:10 am

2 stops19h 16m

$416

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, 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 $340. 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 $382. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $448. 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 $332. 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 $478.

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 $391 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 $329 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

$128

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 $128. The best round-trip flight deal from Chicago O'Hare Intl Airport to Caribbean found on momondo in the last 72 hours is $296.
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 George Town Owen Roberts Intl (GCM), Nassau Intl (NAS).
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
5.7
3,051 reviews
Search Frontier flights
JetBluePriceFrom $119Free CancellationRating
7.2
2,893 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $130Free CancellationRating
6.3
8,408 reviews
Search Spirit Airlines flights
DeltaPriceFrom $136Free CancellationRating
7.9
8,139 reviews
Search Delta flights
Air CanadaPriceFrom $175Free CancellationRating
7.1
10,685 reviews
Search Air Canada flights
ArajetPriceFrom $181Free CancellationRating
6.6
43 reviews
Search Arajet flights
Copa AirlinesPriceFrom $188Free CancellationRating
7.6
1,558 reviews
Search Copa Airlines flights
Hahn AirPriceFrom $213Free CancellationRating
0.0
Search Hahn Air flights
AviancaPriceFrom $250Free CancellationRating
6.5
2,498 reviews
Search Avianca 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.

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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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