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Cheap flights from Chicago to Caribbean Islands from $93

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 11/17. 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 to Caribbean Islands

Cheap round-trip flights

Spirit Airlines Logo
3:00 pm - 8:40 pmORD-SJU
4h 40mnonstop
Spirit Airlines Logo
3:19 pm - 9:33 pmSJU-ORD
7h 14m1 stop
$201Spirit Airlines
Find Deal
Sat, Oct 25 - Wed, Oct 29
Multiple Airlines Logo
9:06 pm - 2:51 amORD-SJU
4h 45mnonstop
Multiple Airlines Logo
10:39 pm - 4:23 pmSJU-ORD
19h 44m1 stop
$203Multiple Airlines
Find Deal
Fri, Oct 31 - Mon, Nov 3
United Airlines Logo
2:20 pm - 8:00 pmORD-SJU
4h 40mnonstop
United Airlines Logo
4:52 pm - 8:20 pmSJU-ORD
5h 28mnonstop
$218United Airlines
Find Deal
Tue, Oct 28 - Mon, Nov 3
American Airlines Logo
11:50 am - 11:59 pmORD-SJU
11h 09m1 stop
American Airlines Logo
5:30 am - 10:39 pmSJU-ORD
18h 09m1 stop
$222American Airlines
Find Deal
Tue, Oct 21 - Wed, Oct 22
United Airlines Logo
8:52 am - 2:44 pmORD-SJU
4h 52mnonstop
United Airlines Logo
1:05 am - 8:37 amSJU-ORD
8h 32m1 stop
$223United Airlines
Find Deal
Mon, Oct 20 - Fri, Oct 24
Delta Logo
7:00 am - 4:25 pmORD-SJU
8h 25m1 stop
Delta Logo
5:43 pm - 11:58 pmSJU-ORD
7h 15m1 stop
$227Delta
Find Deal
Tue, Oct 21 - Fri, Oct 24
Frontier Logo
5:56 pm - 5:54 pmMDW-SJU
22h 58m1 stop
Frontier Logo
10:39 pm - 8:32 amSJU-MDW
11h 53m1 stop
$237Frontier
Find Deal
Tue, Oct 28 - Sun, Nov 2
Frontier Logo
5:25 am - 2:54 amORD-SJU
19h 29m1 stop
Frontier Logo
2:11 am - 7:26 amSJU-ORD
7h 15m1 stop
$243Frontier
Find Deal
Thu, Nov 6 - Sun, Nov 9
American Airlines Logo
6:35 pm - 11:59 amORD-GCM
16h 24m1 stop
American Airlines Logo
3:35 pm - 6:45 pmGCM-ORD
4h 10mnonstop
$342American Airlines
Find Deal
Mon, Dec 15 - Fri, Dec 19
Delta Logo
5:32 am - 12:35 pmORD-GCM
6h 03m1 stop
Delta Logo
1:50 pm - 10:44 pmGCM-ORD
9h 54m1 stop
$352Delta
Find Deal
Mon, Dec 15 - Fri, Dec 19

Spirit Airlines flights from Chicago to Caribbean Islands

Our best Spirit Airlines deals on Chicago to Caribbean Islands flight tickets
Spirit Airlines
Oct 25
ORD3:00 pmChicago O'Hare Intl
4h 40m
SJU8:40 pmSan Juan Luis Munoz Marin Intl
Oct 29
SJU3:19 pmSan Juan Luis Munoz Marin Intl
7h 14m
1 stop
ORD9:33 pmChicago O'Hare Intl
$201
Find similar
Spirit Airlines
Sep 29
ORD6:30 amChicago O'Hare Intl
6h 41m
1 stop
SJU2:11 pmSan Juan Luis Munoz Marin Intl
Oct 8
SJU3:19 pmSan Juan Luis Munoz Marin Intl
7h 14m
1 stop
ORD9:33 pmChicago O'Hare Intl
$203
Find similar
Spirit Airlines
Nov 1
ORD2:03 pmChicago O'Hare Intl
4h 39m
SJU7:42 pmSan Juan Luis Munoz Marin Intl
Nov 19
SJU2:38 pmSan Juan Luis Munoz Marin Intl
5h 22m
ORD6:00 pmChicago O'Hare Intl
$205
Find similar

