Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago O'Hare Intl Airport to Caribbean Islands from $68

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 12/10. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
12:22 pm - 6:54 pmORD-SJU
4h 32mnonstop
Multiple Airlines Logo
4:11 pm - 11:35 pmSJU-ORD
9h 24m1 stop
$211Multiple Airlines
Find Deal
vie., feb. 20 - vie., feb. 27
Multiple Airlines Logo
2:00 pm - 12:49 amORD-SJU
8h 49m1 stop
Multiple Airlines Logo
8:45 pm - 11:59 pmSJU-ORD
5h 14mnonstop
$212Multiple Airlines
Find Deal
vie., dic. 5 - dom., dic. 14
Frontier Logo
6:40 am - 5:54 pmORD-SJU
9h 14m1 stop
Frontier Logo
4:11 pm - 10:23 pmSJU-ORD
8h 12m1 stop
$213Frontier
Find Deal
jue., feb. 19 - mar., mar. 3
Frontier Logo
5:50 am - 3:19 pmORD-SJU
7h 29m1 stop
Frontier Logo
8:57 am - 2:39 pmSJU-ORD
7h 42m1 stop
$215Frontier
Find Deal
dom., ene. 11 - sáb., ene. 17
Delta Logo
6:25 pm - 11:55 amORD-NAS
16h 30m1 stop
Delta Logo
6:27 pm - 11:57 pmNAS-ORD
6h 30m1 stop
$355Delta
Find Deal
dom., feb. 1 - jue., feb. 5
Delta Logo
6:30 pm - 12:55 pmORD-AUA
16h 25m1 stop
Delta Logo
4:25 pm - 11:49 pmAUA-ORD
9h 24m1 stop
$356Delta
Find Deal
dom., feb. 15 - jue., feb. 26
American Airlines Logo
7:07 pm - 11:07 amORD-NAS
15h 00m1 stop
American Airlines Logo
12:09 pm - 7:31 pmNAS-ORD
8h 22m1 stop
$360American Airlines
Find Deal
vie., dic. 5 - dom., dic. 14
American Airlines Logo
5:26 pm - 12:43 pmORD-AUA
17h 17m1 stop
American Airlines Logo
2:59 pm - 10:10 amAUA-ORD
21h 11m1 stop
$363American Airlines
Find Deal
sáb., feb. 7 - mié., feb. 11
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
United Airlines Logo
2:48 pm - 6:13 pmMBJ-ORD
4h 25mnonstop
$364United Airlines
Find Deal
sáb., dic. 13 - dom., dic. 21
United Airlines Logo
10:30 am - 3:03 pmORD-NAS
3h 33mnonstop
United Airlines Logo
3:35 pm - 6:35 pmNAS-ORD
4h 00mnonstop
$370United Airlines
Find Deal
sáb., ene. 31 - vie., feb. 6

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

Our best American Airlines deals on Chicago O'Hare Intl Airport to Caribbean Islands flight tickets
American Airlines
Feb 7
ORD7:30 pmChicago O'Hare Intl
13h 18m
1 stop
SJU10:48 amSan Juan Luis Munoz Marin Intl
Feb 12
SJU4:07 pmSan Juan Luis Munoz Marin Intl
5h 38m
ORD7:45 pmChicago O'Hare Intl
$223
Find similar
American Airlines
Dec 2
ORD9:50 amChicago O'Hare Intl
4h 37m
PUJ4:27 pmPunta Cana
Dec 5
PUJ1:02 pmPunta Cana
5h 21m
ORD4:23 pmChicago O'Hare Intl
$268
Find similar
American Airlines
Feb 17
ORD10:22 amChicago O'Hare Intl
4h 07m
MBJ3:29 pmMontego Bay Sangster Intl
Feb 24
MBJ2:14 pmMontego Bay Sangster Intl
4h 46m
ORD6:00 pmChicago O'Hare Intl
$365
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
Feb 19
ORD6:40 amChicago O'Hare Intl
9h 14m
1 stop
SJU5:54 pmSan Juan Luis Munoz Marin Intl
Mar 3
SJU4:11 pmSan Juan Luis Munoz Marin Intl
8h 12m
1 stop
ORD10:23 pmChicago O'Hare Intl
$213
Find similar
Frontier
Jan 11
ORD5:50 amChicago O'Hare Intl
7h 29m
1 stop
SJU3:19 pmSan Juan Luis Munoz Marin Intl
Jan 17
SJU8:57 amSan Juan Luis Munoz Marin Intl
7h 42m
1 stop
ORD2:39 pmChicago O'Hare Intl
$215
Find similar
Frontier
Jan 10
ORD6:11 pmChicago O'Hare Intl
14h 06m
1 stop
SJU10:17 amSan Juan Luis Munoz Marin Intl
Jan 15
SJU4:06 pmSan Juan Luis Munoz Marin Intl
10h 06m
1 stop
ORD12:12 amChicago O'Hare Intl
$216
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 noviembre 13, 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

