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Cheap flights from Chicago O'Hare Intl Airport to Caribbean Islands from $72

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 Islands 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 Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
12:18 pm - 5:54 pm
ORD
-
SJU
4h 36mnonstop
Spirit Airlines Logo
12:30 pm - 4:38 pm
SJU
-
ORD
5h 08mnonstop
$179Spirit Airlines
Mon, Apr 20 - Thu, Apr 23
Spirit Airlines Logo
5:15 am - 3:31 pm
ORD
-
SJU
8h 16m
1 stop
Spirit Airlines Logo
11:52 am - 6:18 pm
SJU
-
ORD
8h 26m
1 stop
$181Spirit Airlines
Sun, Mar 1 - Thu, Mar 5
Spirit Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Spirit Airlines Logo
4:36 pm - 11:47 pm
SJU
-
ORD
9h 11m
1 stop
$182Spirit Airlines
Mon, Feb 23 - Thu, Feb 26
Frontier Logo
1:27 pm - 12:33 pm
ORD
-
SJU
22h 06m
1 stop
Frontier Logo
6:00 am - 10:57 pm
SJU
-
ORD
17h 57m
1 stop
$184Frontier
Sat, May 9 - Fri, May 15
Arajet Logo
6:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 9:57 am
PUJ
-
ORD
5h 10mnonstop
$278Arajet
Mon, Mar 9 - Sat, Mar 14
Arajet Logo
10:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
$284Arajet
Sat, Feb 28 - Sat, Mar 7
American Airlines Logo
7:15 am - 1:25 pm
ORD
-
MBJ
6h 10m
1 stop
American Airlines Logo
4:37 pm - 12:11 pm
MBJ
-
ORD
19h 34m
1 stop
$365American Airlines
Thu, Apr 16 - Mon, Apr 20
American Airlines Logo
6:05 am - 1:25 pm
ORD
-
MBJ
7h 20m
1 stop
American Airlines Logo
4:37 pm - 12:25 am
MBJ
-
ORD
7h 48m
1 stop
$366American Airlines
Thu, Apr 16 - Wed, Apr 22
Delta Logo
7:14 pm - 3:28 pm
ORD
-
MBJ
20h 14m
2 stops
Delta Logo
4:32 pm - 10:09 am
MBJ
-
ORD
17h 37m
2 stops
$367Delta
Tue, Apr 7 - Thu, Apr 23
Delta Logo
7:59 pm - 10:00 am
ORD
-
MBJ
14h 01m
1 stop
Delta Logo
2:25 pm - 9:25 am
MBJ
-
ORD
19h 00m
1 stop
$368Delta
Sun, Mar 29 - Sun, Apr 5

Spirit Airlines flights from Chicago O'Hare Intl Airport to Caribbean Islands

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Caribbean Islands flight tickets
Spirit Airlines
Apr 20
ORD12:18 pmChicago O'Hare Intl
4h 36m
SJU5:54 pmSan Juan Luis Munoz Marin Intl
Apr 23
SJU12:30 pmSan Juan Luis Munoz Marin Intl
5h 08m
ORD4:38 pmChicago O'Hare Intl
$179
Spirit Airlines
Mar 1
ORD5:15 amChicago O'Hare Intl
8h 16m
1 stop
SJU3:31 pmSan Juan Luis Munoz Marin Intl
Mar 5
SJU11:52 amSan Juan Luis Munoz Marin Intl
8h 26m
1 stop
ORD6:18 pmChicago O'Hare Intl
$181
Spirit Airlines
Feb 22
ORD12:17 pmChicago O'Hare Intl
4h 32m
SJU6:49 pmSan Juan Luis Munoz Marin Intl
Feb 26
SJU11:52 amSan Juan Luis Munoz Marin Intl
8h 26m
1 stop
ORD6:18 pmChicago O'Hare Intl
$182

Frontier flights from Chicago O'Hare Intl Airport to Caribbean Islands

Our best Frontier deals on Chicago O'Hare Intl Airport to Caribbean Islands flight tickets
Frontier
May 9
ORD1:27 pmChicago O'Hare Intl
22h 06m
1 stop
SJU12:33 pmSan Juan Luis Munoz Marin Intl
May 15
SJU6:00 amSan Juan Luis Munoz Marin Intl
17h 57m
1 stop
ORD10:57 pmChicago O'Hare Intl
$184
Frontier
Mar 4
ORD8:30 amChicago O'Hare Intl
16h 23m
1 stop
SJU2:53 amSan Juan Luis Munoz Marin Intl
Mar 11
SJU6:30 amSan Juan Luis Munoz Marin Intl
18h 08m
1 stop
ORD11:38 pmChicago O'Hare Intl
$199
Frontier
May 11
ORD1:12 pmChicago O'Hare Intl
10h 28m
1 stop
SJU12:40 amSan Juan Luis Munoz Marin Intl
May 15
SJU4:11 pmSan Juan Luis Munoz Marin Intl
8h 05m
1 stop
ORD11:16 pmChicago O'Hare Intl
$202

