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Cheap flights from Illinois to Caribbean Islands from $85

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 12/7. 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 Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:45 am - 12:26 pmORD-SJU
4h 41mnonstop
Multiple Airlines Logo
9:37 pm - 2:29 pmSJU-ORD
18h 52m1 stop
$213Multiple Airlines
Find Deal
dom., ene. 4 - mié., ene. 14
Multiple Airlines Logo
5:01 am - 2:57 pmORD-SJU
7h 56m1 stop
Multiple Airlines Logo
4:40 pm - 11:47 amSJU-ORD
21h 07m2 stops
$214Multiple Airlines
Find Deal
dom., ene. 11 - mié., ene. 14
Frontier Logo
6:11 pm - 10:17 amORD-SJU
14h 06m1 stop
Frontier Logo
2:29 am - 2:13 pmSJU-ORD
13h 44m1 stop
$216Frontier
Find Deal
sáb., ene. 10 - sáb., ene. 17
Frontier Logo
2:16 pm - 10:32 amMDW-SJU
18h 16m1 stop
Frontier Logo
4:21 pm - 10:12 pmSJU-MDW
7h 51m1 stop
$216Frontier
Find Deal
jue., dic. 11 - jue., dic. 18
Spirit Airlines Logo
5:45 am - 12:26 pmORD-SJU
4h 41mnonstop
Spirit Airlines Logo
1:22 pm - 4:37 pmSJU-ORD
5h 15mnonstop
$217Spirit Airlines
Find Deal
mié., ene. 7 - sáb., ene. 17
Spirit Airlines Logo
12:22 pm - 6:54 pmORD-SJU
4h 32mnonstop
Spirit Airlines Logo
1:22 pm - 4:37 pmSJU-ORD
5h 15mnonstop
$218Spirit Airlines
Find Deal
jue., ene. 8 - sáb., ene. 17
American Airlines Logo
7:30 pm - 10:48 amORD-SJU
13h 18m1 stop
American Airlines Logo
6:00 am - 9:35 amSJU-ORD
5h 35mnonstop
$221American Airlines
Find Deal
sáb., ene. 17 - sáb., ene. 24
United Airlines Logo
2:20 pm - 9:00 pmORD-SJU
4h 40mnonstop
United Airlines Logo
2:05 am - 9:40 amSJU-ORD
9h 35m1 stop
$222United Airlines
Find Deal
mar., ene. 20 - lun., ene. 26
American Airlines Logo
3:15 pm - 9:54 pmORD-SJU
4h 39mnonstop
American Airlines Logo
6:00 am - 9:35 amSJU-ORD
5h 35mnonstop
$241American Airlines
Find Deal
dom., ene. 18 - sáb., ene. 31
United Airlines Logo
8:45 am - 5:25 pmORD-PUJ
6h 40m1 stop
United Airlines Logo
2:55 pm - 6:08 pmPUJ-ORD
5h 13mnonstop
$268United Airlines
Find Deal
mar., dic. 2 - vie., dic. 5

Frontier flights from Illinois to Caribbean Islands

Our best Frontier deals on Illinois to Caribbean Islands flight tickets
Frontier
Jan 10
ORD6:11 pmChicago O'Hare Intl
14h 06m
1 stop
SJU10:17 amSan Juan Luis Munoz Marin Intl
Jan 17
SJU2:29 amSan Juan Luis Munoz Marin Intl
13h 44m
1 stop
ORD2:13 pmChicago O'Hare Intl
$216
Find similar
Frontier
Dec 7
MDW7:44 amChicago Midway
30h 29m
1 stop
SJU4:13 pmSan Juan Luis Munoz Marin Intl
Dec 13
SJU1:59 amSan Juan Luis Munoz Marin Intl
35h 09m
2 stops
MDW11:08 amChicago Midway
$221
Find similar
Frontier
Jan 4
ORD5:05 amChicago O'Hare Intl
7h 52m
1 stop
SJU2:57 pmSan Juan Luis Munoz Marin Intl
Jan 11
SJU2:29 amSan Juan Luis Munoz Marin Intl
13h 41m
1 stop
ORD2:10 pmChicago O'Hare Intl
$223
Find similar

