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Cheap flights from Chicago O'Hare Intl Airport to Caribbean from $69

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 4/19. 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
5:05 am - 6:55 pm
ORD
-
SJU
12h 50m
1 stop
Spirit Airlines Logo
4:34 pm - 8:49 pm
SJU
-
ORD
5h 15mnonstop
$202Spirit Airlines
Mon, Apr 13 - Fri, Apr 17
Multiple Airlines Logo
7:17 am - 6:55 pm
ORD
-
SJU
10h 38m
1 stop
Multiple Airlines Logo
3:23 pm - 10:39 pm
SJU
-
ORD
8h 16m
1 stop
$203Multiple Airlines
Mon, Apr 13 - Fri, Apr 17
Multiple Airlines Logo
4:21 pm - 12:02 am
ORD
-
SJU
6h 41m
1 stop
Multiple Airlines Logo
1:29 am - 5:45 am
SJU
-
ORD
5h 16mnonstop
$205Multiple Airlines
Wed, Apr 8 - Mon, Apr 13
Frontier Logo
4:34 pm - 12:52 am
ORD
-
SJU
7h 18m
1 stop
Frontier Logo
3:23 pm - 10:39 pm
SJU
-
ORD
8h 16m
1 stop
$206Frontier
Tue, Apr 7 - Fri, Apr 17
Frontier Logo
6:04 pm - 9:54 am
ORD
-
SJU
14h 50m
1 stop
Frontier Logo
11:30 am - 11:59 pm
SJU
-
ORD
13h 29m
1 stop
$207Frontier
Fri, Apr 17 - Thu, Apr 23
Multiple Airlines Logo
11:55 am - 12:25 am
ORD
-
SJU
11h 30m
1 stop
Multiple Airlines Logo
1:29 am - 5:45 am
SJU
-
ORD
5h 16mnonstop
$208Multiple Airlines
Fri, Apr 10 - Mon, Apr 13
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
Mon, May 4 - Fri, May 8
American Airlines Logo
6:05 am - 1:25 pm
ORD
-
MBJ
7h 20m
1 stop
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
$322American Airlines
Mon, May 4 - Fri, May 8
United Airlines Logo
8:40 am - 12:50 pm
ORD
-
MBJ
4h 10mnonstop
United Airlines Logo
4:12 pm - 11:43 pm
MBJ
-
ORD
7h 31m
1 stop
$328United Airlines
Sun, Apr 26 - Wed, Apr 29
JetBlue Logo
6:00 am - 1:36 pm
ORD
-
CUR
30h 36m
2 stops
JetBlue Logo
3:15 pm - 9:36 pm
CUR
-
ORD
31h 21m
2 stops
$525JetBlue
Mon, May 4 - Fri, May 8

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
Apr 13
ORD5:05 amChicago O'Hare Intl
12h 50m
1 stop
SJU6:55 pmSan Juan Luis Munoz Marin Intl
Apr 17
SJU4:34 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD8:49 pmChicago O'Hare Intl
$202
Spirit Airlines
Apr 7
ORD10:55 amChicago O'Hare Intl
12h 03m
1 stop
SJU11:58 pmSan Juan Luis Munoz Marin Intl
Apr 13
SJU1:29 amSan Juan Luis Munoz Marin Intl
5h 16m
ORD5:45 amChicago O'Hare Intl
$212
Spirit Airlines
Apr 7
ORD10:55 amChicago O'Hare Intl
12h 03m
1 stop
SJU11:58 pmSan Juan Luis Munoz Marin Intl
Apr 15
SJU10:59 amSan Juan Luis Munoz Marin Intl
5h 09m
ORD3:08 pmChicago O'Hare Intl
$217

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
Apr 7
ORD4:34 pmChicago O'Hare Intl
7h 18m
1 stop
SJU12:52 amSan Juan Luis Munoz Marin Intl
Apr 17
SJU3:23 pmSan Juan Luis Munoz Marin Intl
8h 16m
1 stop
ORD10:39 pmChicago O'Hare Intl
$206
Frontier
Apr 17
ORD6:04 pmChicago O'Hare Intl
14h 50m
1 stop
SJU9:54 amSan Juan Luis Munoz Marin Intl
Apr 23
SJU11:30 amSan Juan Luis Munoz Marin Intl
13h 29m
1 stop
ORD11:59 pmChicago O'Hare Intl
$207
Frontier
Apr 30
ORD3:52 pmChicago O'Hare Intl
25h 07m
1 stop
SJU5:59 pmSan Juan Luis Munoz Marin Intl
May 4
SJU6:00 amSan Juan Luis Munoz Marin Intl
18h 55m
1 stop
ORD11:55 pmChicago O'Hare Intl
$209

