What is the cheapest airline that flies from Caribbean to Illinois?

Spirit Airlines, United Airlines, and American Airlines are the most popular carriers operating from Caribbean to Illinois

What airlines fly to Illinois?

Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to Illinois from Caribbean according to our data. Spirit Airlines is the first choice among our users, with 35% of people opting to fly with this airline when traveling to Illinois. Keep in mind that there are 6 different airlines that fly to Illinois on a routine basis, so you have a few additional options to choose from.

How many flights depart from Caribbean to Illinois on average per day?

The number of flights available between Caribbean and Illinois is 16 per day as of July 2025. The most frequent departure time is 3:00PM, with 71% of daily flights leaving in the afternoon.

How many flights depart from Caribbean to Illinois on average per week?

As of July 2025, 115 flights take off from Caribbean and land in Illinois each week. The most common flight departure day for this route is Wed, with 16% of weekly flights taking off on this day.

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

Prices for flights from Caribbean to Illinois are refreshed on a daily basis.

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

The number of operators available for flights from Caribbean to Illinois is 6 as of July 2025.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Caribbean to Illinois.

What documentation or ID do you need to fly to Illinois?

The necessary travel and health documents for your Illinois 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.

$99 Cheap Flights from Caribbean to Illinois in 2025

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Find the cheapest flights from Caribbean to Illinois

