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Cheap flights from Illinois to Caribbean from $98

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 departing on 9/20. 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 Illinois to Caribbean

Cheap round-trip flights

Frontier Logo
6:40 am - 3:24 pmORD-SJU
7h 44m1 stop
Frontier Logo
3:40 am - 3:39 pmSJU-ORD
12h 59m1 stop
$216Frontier
Find Deal
Sat, Oct 11 - Fri, Oct 17
Spirit Airlines Logo
5:05 am - 9:48 pmORD-SJU
15h 43m1 stop
Spirit Airlines Logo
7:40 pm - 11:56 pmSJU-ORD
5h 16mnonstop
$220Spirit Airlines
Find Deal
Sun, Aug 31 - Fri, Sep 5
Logo
8:56 pm - 2:17 pmORD-SJU
16h 21m1 stop
Logo
3:39 am - 3:17 pmSJU-ORD
12h 38m1 stop
$228
Find Deal
Sat, Sep 20 - Fri, Sep 26
Logo
6:30 am - 2:11 pmORD-SJU
6h 41m1 stop
Logo
3:39 am - 3:17 pmSJU-ORD
12h 38m1 stop
$233
Find Deal
Wed, Sep 17 - Fri, Sep 19
American Airlines Logo
8:35 am - 2:05 pmORD-PUJ
4h 30mnonstop
American Airlines Logo
4:25 pm - 11:12 pmPUJ-ORD
7h 47m1 stop
$338American Airlines
Find Deal
Tue, Sep 2 - Tue, Sep 9
Southwest Logo
6:25 am - 2:20 pmMDW-PUJ
6h 55m1 stop
Southwest Logo
3:30 pm - 10:20 pmPUJ-MDW
7h 50m1 stop
$343Southwest
Find Deal
Sun, Oct 5 - Fri, Oct 10
American Airlines Logo
8:35 am - 2:00 pmORD-PUJ
4h 25mnonstop
American Airlines Logo
3:21 pm - 7:36 pmPUJ-ORD
5h 15mnonstop
$346American Airlines
Find Deal
Mon, Oct 6 - Fri, Oct 10
Delta Logo
6:00 am - 2:32 pmMDW-PUJ
7h 32m1 stop
Delta Logo
1:57 pm - 9:48 amPUJ-MDW
20h 51m2 stops
$347Delta
Find Deal
Tue, Sep 23 - Fri, Sep 26
Delta Logo
5:20 am - 1:24 pmORD-PUJ
7h 04m1 stop
Delta Logo
1:53 pm - 7:50 amPUJ-ORD
18h 57m2 stops
$347Delta
Find Deal
Mon, Oct 27 - Tue, Oct 28
Southwest Logo
7:05 am - 2:30 pmMDW-PUJ
6h 25m1 stop
Southwest Logo
1:40 pm - 10:35 pmPUJ-MDW
9h 55m1 stop
$368Southwest
Find Deal
Fri, Oct 24 - Wed, Oct 29

Spirit Airlines flights from Illinois to Caribbean

Our best Spirit Airlines deals on Illinois to Caribbean flight tickets
Spirit Airlines
Aug 31
ORD5:05 amChicago O'Hare Intl
15h 43m
1 stop
SJU9:48 pmSan Juan Luis Munoz Marin Intl
Sep 5
SJU7:40 pmSan Juan Luis Munoz Marin Intl
5h 16m
ORD11:56 pmChicago O'Hare Intl
$220
Find similar
Spirit Airlines
Aug 31
ORD5:05 amChicago O'Hare Intl
15h 43m
1 stop
SJU9:48 pmSan Juan Luis Munoz Marin Intl
Sep 5
SJU7:40 pmSan Juan Luis Munoz Marin Intl
5h 16m
ORD11:56 pmChicago O'Hare Intl
$221
Find similar
Spirit Airlines
Aug 31
ORD5:05 amChicago O'Hare Intl
15h 43m
1 stop
SJU9:48 pmSan Juan Luis Munoz Marin Intl
Sep 5
SJU3:19 pmSan Juan Luis Munoz Marin Intl
7h 39m
1 stop
ORD9:58 pmChicago O'Hare Intl
$226
Find similar

Frontier flights from Illinois to Caribbean

Our best Frontier deals on Illinois to Caribbean flight tickets
Frontier
Oct 11
ORD6:40 amChicago O'Hare Intl
7h 44m
1 stop
SJU3:24 pmSan Juan Luis Munoz Marin Intl
Oct 17
SJU3:40 amSan Juan Luis Munoz Marin Intl
12h 59m
1 stop
ORD3:39 pmChicago O'Hare Intl
$216
Find similar
Frontier
Oct 18
MDW11:31 amChicago Midway
13h 59m
1 stop
SJU2:30 amSan Juan Luis Munoz Marin Intl
Oct 25
SJU4:18 pmSan Juan Luis Munoz Marin Intl
8h 07m
1 stop
MDW11:25 pmChicago Midway
$221
Find similar
Frontier
Oct 25
MDW11:31 amChicago Midway
13h 59m
1 stop
SJU2:30 amSan Juan Luis Munoz Marin Intl
Oct 31
SJU3:31 pmSan Juan Luis Munoz Marin Intl
7h 37m
1 stop
MDW10:08 pmChicago Midway
$222
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Caribbean 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 August 21, 2025.
Use the filters below to find and compare flights from Illinois to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 10/11