vie. 2/20

12:22 pm-6:54 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

vie. 2/27

4:11 pm-11:35 pm

1 stop9h 24m

$211

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

vie. 12/5

2:00 pm-12:49 am

1 stop8h 49m

San Juan Luis Munoz Marin Intl

dom. 12/14

8:45 pm-11:59 pm

Nonstop5h 14m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

jue. 2/19

6:40 am-5:54 pm

1 stop9h 14m

San Juan Luis Munoz Marin Intl

mar. 3/3

4:11 pm-10:23 pm

1 stop8h 12m

$213

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

dom. 1/11

5:50 am-3:19 pm

1 stop7h 29m

San Juan Luis Munoz Marin Intl

sáb. 1/17

8:57 am-2:39 pm

1 stop7h 42m

$215

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

dom. 2/1

6:25 pm-11:55 am

1 stop16h 30m

Nassau Intl

jue. 2/5

6:27 pm-11:57 pm

1 stop6h 30m

$355

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

dom. 2/15

6:30 pm-12:55 pm

1 stop16h 25m

Oranjestad Reina Beatrix

jue. 2/26

4:25 pm-11:49 pm

1 stop9h 24m

$356

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

vie. 12/5

7:07 pm-11:07 am

1 stop15h 00m

Nassau Intl

dom. 12/14

12:09 pm-7:31 pm

1 stop8h 22m

$360

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

sáb. 2/7

5:26 pm-12:43 pm

1 stop17h 17m

Oranjestad Reina Beatrix

mié. 2/11

2:59 pm-10:10 am

1 stop21h 11m

$363

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sáb. 12/13

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

dom. 12/21

2:48 pm-6:13 pm

Nonstop4h 25m

$364

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

sáb. 1/31

10:30 am-3:03 pm

Nonstop3h 33m

Nassau Intl

vie. 2/6

3:35 pm-6:35 pm

Nonstop4h 00m

$370

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 January is, on average, the cheapest month to fly to Caribbean Islands from Chicago O'Hare Intl Airport, with most prices found around $320. 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 $347.

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 $393. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $444. 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 $314. 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 $450. 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 Punta Cana 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 $392 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 $335 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
3,110 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,139 reviews
Search Spirit Airlines flights
DeltaPriceFrom $186Free CancellationRating
7.9
8,007 reviews
Search Delta flights
Copa AirlinesPriceFrom $188Free CancellationRating
7.6
1,565 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
9,017 reviews
Search United Airlines flights
ArajetPriceFrom $233Free CancellationRating
7.1
36 reviews
Search Arajet flights
JetBluePriceFrom $261Free CancellationRating
7.2
2,907 reviews
Search JetBlue flights
Air CanadaPriceFrom $335Free CancellationRating
7.1
10,448 reviews
Search Air Canada flights
American AirlinesPriceFrom $344Free CancellationRating
7.2
11,051 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
sáb. 12/13
sáb. 12/20
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $44
Flights to Londonfrom $313
Flights to Bangkokfrom $507
Flights to Tokyofrom $448
Flights to Los Angelesfrom $49
Flights to Parisfrom $340
Flights to Copenhagenfrom $359
Flights to Istanbulfrom $374
Flights to Manilafrom $497
Flights to Romefrom $321
Flights to Miamifrom $49
Flights to Chicagofrom $58