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Cheap flights from Chicago O'Hare Intl Airport to Caribbean Islands from $98

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 9/20. 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

Frontier Logo
6:40 am - 3:24 pmORD-SJU
7h 44m1 stop
Frontier Logo
3:40 am - 3:39 pmSJU-ORD
12h 59m1 stop
$216Frontier
Find Deal
Sat, Oct 11 - Fri, Oct 17
Spirit Airlines Logo
5:05 am - 9:48 pmORD-SJU
15h 43m1 stop
Spirit Airlines Logo
7:40 pm - 11:56 pmSJU-ORD
5h 16mnonstop
$220Spirit Airlines
Find Deal
Sun, Aug 31 - Fri, Sep 5
Arajet Logo
4:35 am - 11:20 amORD-PUJ
4h 45mnonstop
Arajet Logo
6:00 pm - 9:10 pmPUJ-ORD
5h 10mnonstop
$303Arajet
Find Deal
Tue, Dec 9 - Sun, Dec 14
Arajet Logo
10:27 am - 5:12 pmORD-PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 8:57 amPUJ-ORD
5h 10mnonstop
$308Arajet
Find Deal
Sat, Dec 6 - Sat, Dec 13
American Airlines Logo
8:35 am - 2:05 pmORD-PUJ
4h 30mnonstop
American Airlines Logo
3:21 pm - 7:36 pmPUJ-ORD
5h 15mnonstop
$338American Airlines
Find Deal
Mon, Oct 13 - Wed, Oct 22
American Airlines Logo
5:20 am - 3:29 pmORD-PUJ
9h 09m1 stop
American Airlines Logo
3:21 pm - 7:36 pmPUJ-ORD
5h 15mnonstop
$342American Airlines
Find Deal
Tue, Oct 7 - Fri, Oct 10
Delta Logo
7:59 pm - 2:31 pmORD-PUJ
17h 32m1 stop
Delta Logo
2:49 pm - 11:57 pmPUJ-ORD
10h 08m1 stop
$343Delta
Find Deal
Sun, Oct 26 - Wed, Oct 29
Delta Logo
5:20 am - 1:24 pmORD-PUJ
7h 04m1 stop
Delta Logo
1:53 pm - 7:50 amPUJ-ORD
18h 57m2 stops
$347Delta
Find Deal
Mon, Oct 27 - Tue, Oct 28
United Airlines Logo
6:20 pm - 11:50 amORD-NAS
16h 30m1 stop
United Airlines Logo
2:55 pm - 9:07 pmNAS-ORD
7h 12m1 stop
$474United Airlines
Find Deal
Fri, Nov 28 - Thu, Dec 4
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

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
Aug 31
ORD5:05 amChicago O'Hare Intl
15h 43m
1 stop
SJU9:48 pmSan Juan Luis Munoz Marin Intl
Sep 5
SJU7:40 pmSan Juan Luis Munoz Marin Intl
5h 16m
ORD11:56 pmChicago O'Hare Intl
$220
Find similar
Spirit Airlines
Aug 31
ORD5:05 amChicago O'Hare Intl
15h 43m
1 stop
SJU9:48 pmSan Juan Luis Munoz Marin Intl
Sep 5
SJU3:19 pmSan Juan Luis Munoz Marin Intl
7h 39m
1 stop
ORD9:58 pmChicago O'Hare Intl
$226
Find similar
Spirit Airlines
Aug 25
ORD5:05 amChicago O'Hare Intl
15h 43m
1 stop
SJU9:48 pmSan Juan Luis Munoz Marin Intl
Sep 25
SJU7:40 pmSan Juan Luis Munoz Marin Intl
5h 16m
ORD11:56 pmChicago O'Hare Intl
$230
Find similar

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
Oct 11
ORD6:40 amChicago O'Hare Intl
7h 44m
1 stop
SJU3:24 pmSan Juan Luis Munoz Marin Intl
Oct 17
SJU3:40 amSan Juan Luis Munoz Marin Intl
12h 59m
1 stop
ORD3:39 pmChicago O'Hare Intl
$216
Find similar
Frontier
Oct 18
ORD2:45 pmChicago O'Hare Intl
9h 00m
1 stop
SJU12:45 amSan Juan Luis Munoz Marin Intl
Oct 21
SJU1:17 pmSan Juan Luis Munoz Marin Intl
26h 51m
1 stop
ORD3:08 pmChicago O'Hare Intl
$238
Find similar
Frontier
Sep 6
ORD8:00 amChicago O'Hare Intl
14h 59m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
Sep 12
SJU7:15 amSan Juan Luis Munoz Marin Intl
9h 35m
1 stop
ORD3:50 pmChicago O'Hare Intl
$258
Find similar

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 August 20, 2025.
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

Sat 10/11

6:40 am-3:24 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

Fri 10/17

3:40 am-3:39 pm

1 stop12h 59m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/31

5:05 am-9:48 pm

1 stop15h 43m

San Juan Luis Munoz Marin Intl

Fri 9/5

7:40 pm-11:56 pm

Nonstop5h 16m

$220

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 12/9

4:35 am-11:20 am

Nonstop4h 45m

Punta Cana

Sun 12/14

6:00 pm-9:10 pm

Nonstop5h 10m

$303

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 12/6

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 12/13

5:47 am-8:57 am

Nonstop5h 10m

$308

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 10/13

8:35 am-2:05 pm

Nonstop4h 30m

Punta Cana

Wed 10/22

3:21 pm-7:36 pm

Nonstop5h 15m

$338

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 10/7

5:20 am-3:29 pm

1 stop9h 09m

Punta Cana

Fri 10/10

3:21 pm-7:36 pm

Nonstop5h 15m

$342

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 10/26

7:59 pm-2:31 pm

1 stop17h 32m

Punta Cana

Wed 10/29

2:49 pm-11:57 pm

1 stop10h 08m

$343

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 10/27

5:20 am-1:24 pm

1 stop7h 04m

Punta Cana

Tue 10/28

1:53 pm-7:50 am

2 stops18h 57m

$347

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Fri 11/28

6:20 pm-11:50 am

1 stop16h 30m

Nassau Intl

Thu 12/4

2:55 pm-9:07 pm

1 stop7h 12m

$474

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

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 $340. The month of January is another great option to travel to Caribbean Islands, with average flight prices from Chicago O'Hare Intl Airport averaging around $345.

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 $392. If your travel schedule is flexible, try to avoid departing on a Sunday 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 $306. 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 in the morning because they tend to be around $444. 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 $383 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 $306 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 18m

Direct flights

Every day

Airports in Caribbean Islands

4 airports
The fastest flight from Chicago O'Hare Intl Airport to Caribbean Islands takes 3h 18m
Direct flights go from Chicago O'Hare Intl Airport to Caribbean Islands every day.
There are 4 airports near Caribbean Islands: George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Montego Bay Sangster Intl (MBJ), Providenciales (PLS)
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
5.8
3,207 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,039 reviews
Search Spirit Airlines flights
DeltaPriceFrom $190Free CancellationRating
7.9
7,982 reviews
Search Delta flights
Copa AirlinesPriceFrom $193Free CancellationRating
7.5
1,510 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,928 reviews
Search United Airlines flights
ArajetPriceFrom $234Free CancellationRating
7.0
34 reviews
Search Arajet flights
JetBluePriceFrom $261Free CancellationRating
7.2
2,916 reviews
Search JetBlue flights
Air CanadaPriceFrom $335Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
American AirlinesPriceFrom $346Free CancellationRating
7.2
10,000 reviews
Search American 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.

An easier way to manage your Caribbean Islands trip

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