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

Frontier, JetBlue, and United Airlines are the most popular carriers operating from Caribbean to Illinois

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

The number of flights available between Caribbean and Illinois is 21 per day as of December 2025. The most frequent departure time is 4:00PM, with 54% of daily flights leaving in the afternoon.

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

As of December 2025, 153 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.

What airlines fly to Illinois?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Illinois from Caribbean according to our data. American Airlines is the first choice among our users, with 33% of people opting to fly with this airline when traveling to Illinois. Keep in mind that there are 7 different airlines that fly to Illinois on a routine basis, so you have a few additional options to choose from.

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 7 as of December 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.

$84 Cheap Flights from Caribbean to Illinois in 2025/26

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Find the cheapest flights from Caribbean to Illinois

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

11:06 am - 7:36 pm

SJU

ORD

10h 30m1 stop

9:40 am - 7:23 pm

ORD

SJU

7h 43m1 stop

$162JetBlue

Thu, Jan 15 - Wed, Jan 21

8:00 am - 10:35 am

SJU

ORD

28h 35m1 stop

5:40 am - 3:12 pm

ORD

SJU

7h 32m1 stop

$163Frontier

Thu, Jan 22 - Mon, Jan 26

3:53 am - 3:52 pm

SJU

ORD

13h 59m1 stop

12:51 pm - 11:44 pm

ORD

SJU

8h 53m1 stop

$174Multiple Airlines

Mon, Feb 23 - Sat, Feb 28

1:22 pm - 4:37 pm

SJU

ORD

5h 15mnonstop

9:23 am - 6:58 pm

ORD

SJU

7h 35m1 stop

$176Spirit Airlines

Fri, Jan 23 - Mon, Jan 26

6:00 am - 7:27 am

SJU

MDW

27h 27m2 stops

8:19 pm - 12:42 pm

MDW

SJU

14h 23m1 stop

$198Multiple Airlines

Fri, Jan 16 - Sun, Jan 18

6:15 am - 12:06 pm

SJU

STL

6h 51m1 stop

11:43 am - 8:06 pm

STL

SJU

7h 23m1 stop

$225Delta

Thu, Apr 16 - Sun, Apr 19

6:00 am - 2:47 pm

SJU

STL

10h 47m2 stops

6:00 am - 4:30 pm

STL

SJU

8h 30m1 stop

$229American Airlines

Thu, Jan 15 - Mon, Jan 19

6:00 am - 2:47 pm

SJU

STL

10h 47m2 stops

6:00 am - 5:03 pm

STL

SJU

9h 03m2 stops

$230American Airlines

Thu, Jan 15 - Mon, Jan 19

5:47 pm - 11:47 pm

PUJ

ORD

8h 00m1 stop

5:15 am - 4:36 pm

ORD

PUJ

9h 21m1 stop

$232Spirit Airlines

Wed, Feb 4 - Wed, Feb 11

7:30 am - 5:45 pm

SDQ

MDW

12h 15m2 stops

6:00 am - 3:30 pm

MDW

SDQ

7h 30m1 stop

$453Delta

Thu, Feb 19 - Sat, Feb 21

Frontier flights from Caribbean to Illinois

Our best Frontier deals on Caribbean to Illinois flight tickets

Frontier

Jan 22

SJU8:00 amSan Juan Luis Munoz Marin Intl

28h 35m

1 stop

ORD10:35 amChicago O'Hare Intl

Jan 26

ORD5:40 amChicago O'Hare Intl

7h 32m

1 stop

SJU3:12 pmSan Juan Luis Munoz Marin Intl

$163

Find similar

Frontier

Feb 9

SJU3:53 amSan Juan Luis Munoz Marin Intl

13h 59m

1 stop

ORD3:52 pmChicago O'Hare Intl

Feb 14

ORD4:42 pmChicago O'Hare Intl

7h 15m

1 stop

SJU1:57 amSan Juan Luis Munoz Marin Intl

$176

Find similar

Frontier

Jan 8

SJU6:00 amSan Juan Luis Munoz Marin Intl

17h 31m

1 stop

ORD9:31 pmChicago O'Hare Intl

Jan 12

ORD5:50 amChicago O'Hare Intl

7h 29m

1 stop

SJU3:19 pmSan Juan Luis Munoz Marin Intl

$180

Find similar