United Airlines flights from Chicago to Caribbean Islands

Our best United Airlines deals on Chicago to Caribbean Islands flight tickets
United Airlines
Oct 28
ORD2:20 pmChicago O'Hare Intl
4h 40m
SJU8:00 pmSan Juan Luis Munoz Marin Intl
Nov 3
SJU4:52 pmSan Juan Luis Munoz Marin Intl
5h 28m
ORD8:20 pmChicago O'Hare Intl
$218
Find similar
United Airlines
Oct 20
ORD8:52 amChicago O'Hare Intl
4h 52m
SJU2:44 pmSan Juan Luis Munoz Marin Intl
Oct 24
SJU1:05 amSan Juan Luis Munoz Marin Intl
8h 32m
1 stop
ORD8:37 amChicago O'Hare Intl
$223
Find similar
United Airlines
Jan 29
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM1:45 pmGeorge Town Owen Roberts Intl
Feb 2
GCM2:50 pmGeorge Town Owen Roberts Intl
4h 14m
ORD6:04 pmChicago O'Hare Intl
$341
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 September 22, 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

Sat 10/25

3:00 pm-8:40 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Wed 10/29

3:19 pm-9:33 pm

1 stop7h 14m

$201

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 10/31

9:06 pm-2:51 am

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Mon 11/3

10:39 pm-4:23 pm

1 stop19h 44m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 10/28

2:20 pm-8:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Mon 11/3

4:52 pm-8:20 pm

Nonstop5h 28m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 10/21

11:50 am-11:59 pm

1 stop11h 09m

San Juan Luis Munoz Marin Intl

Wed 10/22

5:30 am-10:39 pm

1 stop18h 09m

$222

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 10/20

8:52 am-2:44 pm

Nonstop4h 52m

San Juan Luis Munoz Marin Intl

Fri 10/24

1:05 am-8:37 am

1 stop8h 32m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 10/21

7:00 am-4:25 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Fri 10/24

5:43 pm-11:58 pm

1 stop7h 15m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 10/28

5:56 pm-5:54 pm

1 stop22h 58m

San Juan Luis Munoz Marin Intl

Sun 11/2

10:39 pm-8:32 am

1 stop11h 53m

$237

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 11/6

5:25 am-2:54 am

1 stop19h 29m

San Juan Luis Munoz Marin Intl

Sun 11/9

2:11 am-7:26 am

1 stop7h 15m

$243

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 12/15

6:35 pm-11:59 am

1 stop16h 24m

George Town Owen Roberts Intl

Fri 12/19

3:35 pm-6:45 pm

Nonstop4h 10m

$342

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 12/15

5:32 am-12:35 pm

1 stop6h 03m

George Town Owen Roberts Intl

Fri 12/19

1:50 pm-10:44 pm

1 stop9h 54m

$352

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 October is, on average, the cheapest month to fly to Caribbean Islands from Chicago, with most prices found around $329. The month of April is another great option to travel to Caribbean Islands, with average flight prices from Chicago averaging around $357.

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 $396. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $448. 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 $305. 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 $447. 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 Punta Cana 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 $388 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 $316 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 18m

Direct flights

Every day

Airports in Caribbean Islands

3 airports
The fastest flight from Chicago to Caribbean Islands takes 3h 18m
Direct flights go from Chicago to Caribbean Islands every day.
There are 3 airports near Caribbean Islands: George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Providenciales (PLS)
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 $106Free CancellationRating
5.8
3,166 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,031 reviews
Search Spirit Airlines flights
Copa AirlinesPriceFrom $188Free CancellationRating
7.6
1,536 reviews
Search Copa Airlines flights
DeltaPriceFrom $196Free CancellationRating
7.9
7,971 reviews
Search Delta flights
United AirlinesPriceFrom $215Free CancellationRating
7.4
8,922 reviews
Search United Airlines flights
ArajetPriceFrom $234Free CancellationRating
7.0
35 reviews
Search Arajet flights
JetBluePriceFrom $261Free CancellationRating
7.2
2,911 reviews
Search JetBlue flights
Air CanadaPriceFrom $335Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
American AirlinesPriceFrom $350Free CancellationRating
7.2
10,000 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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