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Cheap flights from Chicago to Caribbean Islands from $80

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 to Caribbean Islands departing on 1/11. 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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0 bags

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Find the cheapest flights from Chicago to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Multiple Airlines Logo
8:00 am - 5:52 pm
SJU
-
ORD
11h 52m2 stops
$195Multiple Airlines
Wed, Jan 14 - Sat, Jan 17
JetBlue Logo
6:04 am - 4:56 pm
ORD
-
SJU
8h 52m1 stop
JetBlue Logo
5:10 am - 11:48 am
SJU
-
ORD
8h 38m1 stop
$196JetBlue
Sat, Feb 21 - Wed, Feb 25
Frontier Logo
8:00 am - 2:53 am
MDW
-
SJU
16h 53m1 stop
Frontier Logo
6:39 pm - 1:41 pm
SJU
-
MDW
20h 02m1 stop
$196Frontier
Sat, Feb 28 - Wed, Mar 11
Frontier Logo
7:30 am - 2:53 am
MDW
-
SJU
17h 23m1 stop
Frontier Logo
5:25 pm - 2:26 pm
SJU
-
MDW
23h 01m1 stop
$197Frontier
Thu, Feb 12 - Wed, Feb 18
Spirit Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Spirit Airlines Logo
1:22 pm - 4:37 pm
SJU
-
ORD
5h 15mnonstop
$197Spirit Airlines
Sun, Jan 25 - Fri, Feb 6
Spirit Airlines Logo
5:15 am - 4:37 pm
ORD
-
STT
9h 22m1 stop
Spirit Airlines Logo
5:42 pm - 11:47 pm
STT
-
ORD
8h 05m1 stop
$241Spirit Airlines
Wed, Feb 4 - Wed, Feb 11
Arajet Logo
10:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
$250Arajet
Sat, Feb 7 - Sat, Feb 14
Arajet Logo
10:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
$255Arajet
Sat, Feb 7 - Sat, Feb 14
American Airlines Logo
10:09 am - 3:22 pm
ORD
-
MBJ
4h 13mnonstop
American Airlines Logo
3:12 pm - 6:51 pm
MBJ
-
ORD
4h 39mnonstop
$377American Airlines
Mon, Jan 12 - Thu, Jan 15
American Airlines Logo
5:26 pm - 12:24 pm
ORD
-
MBJ
17h 58m1 stop
American Airlines Logo
3:12 pm - 6:51 pm
MBJ
-
ORD
4h 39mnonstop
$381American Airlines
Sat, Jan 24 - Thu, Jan 29

Frontier flights from Chicago to Caribbean Islands

Our best Frontier deals on Chicago to Caribbean Islands flight tickets
Frontier
Feb 28
MDW8:00 amChicago Midway
16h 53m
1 stop
SJU2:53 amSan Juan Luis Munoz Marin Intl
Mar 11
SJU6:39 pmSan Juan Luis Munoz Marin Intl
20h 02m
1 stop
MDW1:41 pmChicago Midway
$196
Find similar
Frontier
Feb 12
MDW7:30 amChicago Midway
17h 23m
1 stop
SJU2:53 amSan Juan Luis Munoz Marin Intl
Feb 18
SJU5:25 pmSan Juan Luis Munoz Marin Intl
23h 01m
1 stop
MDW2:26 pmChicago Midway
$197
Find similar
Frontier
Feb 7
ORD9:25 amChicago O'Hare Intl
12h 34m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
Feb 10
SJU5:25 pmSan Juan Luis Munoz Marin Intl
24h 27m
1 stop
ORD3:52 pmChicago O'Hare Intl
$198
Find similar

JetBlue flights from Chicago to Caribbean Islands

Our best JetBlue deals on Chicago to Caribbean Islands flight tickets
JetBlue
Feb 21
ORD6:04 amChicago O'Hare Intl
8h 52m
1 stop
SJU4:56 pmSan Juan Luis Munoz Marin Intl
Feb 25
SJU5:10 amSan Juan Luis Munoz Marin Intl
8h 38m
1 stop
ORD11:48 amChicago O'Hare Intl
$196
Find similar
JetBlue
Jan 23
ORD7:45 amChicago O'Hare Intl
8h 20m
1 stop
SJU6:05 pmSan Juan Luis Munoz Marin Intl
Jan 26
SJU11:06 amSan Juan Luis Munoz Marin Intl
10h 30m
1 stop
ORD7:36 pmChicago O'Hare Intl
$205
Find similar
JetBlue
May 14
ORD3:15 pmChicago O'Hare Intl
9h 44m
1 stop
SJU1:59 amSan Juan Luis Munoz Marin Intl
May 15
SJU12:30 pmSan Juan Luis Munoz Marin Intl
7h 56m
1 stop
ORD7:26 pmChicago O'Hare Intl
$210
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 December 23, 2025.
Use the filters below to find and compare flights from Chicago 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

