Cheap flights from Illinois to Caribbean Islands from $87

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Caribbean Islands departing on 3/3. 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

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Find the cheapest flights from Illinois to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
12:18 pm - 5:54 pm
ORD
-
SJU
4h 36mnonstop
Spirit Airlines Logo
12:30 pm - 4:38 pm
SJU
-
ORD
5h 08mnonstop
$179Spirit Airlines
Mon, Apr 20 - Thu, Apr 23
Spirit Airlines Logo
5:15 am - 3:31 pm
ORD
-
SJU
8h 16m
1 stop
Spirit Airlines Logo
11:52 am - 6:18 pm
SJU
-
ORD
8h 26m
1 stop
$181Spirit Airlines
Sun, Mar 1 - Thu, Mar 5
Frontier Logo
1:27 pm - 12:33 pm
ORD
-
SJU
22h 06m
1 stop
Frontier Logo
6:00 am - 10:57 pm
SJU
-
ORD
17h 57m
1 stop
$184Frontier
Sat, May 9 - Fri, May 15
Multiple Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Multiple Airlines Logo
3:22 pm - 10:39 pm
SJU
-
ORD
8h 17m
1 stop
$185Multiple Airlines
Tue, Feb 24 - Mon, Mar 9
Multiple Airlines Logo
6:00 am - 2:22 pm
MDW
-
SJU
30h 22m
1 stop
Multiple Airlines Logo
6:27 pm - 6:38 pm
SJU
-
MDW
26h 11m
1 stop
$188Multiple Airlines
Mon, Feb 23 - Thu, Feb 26
Frontier Logo
2:56 pm - 12:14 am
MDW
-
SJU
8h 18m
1 stop
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
$202Frontier
Sat, Apr 11 - Fri, Apr 17
Arajet Logo
6:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 9:57 am
PUJ
-
ORD
5h 10mnonstop
$278Arajet
Mon, Mar 9 - Sat, Mar 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
$284Arajet
Sat, Feb 28 - Sat, Mar 7
Air Canada Logo
3:45 pm - 5:25 pm
ORD
-
PLS
24h 40m
1 stop
Air Canada Logo
6:40 pm - 2:55 pm
PLS
-
ORD
21h 15m
1 stop
$345Air Canada
Wed, Apr 22 - Tue, Apr 28
Air Canada Logo
8:40 pm - 12:20 pm
ORD
-
PLS
14h 40m
1 stop
Air Canada Logo
6:40 pm - 10:53 am
PLS
-
ORD
17h 13m
1 stop
$350Air Canada
Wed, Mar 25 - Tue, Mar 31

Spirit Airlines flights from Illinois to Caribbean Islands

Our best Spirit Airlines deals on Illinois to Caribbean Islands flight tickets
Spirit Airlines
Apr 20
ORD12:18 pmChicago O'Hare Intl
4h 36m
SJU5:54 pmSan Juan Luis Munoz Marin Intl
Apr 23
SJU12:30 pmSan Juan Luis Munoz Marin Intl
5h 08m
ORD4:38 pmChicago O'Hare Intl
$179
Spirit Airlines
Feb 22
ORD12:17 pmChicago O'Hare Intl
4h 32m
SJU6:49 pmSan Juan Luis Munoz Marin Intl
Feb 26
SJU11:52 amSan Juan Luis Munoz Marin Intl
8h 26m
1 stop
ORD6:18 pmChicago O'Hare Intl
$182
Spirit Airlines
Feb 23
ORD12:17 pmChicago O'Hare Intl
4h 32m
SJU6:49 pmSan Juan Luis Munoz Marin Intl
Mar 6
SJU11:52 amSan Juan Luis Munoz Marin Intl
8h 26m
1 stop
ORD6:18 pmChicago O'Hare Intl
$187

Frontier flights from Illinois to Caribbean Islands

Our best Frontier deals on Illinois to Caribbean Islands flight tickets
Frontier
May 9
ORD1:27 pmChicago O'Hare Intl
22h 06m
1 stop
SJU12:33 pmSan Juan Luis Munoz Marin Intl
May 15
SJU6:00 amSan Juan Luis Munoz Marin Intl
17h 57m
1 stop
ORD10:57 pmChicago O'Hare Intl
$184
Frontier
Mar 4
ORD8:30 amChicago O'Hare Intl
16h 23m
1 stop
SJU2:53 amSan Juan Luis Munoz Marin Intl
Mar 11
SJU6:30 amSan Juan Luis Munoz Marin Intl
18h 08m
1 stop
ORD11:38 pmChicago O'Hare Intl
$199
Frontier
May 9
STL4:55 pmLambert-St Louis
8h 06m
1 stop
SJU2:01 amSan Juan Luis Munoz Marin Intl
May 13
SJU3:19 pmSan Juan Luis Munoz Marin Intl
9h 00m
1 stop
STL11:19 pmLambert-St Louis
$202

momondo Fare Finder

 
Customize your flight search to find flights from Illinois 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 February 13, 2026.
Use the filters below to find and compare flights from Illinois 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 4/20

