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Cheap flights from Chicago to Caribbean Islands from $91

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 8/18. 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
6:23 pm - 12:06 amORD-SJU
4h 43mnonstop
Spirit Airlines Logo
10:16 pm - 9:22 amSJU-ORD
12h 06m1 stop
$189Spirit Airlines
Find Deal
Mon, Aug 11 - Fri, Aug 15
Spirit Airlines Logo
12:55 pm - 6:34 pmORD-SJU
4h 39mnonstop
Spirit Airlines Logo
7:40 pm - 11:56 pmSJU-ORD
5h 16mnonstop
$190Spirit Airlines
Find Deal
Thu, Sep 25 - Mon, Sep 29
Frontier Logo
10:51 am - 7:18 pmMDW-SJU
7h 27m1 stop
Frontier Logo
3:39 am - 9:51 amSJU-MDW
7h 12m1 stop
$235Frontier
Find Deal
Sat, Aug 30 - Fri, Sep 5
Frontier Logo
10:51 am - 11:59 pmMDW-SJU
12h 08m1 stop
Frontier Logo
3:39 am - 9:51 amSJU-MDW
7h 12m1 stop
$238Frontier
Find Deal
Sat, Sep 6 - Fri, Sep 19
American Airlines Logo
6:03 am - 2:15 pmORD-PUJ
7h 12m1 stop
American Airlines Logo
3:30 pm - 7:30 pmPUJ-ORD
5h 00mnonstop
$307American Airlines
Find Deal
Mon, Aug 18 - Wed, Aug 27
American Airlines Logo
8:35 am - 2:15 pmORD-PUJ
4h 40mnonstop
American Airlines Logo
3:30 pm - 7:30 pmPUJ-ORD
5h 00mnonstop
$327American Airlines
Find Deal
Mon, Aug 18 - Wed, Aug 27
Southwest Logo
11:40 am - 10:40 pmMDW-SJU
10h 00m1 stop
Southwest Logo
7:45 am - 3:35 pmSJU-MDW
8h 50m2 stops
$351Southwest
Find Deal
Sat, Sep 6 - Sat, Sep 13
Southwest Logo
6:35 am - 4:40 pmMDW-SJU
9h 05m1 stop
Southwest Logo
5:50 am - 1:20 pmSJU-MDW
8h 30m2 stops
$357Southwest
Find Deal
Thu, Oct 9 - Mon, Oct 13
Delta Logo
6:00 am - 3:34 pmMDW-MBJ
9h 34m1 stop
Delta Logo
4:59 pm - 12:28 pmMBJ-MDW
19h 29m2 stops
$389Delta
Find Deal
Sun, Sep 21 - Fri, Sep 26
Delta Logo
6:00 am - 3:36 pmMDW-MBJ
9h 36m1 stop
Delta Logo
1:20 pm - 9:12 pmMBJ-MDW
7h 52m1 stop
$410Delta
Find Deal
Mon, Sep 1 - Sat, Sep 6

Spirit Airlines flights from Chicago to Caribbean Islands

Our best Spirit Airlines deals on Chicago to Caribbean Islands flight tickets
Spirit Airlines
Aug 11
ORD6:23 pmChicago O'Hare Intl
4h 43m
SJU12:06 amSan Juan Luis Munoz Marin Intl
Aug 15
SJU10:16 pmSan Juan Luis Munoz Marin Intl
12h 06m
1 stop
ORD9:22 amChicago O'Hare Intl
$189
Find similar
Spirit Airlines
Sep 25
ORD12:55 pmChicago O'Hare Intl
4h 39m
SJU6:34 pmSan Juan Luis Munoz Marin Intl
Sep 29
SJU7:40 pmSan Juan Luis Munoz Marin Intl
5h 16m
ORD11:56 pmChicago O'Hare Intl
$190
Find similar
Spirit Airlines
Nov 6
ORD6:55 amChicago O'Hare Intl
4h 38m
SJU1:33 pmSan Juan Luis Munoz Marin Intl
Nov 13
SJU2:38 pmSan Juan Luis Munoz Marin Intl
5h 22m
ORD6:00 pmChicago O'Hare Intl
$191
Find similar

