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Cheap flights from Chicago O'Hare Intl Airport to Caribbean Islands from $97

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 4/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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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.
Multiple Airlines Logo
12:33 am - 6:24 am
ORD
-
SJU
4h 51mnonstop
Multiple Airlines Logo
11:39 am - 3:49 pm
SJU
-
ORD
5h 10mnonstop
$214Multiple Airlines
Sun, May 31 - Thu, Jun 4
Frontier Logo
5:30 pm - 8:04 am
ORD
-
SJU
13h 34m
1 stop
Frontier Logo
6:11 pm - 10:26 pm
SJU
-
ORD
5h 15mnonstop
$215Frontier
Sat, Jun 6 - Fri, Jun 12
Multiple Airlines Logo
4:44 pm - 10:21 pm
ORD
-
SJU
4h 37mnonstop
Multiple Airlines Logo
6:00 am - 12:37 pm
SJU
-
ORD
7h 37m
1 stop
$216Multiple Airlines
Fri, May 22 - Fri, May 29
Spirit Airlines Logo
10:00 am - 3:39 pm
ORD
-
SJU
4h 39mnonstop
Spirit Airlines Logo
12:57 pm - 12:24 am
SJU
-
ORD
12h 27m
1 stop
$219Spirit Airlines
Sun, Apr 19 - Wed, Apr 22
Spirit Airlines Logo
7:17 am - 3:28 pm
ORD
-
STT
7h 11m
1 stop
Spirit Airlines Logo
5:10 pm - 12:24 am
STT
-
ORD
8h 14m
1 stop
$259Spirit Airlines
Mon, Apr 13 - Fri, Apr 17
Arajet Logo
12:12 pm - 5:57 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
$299Arajet
Sat, Aug 1 - Sat, Aug 8
American Airlines Logo
8:05 am - 12:13 pm
ORD
-
MBJ
4h 08mnonstop
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
$318American Airlines
Tue, Apr 14 - Wed, Apr 22
American Airlines Logo
7:22 am - 1:19 pm
ORD
-
MBJ
5h 57m
1 stop
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
$322American Airlines
Tue, Apr 14 - Wed, Apr 22
Air Canada Logo
6:04 pm - 11:25 am
ORD
-
GCM
41h 21m
2 stops
Air Canada Logo
12:25 pm - 4:57 pm
GCM
-
ORD
28h 32m
1 stop
$338Air Canada
Sat, Jun 20 - Thu, Jun 25
Air Canada Logo
9:55 am - 10:00 am
ORD
-
GCM
24h 05m
1 stop
Air Canada Logo
12:25 pm - 9:05 am
GCM
-
ORD
20h 40m
1 stop
$345Air Canada
Fri, Jun 5 - Mon, Jun 8

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 11
ORD5:05 amChicago O'Hare Intl
12h 50m
1 stop
SJU6:55 pmSan Juan Luis Munoz Marin Intl
Apr 18
SJU7:00 amSan Juan Luis Munoz Marin Intl
8h 05m
1 stop
ORD2:05 pmChicago O'Hare Intl
$212
Spirit Airlines
Apr 6
ORD6:10 pmChicago O'Hare Intl
16h 39m
1 stop
SJU11:49 amSan Juan Luis Munoz Marin Intl
Apr 10
SJU1:29 amSan Juan Luis Munoz Marin Intl
5h 16m
ORD5:45 amChicago O'Hare Intl
$214
Spirit Airlines
Apr 16
ORD7:50 amChicago O'Hare Intl
16h 08m
1 stop
SJU12:58 amSan Juan Luis Munoz Marin Intl
Apr 25
SJU4:34 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD8:49 pmChicago O'Hare Intl
$215