6:40 am-3:24 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

Fri 10/17

3:40 am-3:39 pm

1 stop12h 59m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/31

5:05 am-9:48 pm

1 stop15h 43m

San Juan Luis Munoz Marin Intl

Fri 9/5

7:40 pm-11:56 pm

Nonstop5h 16m

$220

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 9/20

8:56 pm-2:17 pm

1 stop16h 21m

San Juan Luis Munoz Marin Intl

Fri 9/26

3:39 am-3:17 pm

1 stop12h 38m

$228

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 9/17

6:30 am-2:11 pm

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Fri 9/19

3:39 am-3:17 pm

1 stop12h 38m

$233

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 9/2

8:35 am-2:05 pm

Nonstop4h 30m

Punta Cana

Tue 9/9

4:25 pm-11:12 pm

1 stop7h 47m

$338

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 10/5

6:25 am-2:20 pm

1 stop6h 55m

Punta Cana

Fri 10/10

3:30 pm-10:20 pm

1 stop7h 50m

$343

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 10/6

8:35 am-2:00 pm

Nonstop4h 25m

Punta Cana

Fri 10/10

3:21 pm-7:36 pm

Nonstop5h 15m

$346

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 9/23

6:00 am-2:32 pm

1 stop7h 32m

Punta Cana

Fri 9/26

1:57 pm-9:48 am

2 stops20h 51m

$347

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 10/27

5:20 am-1:24 pm

1 stop7h 04m

Punta Cana

Tue 10/28

1:53 pm-7:50 am

2 stops18h 57m

$347

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 10/24

7:05 am-2:30 pm

1 stop6h 25m

Punta Cana

Wed 10/29

1:40 pm-10:35 pm

1 stop9h 55m

$368

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Illinois to Caribbean

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?

In general, September is the cheapest month to fly from Illinois to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $305. If you don’t want to visit Caribbean in September, then you should wait until October to fly from Illinois, when ticket prices are also cheap, with an average price of $309.

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

The cheapest day to depart from Illinois to Caribbean is on a Monday when prices can be found for as low as $392. If your travel schedule is flexible, try to avoid departing on a Sunday 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.

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

In the evening is the cheapest time of day to fly from Illinois to Caribbean when you can find flight prices for as low as $306. Flying to Caribbean in the evening is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $444.

What is the cheapest Illinois to Caribbean flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Illinois - Caribbean flight prices

How far in advance should I book a flight to Caribbean?

You are more likely to see cheaper flights to Caribbean from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $383 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Illinois for as low as $306 on momondo.

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

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

You could potentially save up to 1% on your flight if you consider stops on a Illinois to Caribbean flight.

Cheap Illinois to Caribbean flight deals and tips

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

Best Price Found

$126

Fastest flight time

3h 18m

Direct flights

Every day

Airports in Caribbean

3 airports
The best one-way flight to Caribbean from Illinois in the past 72 hours is $126. The best round-trip flight deal from Illinois to Caribbean found on momondo in the last 72 hours is $282.
The fastest flight from Illinois to Caribbean takes 3h 18m
Direct flights go from Illinois to Caribbean every day.
There are 3 airports near Caribbean: Nassau Intl (NAS), Montego Bay Sangster Intl (MBJ), Providenciales (PLS)
Search flight deals

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

    Prices for flights from Illinois to Caribbean were last updated today.

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

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

    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 Illinois to Caribbean.

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

    The necessary travel and health documents for your Caribbean 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?

Best airlines flying from Illinois to Caribbean

Compare and see reviews for airlines that fly from Illinois to Caribbean with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $106Free CancellationRating
5.8
3,207 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,035 reviews
Search Spirit Airlines flights
DeltaPriceFrom $190Free CancellationRating
7.9
7,981 reviews
Search Delta flights
Copa AirlinesPriceFrom $193Free CancellationRating
7.5
1,512 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $194Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,930 reviews
Search United Airlines flights
ArajetPriceFrom $234Free CancellationRating
7.0
34 reviews
Search Arajet flights
JetBluePriceFrom $261Free CancellationRating
7.2
2,916 reviews
Search JetBlue flights
Air CanadaPriceFrom $335Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Illinois to Caribbean. momondo saves you time and could save you money on your trip.

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

momondo does allow users to show only those flights to Caribbean from Illinois which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Illinois to Caribbean?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Illinois to Caribbean.

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

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

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Find better results for your trip to Caribbean

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