12:18 pm-5:54 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

Thu 4/23

12:30 pm-4:38 pm

Nonstop5h 08m

$179

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 3/1

5:15 am-3:31 pm

1 stop8h 16m

San Juan Luis Munoz Marin Intl

Thu 3/5

11:52 am-6:18 pm

1 stop8h 26m

$181

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/9

1:27 pm-12:33 pm

1 stop22h 06m

San Juan Luis Munoz Marin Intl

Fri 5/15

6:00 am-10:57 pm

1 stop17h 57m

$184

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 2/24

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Mon 3/9

3:22 pm-10:39 pm

1 stop8h 17m

$185

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/23

6:00 am-2:22 pm

1 stop30h 22m

San Juan Luis Munoz Marin Intl

Thu 2/26

6:27 pm-6:38 pm

1 stop26h 11m

$188

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 4/11

2:56 pm-12:14 am

1 stop8h 18m

San Juan Luis Munoz Marin Intl

Fri 4/17

3:18 pm-10:19 pm

1 stop8h 01m

$202

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 3/9

6:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Sat 3/14

5:47 am-9:57 am

Nonstop5h 10m

$278

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 2/28

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 3/7

5:47 am-8:57 am

Nonstop5h 10m

$284

ChicagoProvidenciales

ORD - PLS

ORDPLS

Chicago O'Hare Intl

Wed 4/22

3:45 pm-5:25 pm

1 stop24h 40m

Providenciales

Tue 4/28

6:40 pm-2:55 pm

1 stop21h 15m

$345

ChicagoProvidenciales

ORD - PLS

ORDPLS

Chicago O'Hare Intl

Wed 3/25

8:40 pm-12:20 pm

1 stop14h 40m

Providenciales

Tue 3/31

6:40 pm-10:53 am

1 stop17h 13m

$350

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 Illinois 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 April is, on average, the cheapest month to fly to Caribbean Islands from Illinois, with most prices found around $323. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Illinois averaging around $348.

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

The cheapest day to depart from Illinois 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 $381. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $446. 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 Illinois to Caribbean Islands in the evening for as low as $326. 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 at noon because they tend to be around $479. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Illinois to Caribbean Islands flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Illinois - 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 Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands 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 Islands from Illinois for as low as $328 on momondo.

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

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

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

Cheap Illinois to Caribbean Islands flight deals and tips

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

Fastest flight time

3h 24m

Direct flights

Every day

Airports in Caribbean Islands

99 airports
The fastest flight from Illinois to Caribbean Islands takes 3h 24m
Direct flights go from Illinois to Caribbean Islands every day.
There are 99 airports in Caribbean Islands. From Illinois there are direct flights to Nassau Intl (NAS).
  • When did momondo last update prices for flights from Illinois to Caribbean Islands?

    Prices for flights from Illinois to Caribbean Islands are updated daily.

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

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

Best airlines flying from Illinois to Caribbean Islands

Compare and see reviews for airlines that fly from Illinois to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $106Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
JetBluePriceFrom $119Free CancellationRating
7.2
2,897 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $130Free CancellationRating
6.3
8,450 reviews
Search Spirit Airlines flights
DeltaPriceFrom $132Free CancellationRating
7.9
8,196 reviews
Search Delta flights
ArajetPriceFrom $180Free CancellationRating
6.6
43 reviews
Search Arajet flights
Copa AirlinesPriceFrom $188Free CancellationRating
7.5
1,559 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $193Free CancellationRating
7.1
10,717 reviews
Search Air Canada flights
Hahn AirPriceFrom $213Free CancellationRating
0.0
Search Hahn Air flights
American AirlinesPriceFrom $225Free CancellationRating
7.2
11,282 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Caribbean Islands?

Finding the right flight to Caribbean Islands from Illinois is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Caribbean Islands quick and easy, saving you time and money.

Can I find flights from Illinois to Caribbean Islands with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Illinois to Caribbean Islands flights to just show those with flexible booking policies.

How can momondo help me find flights from Illinois 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 Illinois.

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

Of course. momondo tracks the price of Illinois to Caribbean Islands flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Caribbean Islands trip

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1 adult
Sun 3/15
Sun 3/22

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Popular cities in Caribbean Islands

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