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 March 23, 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

Cheapest round-trip

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 4/13

5:05 am-6:55 pm

1 stop12h 50m

San Juan Luis Munoz Marin Intl

Fri 4/17

4:34 pm-8:49 pm

Nonstop5h 15m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 4/13

7:17 am-6:55 pm

1 stop10h 38m

San Juan Luis Munoz Marin Intl

Fri 4/17

3:23 pm-10:39 pm

1 stop8h 16m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 4/8

4:21 pm-12:02 am

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Mon 4/13

1:29 am-5:45 am

Nonstop5h 16m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 4/7

4:34 pm-12:52 am

1 stop7h 18m

San Juan Luis Munoz Marin Intl

Fri 4/17

3:23 pm-10:39 pm

1 stop8h 16m

$206

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 4/17

6:04 pm-9:54 am

1 stop14h 50m

San Juan Luis Munoz Marin Intl

Thu 4/23

11:30 am-11:59 pm

1 stop13h 29m

$207

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 4/10

11:55 am-12:25 am

1 stop11h 30m

San Juan Luis Munoz Marin Intl

Mon 4/13

1:29 am-5:45 am

Nonstop5h 16m

$208
Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 5/4

8:05 am-12:13 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Fri 5/8

1:15 pm-5:55 pm

Nonstop4h 40m

$318

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 5/4

6:05 am-1:25 pm

1 stop7h 20m

Montego Bay Sangster Intl

Fri 5/8

1:15 pm-5:55 pm

Nonstop4h 40m

$322

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 4/26

8:40 am-12:50 pm

Nonstop4h 10m

Montego Bay Sangster Intl

Wed 4/29

4:12 pm-11:43 pm

1 stop7h 31m

$328

ChicagoWillemstad

ORD - CUR

ORDCUR

Chicago O'Hare Intl

Mon 5/4

6:00 am-1:36 pm

2 stops30h 36m

Willemstad Hato Int.

Fri 5/8

3:15 pm-9:36 pm

2 stops31h 21m

$525

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, September 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 $316. If you don’t want to visit Caribbean in September, then you should wait until May to fly from Chicago O'Hare Intl Airport, when ticket prices are also cheap, with an average price of $352.

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 $379. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $455. 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 $372. 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 $486.

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

Fly from Chicago O'Hare Intl to Punta Cana 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 $385 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 $335 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.

Can stopping save me money on Chicago O'Hare Intl Airport to Caribbean flights?

You could potentially save up to 22% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Caribbean flight.

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

$175

Fastest flight time

3h 24m

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 $175. The best round-trip flight deal from Chicago O'Hare Intl Airport to Caribbean found on momondo in the last 72 hours is $298.
The fastest flight from Chicago O'Hare Intl Airport to Caribbean takes 3h 24m
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 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
Spirit AirlinesPriceFrom $81Free CancellationRating
6.3
8,539 reviews
Search Spirit Airlines flights
FrontierPriceFrom $114Free CancellationRating
5.7
3,020 reviews
Search Frontier flights
JetBluePriceFrom $119Free CancellationRating
7.2
2,905 reviews
Search JetBlue flights
DeltaPriceFrom $143Free CancellationRating
7.9
8,317 reviews
Search Delta flights
Copa AirlinesPriceFrom $188Free CancellationRating
7.5
1,575 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $193Free CancellationRating
7.1
10,835 reviews
Search Air Canada flights
ArajetPriceFrom $198Free CancellationRating
6.5
47 reviews
Search Arajet flights
Hahn AirPriceFrom $213Free CancellationRating
0.0
Search Hahn Air flights
United AirlinesPriceFrom $254Free CancellationRating
7.4
9,464 reviews
Search United 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.

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Find better results for your trip to Caribbean

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Popular flights according to clicks in the last 7 days on momondo
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