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

4:43 pm - 7:04 amSJU-ORD

15h 21m1 stop

6:56 am - 11:57 pmORD-SJU

16h 01m1 stop

$200Spirit Airlines

Find Deal

Tue, Aug 5 - Tue, Aug 19

10:14 pm - 8:55 amSJU-ORD

11h 41m1 stop

5:05 am - 9:09 pmORD-SJU

15h 04m1 stop

$203Spirit Airlines

Find Deal

Thu, Aug 7 - Sun, Aug 10

5:00 pm - 11:47 pmSJU-STL

7h 47m1 stop

5:40 pm - 2:39 amSTL-SJU

7h 59m1 stop

$250Frontier

Find Deal

Fri, Aug 1 - Tue, Aug 12

12:59 am - 12:20 pmSJU-ORD

12h 21m1 stop

5:10 am - 2:26 pmORD-SJU

8h 16m1 stop

$257Frontier

Find Deal

Wed, Aug 27 - Sun, Aug 31

6:00 am - 4:14 pmSJU-STL

11h 14m2 stops

7:32 am - 11:10 pmSTL-SJU

14h 38m1 stop

$340American Airlines

Find Deal

Tue, Aug 26 - Sun, Aug 31

2:38 pm - 10:26 pmMBJ-ORD

7h 48m1 stop

8:40 am - 12:41 pmORD-MBJ

4h 01mnonstop

$344American Airlines

Find Deal

Fri, Oct 3 - Tue, Oct 7

1:10 pm - 9:26 pmPUJ-MDW

9h 16m1 stop

6:00 am - 1:20 pmMDW-PUJ

6h 20m1 stop

$350Delta

Find Deal

Fri, Sep 5 - Sun, Sep 14

2:40 pm - 10:37 pmPUJ-ORD

8h 57m1 stop

5:30 am - 1:20 pmORD-PUJ

6h 50m1 stop

$350Delta

Find Deal

Fri, Sep 5 - Sun, Sep 14

1:51 pm - 6:20 pmMBJ-ORD

4h 29mnonstop

9:50 pm - 1:30 pmORD-MBJ

15h 40m1 stop

$423United Airlines

Find Deal

Fri, Aug 1 - Sat, Aug 2

1:51 pm - 6:20 pmMBJ-ORD

4h 29mnonstop

8:52 am - 3:10 pmORD-MBJ

6h 18m1 stop

$451United Airlines

Find Deal

Fri, Aug 1 - Sun, Aug 3

Spirit Airlines flights from Caribbean to Illinois

Our best Spirit Airlines deals on Caribbean to Illinois flight tickets

Spirit Airlines

Aug 5

SJU4:43 pmSan Juan Luis Munoz Marin Intl

15h 21m

1 stop

ORD7:04 amChicago O'Hare Intl

Aug 19

ORD6:56 amChicago O'Hare Intl

16h 01m

1 stop

SJU11:57 pmSan Juan Luis Munoz Marin Intl

$200

Find similar

Spirit Airlines

Aug 7

SJU10:14 pmSan Juan Luis Munoz Marin Intl

11h 41m

1 stop

ORD8:55 amChicago O'Hare Intl

Aug 10

ORD5:05 amChicago O'Hare Intl

15h 04m

1 stop

SJU9:09 pmSan Juan Luis Munoz Marin Intl

$203

Find similar

Spirit Airlines

Aug 8

SJU3:50 pmSan Juan Luis Munoz Marin Intl

16h 14m

1 stop

ORD7:04 amChicago O'Hare Intl

Aug 11

ORD6:23 pmChicago O'Hare Intl

4h 43m

SJU12:06 amSan Juan Luis Munoz Marin Intl

$209

Find similar

United Airlines flights from Caribbean to Illinois

Our best United Airlines deals on Caribbean to Illinois flight tickets

United Airlines

Aug 1

MBJ1:51 pmMontego Bay Sangster Intl

4h 29m

ORD6:20 pmChicago O'Hare Intl

Aug 2

ORD9:50 pmChicago O'Hare Intl

15h 40m

1 stop

MBJ1:30 pmMontego Bay Sangster Intl

$423

Find similar

United Airlines

Aug 1

MBJ1:51 pmMontego Bay Sangster Intl

4h 29m

ORD6:20 pmChicago O'Hare Intl

Aug 3

ORD8:52 amChicago O'Hare Intl

6h 18m

1 stop

MBJ3:10 pmMontego Bay Sangster Intl

$451

Find similar

United Airlines

Jul 24

MBJ4:12 pmMontego Bay Sangster Intl

15h 37m

1 stop

ORD7:49 amChicago O'Hare Intl

Aug 4

ORD9:31 pmChicago O'Hare Intl

17h 39m

1 stop

MBJ3:10 pmMontego Bay Sangster Intl

$488

Find similar

How to get the cheapest flight ticket from Caribbean to Illinois

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

Prices

Airlines

Other information

What is the cheapest month to fly to Illinois?

The cheapest month to fly to Illinois from Caribbean is in January. Flight prices, which tend to average around $232, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of January, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $270.

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

The cheapest day to depart from Caribbean to Illinois is on a Friday when prices can be found for as low as $342. Flights from Caribbean to Illinois on a Monday will generally be more expensive and average around $478. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our most recent data shows that the best time of day to fly to Illinois is in the evening. Flights from Caribbean to Illinois during this time can be as low as $242. Flights at noon are often more expensive with an average ticket price of $482.

What is the cheapest Caribbean to Illinois flight route?

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

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

You are more likely to see cheaper flights to Illinois from Caribbean when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $318 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Caribbean for as low as $252 on momondo.

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

There are 4 cabin classes available to choose from on Caribbean to Illinois flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Caribbean to Illinois flight deals and tips

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

Best Price Found	$57
Fastest flight time	4h 28m
Direct flights	Every day
Airports in Illinois	3 airports

The best one-way flight to Illinois from Caribbean in the past 72 hours is $57. The best round-trip flight deal from Caribbean to Illinois found on momondo in the last 72 hours is $200.

The fastest flight from Caribbean to Illinois takes 4h 28m

Direct flights go from Caribbean to Illinois every day.

There are 3 airports near Illinois: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Lambert-St Louis (STL)

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When did momondo last update prices for flights from Caribbean to Illinois?
Prices for flights from Caribbean to Illinois are refreshed on a daily basis.
How many operators does momondo search for flights from Caribbean to Illinois?
The number of operators available for flights from Caribbean to Illinois is 6 as of July 2025.
How old do you have to be to fly from Caribbean to Illinois?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Caribbean to Illinois.
What documentation or ID do you need to fly to Illinois?
The necessary travel and health documents for your Illinois 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 Caribbean to Illinois?
momondo data reveals that the most frequently booked plane model on the route from Caribbean to Illinois is Airbus A321neo, representing 32.16% of all bookings. The subsequent popular models are Boeing 737 MAX 9 at 22.27%, Airbus A320neo at 11.29%, and Airbus A321-100/200 at 9.26%.

Best airlines flying from Caribbean to Illinois

Compare and see reviews for airlines that fly from Caribbean to Illinois with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $130	Free Cancellation	Rating 5.9 3,243 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $136	Free Cancellation	Rating 6.3 8,035 reviews	Search Spirit Airlines flights
Delta	PriceFrom $162	Free Cancellation	Rating 8.0 7,964 reviews	Search Delta flights
United Airlines	PriceFrom $218	Free Cancellation	Rating 7.4 8,871 reviews	Search United Airlines flights
Southwest	PriceFrom $257	Free Cancellation	Rating 8.0 4,232 reviews	Search Southwest flights
American Airlines	PriceFrom $329	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Caribbean to Illinois for you.

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

Yes. momondo enables you to select and highlight flights to Illinois from Caribbean with this policy.

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

momondo provides multiple filters to help you find the best flight to Illinois from Caribbean. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Illinois, momondo offers a useful price alert feature which will track prices for flights to Illinois from Caribbean and alert you when they change.