Frontier flights from Chicago to Caribbean Islands

Our best Frontier deals on Chicago to Caribbean Islands flight tickets
Frontier
Aug 30
MDW10:51 amChicago Midway
7h 27m
1 stop
SJU7:18 pmSan Juan Luis Munoz Marin Intl
Sep 5
SJU3:39 amSan Juan Luis Munoz Marin Intl
7h 12m
1 stop
MDW9:51 amChicago Midway
$235
Find similar
Frontier
Sep 6
MDW10:51 amChicago Midway
12h 08m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
Sep 19
SJU3:39 amSan Juan Luis Munoz Marin Intl
7h 12m
1 stop
MDW9:51 amChicago Midway
$238
Find similar
Frontier
Aug 30
MDW10:51 amChicago Midway
21h 08m
1 stop
SJU8:59 amSan Juan Luis Munoz Marin Intl
Sep 6
SJU4:42 pmSan Juan Luis Munoz Marin Intl
17h 36m
1 stop
MDW9:18 amChicago Midway
$239
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 July 31, 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

Mon 8/11

6:23 pm-12:06 am

Nonstop4h 43m

San Juan Luis Munoz Marin Intl

Fri 8/15

10:16 pm-9:22 am

1 stop12h 06m

$189

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 9/25

12:55 pm-6:34 pm

Nonstop4h 39m

San Juan Luis Munoz Marin Intl

Mon 9/29

7:40 pm-11:56 pm

Nonstop5h 16m

$190

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/30

10:51 am-7:18 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-9:51 am

1 stop7h 12m

$235

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/6

10:51 am-11:59 pm

1 stop12h 08m

San Juan Luis Munoz Marin Intl

Fri 9/19

3:39 am-9:51 am

1 stop7h 12m

$238

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 8/18

6:03 am-2:15 pm

1 stop7h 12m

Punta Cana

Wed 8/27

3:30 pm-7:30 pm

Nonstop5h 00m

$307

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 8/18

8:35 am-2:15 pm

Nonstop4h 40m

Punta Cana

Wed 8/27

3:30 pm-7:30 pm

Nonstop5h 00m

$327

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/6

11:40 am-10:40 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Sat 9/13

7:45 am-3:35 pm

2 stops8h 50m

$351

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/9

6:35 am-4:40 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Mon 10/13

5:50 am-1:20 pm

2 stops8h 30m

$357

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 9/21

6:00 am-3:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

Fri 9/26

4:59 pm-12:28 pm

2 stops19h 29m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 9/1

6:00 am-3:36 pm

1 stop9h 36m

Montego Bay Sangster Intl

Sat 9/6

1:20 pm-9:12 pm

1 stop7h 52m

$410

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 September is, on average, the cheapest month to fly to Caribbean Islands from Chicago, with most prices found around $295. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Chicago averaging around $313.

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 $395. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $449. 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 $303. 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 $444. 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 $375 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 $302 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

Best Price Found

$91

Fastest flight time

3h 18m

Direct flights

Every day

Airports in Caribbean Islands

6 airports
The best one-way flight to Caribbean Islands from Chicago in the past 72 hours is $91. The best round-trip flight deal from Chicago to Caribbean Islands found on momondo in the last 72 hours is $189.
The fastest flight from Chicago to Caribbean Islands takes 3h 18m
Direct flights go from Chicago to Caribbean Islands every day.
There are 6 airports near Caribbean Islands: Nassau Intl (NAS), Saint Thomas Island Cyril E King (STT), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Providenciales (PLS), San Juan Luis Munoz Marin Intl (SJU)
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  • 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
5.9
3,239 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,048 reviews
Search Spirit Airlines flights
DeltaPriceFrom $190Free CancellationRating
8.0
7,981 reviews
Search Delta flights
Copa AirlinesPriceFrom $193Free CancellationRating
7.5
1,493 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
ArajetPriceFrom $235Free CancellationRating
7.1
32 reviews
Search Arajet flights
JetBluePriceFrom $261Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
Air CanadaPriceFrom $335Free CancellationRating
7.1
9,851 reviews
Search Air Canada flights
American AirlinesPriceFrom $346Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $352Free CancellationRating
8.0
4,246 reviews
Search Southwest 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

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