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
Jun 6
ORD5:30 pmChicago O'Hare Intl
13h 34m
1 stop
SJU8:04 amSan Juan Luis Munoz Marin Intl
Jun 12
SJU6:11 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD10:26 pmChicago O'Hare Intl
$215
Frontier
Aug 26
ORD7:55 amChicago O'Hare Intl
7h 03m
1 stop
SJU3:58 pmSan Juan Luis Munoz Marin Intl
Sep 1
SJU6:11 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD10:26 pmChicago O'Hare Intl
$217
Frontier
Apr 6
ORD3:15 pmChicago O'Hare Intl
8h 46m
1 stop
SJU1:01 amSan Juan Luis Munoz Marin Intl
Apr 16
SJU11:30 amSan Juan Luis Munoz Marin Intl
13h 29m
1 stop
ORD11:59 pmChicago O'Hare Intl
$219

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 April 3, 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

Cheapest round-trip

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 5/31

12:33 am-6:24 am

Nonstop4h 51m

San Juan Luis Munoz Marin Intl

Thu 6/4

11:39 am-3:49 pm

Nonstop5h 10m

$214

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 6/6

5:30 pm-8:04 am

1 stop13h 34m

San Juan Luis Munoz Marin Intl

Fri 6/12

6:11 pm-10:26 pm

Nonstop5h 15m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 5/22

4:44 pm-10:21 pm

Nonstop4h 37m

San Juan Luis Munoz Marin Intl

Fri 5/29

6:00 am-12:37 pm

1 stop7h 37m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 4/19

10:00 am-3:39 pm

Nonstop4h 39m

San Juan Luis Munoz Marin Intl

Wed 4/22

12:57 pm-12:24 am

1 stop12h 27m

$219

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Mon 4/13

7:17 am-3:28 pm

1 stop7h 11m

Saint Thomas Island Cyril E King

Fri 4/17

5:10 pm-12:24 am

1 stop8h 14m

$259

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 8/1

12:12 pm-5:57 pm

Nonstop4h 45m

Punta Cana

Sat 8/8

7:02 am-11:12 am

Nonstop5h 10m

$299
Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 4/14

8:05 am-12:13 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Wed 4/22

1:15 pm-5:55 pm

Nonstop4h 40m

$318

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 4/14

7:22 am-1:19 pm

1 stop5h 57m

Montego Bay Sangster Intl

Wed 4/22

1:15 pm-5:55 pm

Nonstop4h 40m

$322

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 6/20

6:04 pm-11:25 am

2 stops41h 21m

George Town Owen Roberts Intl

Thu 6/25

12:25 pm-4:57 pm

1 stop28h 32m

$338

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 6/5

9:55 am-10:00 am

1 stop24h 05m

George Town Owen Roberts Intl

Mon 6/8

12:25 pm-9:05 am

1 stop20h 40m

$345

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 $317. 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 $354.

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 Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $383. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $460. 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 $376. 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 $489. 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 $389 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 $344 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 25m

Direct flights

Every day

Airports in Caribbean Islands

99 airports
The fastest flight from Chicago O'Hare Intl Airport to Caribbean Islands takes 3h 25m
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

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

  • 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
Spirit AirlinesPriceFrom $81Free CancellationRating
6.3
8,584 reviews
Search Spirit Airlines flights
FrontierPriceFrom $114Free CancellationRating
5.7
3,000 reviews
Search Frontier flights
JetBluePriceFrom $119Free CancellationRating
7.2
2,912 reviews
Search JetBlue flights
DeltaPriceFrom $143Free CancellationRating
7.9
8,382 reviews
Search Delta flights
Copa AirlinesPriceFrom $188Free CancellationRating
7.5
1,576 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $193Free CancellationRating
7.1
10,891 reviews
Search Air Canada flights
ArajetPriceFrom $199Free CancellationRating
6.5
47 reviews
Search Arajet flights
Hahn AirPriceFrom $213Free CancellationRating
0.0
Search Hahn Air flights
United AirlinesPriceFrom $254Free CancellationRating
7.4
9,542 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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