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

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 2/6. 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
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Spirit Airlines Logo
4:40 pm - 11:46 pm
SJU
-
ORD
9h 06m
1 stop
$189Spirit Airlines
Thu, Jan 22 - Wed, Jan 28
Spirit Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Spirit Airlines Logo
11:52 am - 6:18 pm
SJU
-
ORD
8h 26m
1 stop
$190Spirit Airlines
Mon, Feb 23 - Thu, Feb 26
Multiple Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Multiple Airlines Logo
8:00 am - 10:41 am
SJU
-
ORD
28h 41m
1 stop
$191Multiple Airlines
Sat, Jan 24 - Sun, Feb 1
Spirit Airlines Logo
9:23 am - 6:58 pm
ORD
-
SJU
7h 35m
1 stop
Spirit Airlines Logo
12:32 pm - 3:48 pm
SJU
-
ORD
5h 16mnonstop
$192Spirit Airlines
Mon, Feb 2 - Thu, Feb 12
Frontier Logo
6:03 am - 5:00 pm
ORD
-
SJU
8h 57m
1 stop
Frontier Logo
12:55 pm - 9:27 pm
SJU
-
ORD
10h 32m
1 stop
$195Frontier
Sat, Jan 24 - Mon, Jan 26
Arajet Logo
11:27 am - 6:12 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
7:17 am - 10:27 am
PUJ
-
ORD
5h 10mnonstop
$259Arajet
Sat, Jan 24 - Sat, Jan 31
Arajet Logo
10:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
$267Arajet
Sat, Feb 7 - Sat, Feb 14
Frontier Logo
8:59 pm - 2:46 pm
ORD
-
MBJ
17h 47m
2 stops
Frontier Logo
4:06 pm - 12:01 am
MBJ
-
ORD
7h 55m
1 stop
$392Frontier
Fri, Apr 3 - Mon, Apr 6
Delta Logo
5:30 am - 12:54 pm
ORD
-
MBJ
6h 24m
1 stop
Delta Logo
4:45 pm - 11:56 pm
MBJ
-
ORD
8h 11m
1 stop
$396Delta
Sun, Feb 8 - Wed, Feb 11
American Airlines Logo
9:10 pm - 11:33 am
ORD
-
MBJ
13h 23m
2 stops
American Airlines Logo
1:58 pm - 11:27 pm
MBJ
-
ORD
10h 29m
2 stops
$401American Airlines
Tue, Feb 3 - Wed, Feb 11

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
Jan 24
ORD6:03 amChicago O'Hare Intl
8h 57m
1 stop
SJU5:00 pmSan Juan Luis Munoz Marin Intl
Jan 26
SJU12:55 pmSan Juan Luis Munoz Marin Intl
10h 32m
1 stop
ORD9:27 pmChicago O'Hare Intl
$195
Frontier
Jan 22
ORD11:51 amChicago O'Hare Intl
10h 08m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
Jan 28
SJU4:36 pmSan Juan Luis Munoz Marin Intl
20h 05m
1 stop
ORD10:41 amChicago O'Hare Intl
$196
Frontier
Feb 7
ORD6:03 amChicago O'Hare Intl
8h 57m
1 stop
SJU5:00 pmSan Juan Luis Munoz Marin Intl
Feb 14
SJU7:54 pmSan Juan Luis Munoz Marin Intl
27h 03m
1 stop
ORD8:57 pmChicago O'Hare Intl
$203

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 20
ORD6:05 amChicago O'Hare Intl
15h 28m
1 stop
SJU11:33 pmSan Juan Luis Munoz Marin Intl
Jan 22
SJU1:22 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD4:37 pmChicago O'Hare Intl
$192
Spirit Airlines
Feb 7
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
$193
Spirit Airlines
Jan 18
ORD8:43 pmChicago O'Hare Intl
16h 52m
1 stop
SJU3:35 pmSan Juan Luis Munoz Marin Intl
Jan 27
SJU6:00 amSan Juan Luis Munoz Marin Intl
9h 13m
1 stop
ORD1:13 pmChicago O'Hare Intl
$194

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 January 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

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 1/22

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Wed 1/28

4:40 pm-11:46 pm

1 stop9h 06m

$189

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 2/23

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Thu 2/26

11:52 am-6:18 pm

1 stop8h 26m

$190

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

Sun 2/1

8:00 am-10:41 am

1 stop28h 41m

$191

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 2/2

9:23 am-6:58 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Thu 2/12

12:32 pm-3:48 pm

Nonstop5h 16m

$192

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

6:03 am-5:00 pm

1 stop8h 57m

San Juan Luis Munoz Marin Intl

Mon 1/26

12:55 pm-9:27 pm

1 stop10h 32m

$195

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 1/24

11:27 am-6:12 pm

Nonstop4h 45m

Punta Cana

Sat 1/31

7:17 am-10:27 am

Nonstop5h 10m

$259

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 2/7

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 2/14

5:47 am-8:57 am

Nonstop5h 10m

$267

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 4/3

8:59 pm-2:46 pm

2 stops17h 47m

Montego Bay Sangster Intl

Mon 4/6

4:06 pm-12:01 am

1 stop7h 55m

$392

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 2/8

5:30 am-12:54 pm

1 stop6h 24m

Montego Bay Sangster Intl

Wed 2/11

4:45 pm-11:56 pm

1 stop8h 11m

$396

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/3

9:10 pm-11:33 am

2 stops13h 23m

Montego Bay Sangster Intl

Wed 2/11

1:58 pm-11:27 pm

2 stops10h 29m

$401

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 $342. If you don’t want to visit Caribbean in April, 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 $349.

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 $385. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $447. 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 $327. 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 $441.

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 $394 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.

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

$133

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 $133. The best round-trip flight deal from Chicago O'Hare Intl Airport to Caribbean found on momondo in the last 72 hours is $312.
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).
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 $113Free CancellationRating
5.7
3,056 reviews
Search Frontier flights
JetBluePriceFrom $120Free CancellationRating
7.2
2,884 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $152Free CancellationRating
6.3
8,303 reviews
Search Spirit Airlines flights
DeltaPriceFrom $186Free CancellationRating
7.9
8,039 reviews
Search Delta flights
Copa AirlinesPriceFrom $188Free CancellationRating
7.6
1,558 reviews
Search Copa Airlines flights
ArajetPriceFrom $199Free CancellationRating
6.4
41 reviews
Search Arajet flights
United AirlinesPriceFrom $267Free CancellationRating
7.4
9,149 reviews
Search United Airlines flights
SouthwestPriceFrom $277Free CancellationRating
8.0
4,256 reviews
Search Southwest flights
American AirlinesPriceFrom $344Free CancellationRating
7.2
11,114 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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