Spirit Airlines flights from Illinois to Caribbean Islands

Our best Spirit Airlines deals on Illinois to Caribbean Islands flight tickets
Spirit Airlines
Jan 7
ORD5:45 amChicago O'Hare Intl
4h 41m
SJU12:26 pmSan Juan Luis Munoz Marin Intl
Jan 17
SJU1:22 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD4:37 pmChicago O'Hare Intl
$217
Find similar
Spirit Airlines
Jan 8
ORD12:22 pmChicago O'Hare Intl
4h 32m
SJU6:54 pmSan Juan Luis Munoz Marin Intl
Jan 17
SJU1:22 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD4:37 pmChicago O'Hare Intl
$218
Find similar
Spirit Airlines
Nov 24
ORD5:00 amChicago O'Hare Intl
13h 27m
1 stop
SJU8:27 pmSan Juan Luis Munoz Marin Intl
Nov 27
SJU11:55 amSan Juan Luis Munoz Marin Intl
13h 18m
1 stop
ORD11:13 pmChicago O'Hare Intl
$220
Find similar

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 noviembre 10, 2025.
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

dom. 1/4

5:45 am-12:26 pm

Nonstop4h 41m

San Juan Luis Munoz Marin Intl

mié. 1/14

9:37 pm-2:29 pm

1 stop18h 52m

$213

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

dom. 1/11

5:01 am-2:57 pm

1 stop7h 56m

San Juan Luis Munoz Marin Intl

mié. 1/14

4:40 pm-11:47 am

2 stops21h 07m

$214

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 1/10

6:11 pm-10:17 am

1 stop14h 06m

San Juan Luis Munoz Marin Intl

sáb. 1/17

2:29 am-2:13 pm

1 stop13h 44m

$216

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

jue. 12/11

2:16 pm-10:32 am

1 stop18h 16m

San Juan Luis Munoz Marin Intl

jue. 12/18

4:21 pm-10:12 pm

1 stop7h 51m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 1/7

5:45 am-12:26 pm

Nonstop4h 41m

San Juan Luis Munoz Marin Intl

sáb. 1/17

1:22 pm-4:37 pm

Nonstop5h 15m

$217

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

jue. 1/8

12:22 pm-6:54 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

sáb. 1/17

1:22 pm-4:37 pm

Nonstop5h 15m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 1/17

7:30 pm-10:48 am

1 stop13h 18m

San Juan Luis Munoz Marin Intl

sáb. 1/24

6:00 am-9:35 am

Nonstop5h 35m

$221

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 1/20

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

lun. 1/26

2:05 am-9:40 am

1 stop9h 35m

$222

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

dom. 1/18

3:15 pm-9:54 pm

Nonstop4h 39m

San Juan Luis Munoz Marin Intl

sáb. 1/31

6:00 am-9:35 am

Nonstop5h 35m

$241

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 12/2

8:45 am-5:25 pm

1 stop6h 40m

Punta Cana

vie. 12/5

2:55 pm-6:08 pm

Nonstop5h 13m

$268

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 $352. The month of May is another great option to travel to Caribbean Islands, with average flight prices from Illinois averaging around $352.

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 Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $393. If your travel schedule is flexible, try to avoid departing on a Thursday 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 Illinois to Caribbean Islands in the evening for as low as $314. 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 $450. 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 Punta Cana 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 $392 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 $335 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 18m

Direct flights

Every day

Airports in Caribbean Islands

4 airports
The fastest flight from Illinois to Caribbean Islands takes 3h 18m
Direct flights go from Illinois to Caribbean Islands every day.
There are 4 airports near Caribbean Islands: George Town Owen Roberts Intl (GCM), 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 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
5.8
3,114 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,136 reviews
Search Spirit Airlines flights
DeltaPriceFrom $186Free CancellationRating
7.9
8,006 reviews
Search Delta flights
Copa AirlinesPriceFrom $188Free CancellationRating
7.6
1,562 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $225Free CancellationRating
7.2
11,045 reviews
Search American Airlines flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
9,012 reviews
Search United Airlines flights
ArajetPriceFrom $233Free CancellationRating
7.1
36 reviews
Search Arajet flights
JetBluePriceFrom $261Free CancellationRating
7.2
2,907 reviews
Search JetBlue flights
Air CanadaPriceFrom $335Free CancellationRating
7.1
10,437 reviews
Search Air Canada 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

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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1 adult
mié. 12/10
mié. 12/17
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