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Cheap flights from Chicago O'Hare Intl Airport to Caribbean Islands from $107

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 9/21. 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

Discover deals from 900+ travel sites with momondo.

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.
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
$260Frontier
Fri, Aug 28 - Thu, Sep 3
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
$261Frontier
Mon, Aug 17 - Tue, Aug 18
American Airlines Logo
6:59 am - 9:55 pm
ORD
-
SJU
13h 56m
1 stop
American Airlines Logo
12:55 am - 5:00 am
SJU
-
ORD
5h 05mnonstop
$262American Airlines
Sat, Aug 15 - Fri, Aug 28
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
$264Frontier
Tue, Aug 4 - Wed, Aug 12
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
$265Frontier
Sun, Aug 16 - Sun, Aug 23
American Airlines Logo
7:11 pm - 1:00 pm
ORD
-
SDQ
16h 49m
1 stop
American Airlines Logo
2:00 pm - 11:44 pm
SDQ
-
ORD
10h 44m
1 stop
$388American Airlines
Wed, Aug 5 - Sat, Aug 8
Arajet Logo
12:12 pm - 5:57 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
$422Arajet
Sat, Sep 12 - Thu, Sep 17
Delta Logo
6:40 am - 3:34 pm
ORD
-
MBJ
8h 54m
1 stop
Delta Logo
4:59 pm - 7:56 am
MBJ
-
ORD
14h 57m
2 stops
$453Delta
Sun, Aug 16 - Thu, Aug 20
Delta Logo
5:10 pm - 2:10 pm
ORD
-
AUA
20h 00m
2 stops
Delta Logo
1:55 pm - 12:59 pm
AUA
-
ORD
24h 04m
2 stops
$646Delta
Sun, Sep 27 - Wed, Sep 30
United Airlines Logo
9:19 am - 3:35 pm
ORD
-
AUA
5h 16mnonstop
United Airlines Logo
1:50 pm - 6:38 pm
AUA
-
ORD
5h 48mnonstop
$647United Airlines
Fri, Jul 24 - Tue, Jul 28

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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
Aug 28
ORD12:44 amChicago O'Hare Intl
5h 00m
SJU6:44 amSan Juan Luis Munoz Marin Intl
Sep 3
SJU7:14 pmSan Juan Luis Munoz Marin Intl
5h 13m
ORD11:27 pmChicago O'Hare Intl
$260
Frontier
Aug 17
ORD12:44 amChicago O'Hare Intl
5h 00m
SJU6:44 amSan Juan Luis Munoz Marin Intl
Aug 18
SJU7:14 pmSan Juan Luis Munoz Marin Intl
5h 13m
ORD11:27 pmChicago O'Hare Intl
$261
Frontier
Jul 5
ORD12:44 amChicago O'Hare Intl
5h 00m
SJU6:44 amSan Juan Luis Munoz Marin Intl
Jul 15
SJU7:14 pmSan Juan Luis Munoz Marin Intl
5h 13m
ORD11:27 pmChicago O'Hare Intl
$264

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

Our best United Airlines deals on Chicago O'Hare Intl Airport to Caribbean Islands flight tickets
United Airlines
Jul 4
ORD8:02 pmChicago O'Hare Intl
8h 27m
1 stop
SJU5:29 amSan Juan Luis Munoz Marin Intl
Jul 10
SJU2:05 amSan Juan Luis Munoz Marin Intl
9h 15m
1 stop
ORD10:20 amChicago O'Hare Intl
$286
United Airlines
Jul 4
ORD8:02 pmChicago O'Hare Intl
8h 27m
1 stop
SJU5:29 amSan Juan Luis Munoz Marin Intl
Jul 7
SJU1:00 amSan Juan Luis Munoz Marin Intl
9h 00m
1 stop
ORD9:00 amChicago O'Hare Intl
$299
United Airlines
Jul 4
ORD8:02 pmChicago O'Hare Intl
8h 27m
1 stop
SJU5:29 amSan Juan Luis Munoz Marin Intl
Jul 7
SJU2:05 amSan Juan Luis Munoz Marin Intl
9h 15m
1 stop
ORD10:20 amChicago O'Hare Intl
$303

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 June 27, 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

Fri 8/28

12:44 am-6:44 am

Nonstop5h 00m

San Juan Luis Munoz Marin Intl

Thu 9/3

7:14 pm-11:27 pm

Nonstop5h 13m

$260

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 8/17

12:44 am-6:44 am

Nonstop5h 00m

San Juan Luis Munoz Marin Intl

Tue 8/18

7:14 pm-11:27 pm

Nonstop5h 13m

$261

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/15

6:59 am-9:55 pm

1 stop13h 56m

San Juan Luis Munoz Marin Intl

Fri 8/28

12:55 am-5:00 am

Nonstop5h 05m

$262

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/4

12:44 am-6:44 am

Nonstop5h 00m

San Juan Luis Munoz Marin Intl

Wed 8/12

7:14 pm-11:27 pm

Nonstop5h 13m

$264

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/16

12:44 am-6:44 am

Nonstop5h 00m

San Juan Luis Munoz Marin Intl

Sun 8/23

7:14 pm-11:27 pm

Nonstop5h 13m

$265

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Wed 8/5

7:11 pm-1:00 pm

1 stop16h 49m

Santo Domingo Las Americas

Sat 8/8

2:00 pm-11:44 pm

1 stop10h 44m

$388
Quickest round-trip

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 9/12

12:12 pm-5:57 pm

Nonstop4h 45m

Punta Cana

Thu 9/17

7:30 pm-11:40 pm

Nonstop5h 10m

$422

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 8/16

6:40 am-3:34 pm

1 stop8h 54m

Montego Bay Sangster Intl

Thu 8/20

4:59 pm-7:56 am

2 stops14h 57m

$453

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

Sun 9/27

5:10 pm-2:10 pm

2 stops20h 00m

Oranjestad Reina Beatrix

Wed 9/30

1:55 pm-12:59 pm

2 stops24h 04m

$646

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

Fri 7/24

9:19 am-3:35 pm

Nonstop5h 16m

Oranjestad Reina Beatrix

Tue 7/28

1:50 pm-6:38 pm

Nonstop5h 48m

$647

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 $186. 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 $466.

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 $436. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $544. 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 $388. 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 $527. 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 from Chicago O'Hare Intl Airport 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 $394 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 $353 on momondo.

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

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

You could potentially save up to 27% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Caribbean Islands flight.

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 George Town Owen Roberts Intl (GCM), 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
DeltaPriceFrom $118Free CancellationRating
7.8
8,453 reviews
Search Delta flights
JetBluePriceFrom $119Free CancellationRating
7.1
3,014 reviews
Search JetBlue flights
FrontierPriceFrom $144Free CancellationRating
5.6
2,862 reviews
Search Frontier flights
Air CanadaPriceFrom $175Free CancellationRating
7.1
11,268 reviews
Search Air Canada flights
ArajetPriceFrom $216Free CancellationRating
6.5
49 reviews
Search Arajet flights
Hahn AirPriceFrom $228Free CancellationRating
0.0
Search Hahn Air flights
United AirlinesPriceFrom $262Free CancellationRating
7.4
9,896 reviews
Search United Airlines flights
American AirlinesPriceFrom $300Free CancellationRating
7.1
11,776 reviews
Search American Airlines flights
AviancaPriceFrom $324Free CancellationRating
6.5
2,537 reviews
Search Avianca 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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