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to Caribbean Islands 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 13, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 4/20

12:18 pm-5:54 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

Thu 4/23

12:30 pm-4:38 pm

Nonstop5h 08m

$179

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 3/1

5:15 am-3:31 pm

1 stop8h 16m

San Juan Luis Munoz Marin Intl

Thu 3/5

11:52 am-6:18 pm

1 stop8h 26m

$181

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

4:36 pm-11:47 pm

1 stop9h 11m

$182

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/9

1:27 pm-12:33 pm

1 stop22h 06m

San Juan Luis Munoz Marin Intl

Fri 5/15

6:00 am-10:57 pm

1 stop17h 57m

$184

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 3/9

6:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Sat 3/14

5:47 am-9:57 am

Nonstop5h 10m

$278

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 2/28

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 3/7

5:47 am-8:57 am

Nonstop5h 10m

$284

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 4/16

7:15 am-1:25 pm

1 stop6h 10m

Montego Bay Sangster Intl

Mon 4/20

4:37 pm-12:11 pm

1 stop19h 34m

$365

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 4/16

6:05 am-1:25 pm

1 stop7h 20m

Montego Bay Sangster Intl

Wed 4/22

4:37 pm-12:25 am

1 stop7h 48m

$366

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 4/7

7:14 pm-3:28 pm

2 stops20h 14m

Montego Bay Sangster Intl

Thu 4/23

4:32 pm-10:09 am

2 stops17h 37m

$367

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 3/29

7:59 pm-10:00 am

1 stop14h 01m

Montego Bay Sangster Intl

Sun 4/5

2:25 pm-9:25 am

1 stop19h 00m

$368

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Caribbean Islands

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 Islands?

The month of September is, on average, the cheapest month to fly to Caribbean Islands from Chicago O'Hare Intl Airport, with most prices found around $321. The month of April is another great option to travel to Caribbean Islands, with average flight prices from Chicago O'Hare Intl Airport averaging around $332.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Chicago O'Hare Intl Airport to Caribbean Islands is on a Monday. Travelers who choose to depart for Caribbean Islands on a Monday will often find tickets for as low as $381. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $446. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Chicago O'Hare Intl Airport to Caribbean Islands in the evening for as low as $326. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets at noon because they tend to be around $479. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago O'Hare Intl - Caribbean Islands flight prices

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands 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 Islands from Chicago O'Hare Intl Airport for as low as $328 on momondo.

What cabin class options are available on Chicago O'Hare Intl to Caribbean Islands flights?

There are 4 cabin classes available to choose from on Chicago O'Hare Intl to Caribbean Islands 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 Islands flights?

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

Cheap Chicago O'Hare Intl Airport to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Caribbean Islands

Fastest flight time

3h 24m

Direct flights

Every day

Airports in Caribbean Islands

99 airports
The fastest flight from Chicago O'Hare Intl Airport to Caribbean Islands takes 3h 24m
Direct flights go from Chicago O'Hare Intl Airport to Caribbean Islands every day.
There are 99 airports in Caribbean Islands. From Chicago O'Hare Intl Airport there are direct flights to Nassau Intl (NAS).
Search flight deals

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Caribbean Islands?

    Prices for flights from Chicago O'Hare Intl Airport to Caribbean Islands are updated daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Caribbean Islands?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Caribbean Islands?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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 Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago O'Hare Intl Airport to Caribbean Islands?

Best airlines flying from Chicago O'Hare Intl Airport to Caribbean Islands

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $106Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
JetBluePriceFrom $119Free CancellationRating
7.2
2,897 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $130Free CancellationRating
6.3
8,450 reviews
Search Spirit Airlines flights
DeltaPriceFrom $136Free CancellationRating
7.9
8,196 reviews
Search Delta flights
ArajetPriceFrom $180Free CancellationRating
6.6
43 reviews
Search Arajet flights
Copa AirlinesPriceFrom $188Free CancellationRating
7.5
1,559 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $193Free CancellationRating
7.1
10,717 reviews
Search Air Canada flights
Hahn AirPriceFrom $213Free CancellationRating
0.0
Search Hahn Air flights
United AirlinesPriceFrom $251Free CancellationRating
7.4
9,286 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Caribbean Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Caribbean Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Caribbean Islands with flexible booking policies on momondo?

All flight searches from Chicago to Caribbean Islands on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Caribbean Islands?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Caribbean Islands from Chicago.

I’m not ready to book a flight from Chicago to Caribbean Islands right now. Can momondo alert me if prices change?

Price alerts on flights to Caribbean Islands from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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