Wed 1/14

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Sat 1/17

8:00 am-5:52 pm

2 stops11h 52m

$195

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

6:04 am-4:56 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

Wed 2/25

5:10 am-11:48 am

1 stop8h 38m

$196

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 2/28

8:00 am-2:53 am

1 stop16h 53m

San Juan Luis Munoz Marin Intl

Wed 3/11

6:39 pm-1:41 pm

1 stop20h 02m

$196

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 2/12

7:30 am-2:53 am

1 stop17h 23m

San Juan Luis Munoz Marin Intl

Wed 2/18

5:25 pm-2:26 pm

1 stop23h 01m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/25

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Fri 2/6

1:22 pm-4:37 pm

Nonstop5h 15m

$197

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 2/4

5:15 am-4:37 pm

1 stop9h 22m

Saint Thomas Island Cyril E King

Wed 2/11

5:42 pm-11:47 pm

1 stop8h 05m

$241

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 2/7

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 2/14

5:47 am-8:57 am

Nonstop5h 10m

$250

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 2/7

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 2/14

5:47 am-8:57 am

Nonstop5h 10m

$255

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 1/12

10:09 am-3:22 pm

Nonstop4h 13m

Montego Bay Sangster Intl

Thu 1/15

3:12 pm-6:51 pm

Nonstop4h 39m

$377

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 1/24

5:26 pm-12:24 pm

1 stop17h 58m

Montego Bay Sangster Intl

Thu 1/29

3:12 pm-6:51 pm

Nonstop4h 39m

$381

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 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, with most prices found around $346. The month of April is another great option to travel to Caribbean Islands, with average flight prices from Chicago averaging around $347.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Chicago 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 $386. If your travel schedule is flexible, try to avoid departing on a Friday 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 to Caribbean Islands in the evening for as low as $322. 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 $443. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago to Caribbean Islands flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago - 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 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 for as low as $338 on momondo.

What cabin class options are available on Chicago to Caribbean Islands flights?

There are 4 cabin classes available to choose from on Chicago 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 to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Chicago to Caribbean Islands.

Cheap Chicago to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Caribbean Islands

Fastest flight time

3h 25m

Direct flights

Every day

Airports in Caribbean Islands

99 airports
The fastest flight from Chicago to Caribbean Islands takes 3h 25m
Direct flights go from Chicago to Caribbean Islands every day.
There are 99 airports in Caribbean Islands. From Chicago there are direct flights to George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Montego Bay Sangster Intl (MBJ).
Search flight deals

  • When did momondo last update prices for flights from Chicago to Caribbean Islands?

    Prices for flights from Chicago to Caribbean Islands were last updated today.

  • How many operators does momondo search for flights from Chicago to Caribbean Islands?

  • How old do you have to be to fly from Chicago to Caribbean Islands?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Caribbean Islands?

Best airlines flying from Chicago to Caribbean Islands

Compare and see reviews for airlines that fly from Chicago to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $112Free CancellationRating
5.8
3,076 reviews
Search Frontier flights
JetBluePriceFrom $144Free CancellationRating
7.2
2,896 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $146Free CancellationRating
6.3
8,197 reviews
Search Spirit Airlines flights
DeltaPriceFrom $186Free CancellationRating
7.9
8,014 reviews
Search Delta flights
Copa AirlinesPriceFrom $188Free CancellationRating
7.6
1,558 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $215Free CancellationRating
7.4
9,105 reviews
Search United Airlines flights
ArajetPriceFrom $236Free CancellationRating
6.8
38 reviews
Search Arajet flights
SouthwestPriceFrom $277Free CancellationRating
8.0
4,253 reviews
Search Southwest flights
American AirlinesPriceFrom $337Free CancellationRating
7.2
11,054 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?

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Caribbean Islands right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Caribbean Islands, momondo offers a useful price alert feature which will track prices for flights to Caribbean Islands from Chicago and alert you when they change.

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.
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