JetBlue flights from Caribbean to Illinois

Our best JetBlue deals on Caribbean to Illinois flight tickets

JetBlue

Jan 15

SJU11:06 amSan Juan Luis Munoz Marin Intl

10h 30m

1 stop

ORD7:36 pmChicago O'Hare Intl

Jan 21

ORD9:40 amChicago O'Hare Intl

7h 43m

1 stop

SJU7:23 pmSan Juan Luis Munoz Marin Intl

$162

Find similar

JetBlue

Jan 23

SJU11:06 amSan Juan Luis Munoz Marin Intl

10h 30m

1 stop

ORD7:36 pmChicago O'Hare Intl

Jan 26

ORD9:40 amChicago O'Hare Intl

7h 46m

1 stop

SJU7:26 pmSan Juan Luis Munoz Marin Intl

$165

Find similar

JetBlue

Mar 4

SJU1:44 pmSan Juan Luis Munoz Marin Intl

11h 10m

1 stop

ORD10:54 pmChicago O'Hare Intl

Mar 8

ORD12:41 pmChicago O'Hare Intl

7h 50m

1 stop

SJU9:31 pmSan Juan Luis Munoz Marin Intl

$169

Find similar

Fly from

Fly to

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/15

11:06 am-7:36 pm

1 stop10h 30m

Chicago O'Hare Intl

Wed 1/21

9:40 am-7:23 pm

1 stop7h 43m

$162

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/22

8:00 am-10:35 am

1 stop28h 35m

Chicago O'Hare Intl

Mon 1/26

5:40 am-3:12 pm

1 stop7h 32m

$163

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 2/23

3:53 am-3:52 pm

1 stop13h 59m

Chicago O'Hare Intl

Sat 2/28

12:51 pm-11:44 pm

1 stop8h 53m

$174

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 1/23

1:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Mon 1/26

9:23 am-6:58 pm

1 stop7h 35m

$176

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/16

6:00 am-7:27 am

2 stops27h 27m

Chicago Midway

Sun 1/18

8:19 pm-12:42 pm

1 stop14h 23m

$198

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Thu 4/16

6:15 am-12:06 pm

1 stop6h 51m

Lambert-St Louis

Sun 4/19

11:43 am-8:06 pm

1 stop7h 23m

$225

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Thu 1/15

6:00 am-2:47 pm

2 stops10h 47m

Lambert-St Louis

Mon 1/19

6:00 am-4:30 pm

1 stop8h 30m

$229

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Thu 1/15

6:00 am-2:47 pm

2 stops10h 47m

Lambert-St Louis

Mon 1/19

6:00 am-5:03 pm

2 stops9h 03m

$230

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 2/4

5:47 pm-11:47 pm

1 stop8h 00m

Chicago O'Hare Intl

Wed 2/11

5:15 am-4:36 pm

1 stop9h 21m

$232

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/19

7:30 am-5:45 pm

2 stops12h 15m

Chicago Midway

Sat 2/21

6:00 am-3:30 pm

1 stop7h 30m

$453

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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 February. Flight prices, which tend to average around $260, 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 February, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $269.

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 $384. Flights from Caribbean to Illinois on a Sunday will generally be more expensive and average around $544. 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 $257. Flights in the afternoon are often more expensive with an average ticket price of $477.

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 $336 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 $286 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.

Can stopping save me money on Caribbean to Illinois flights?

You could potentially save up to 10% on your flight if you consider stops on a Caribbean to Illinois flight.

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	$166
Fastest flight time	3h 56m
Direct flights	Every day
Airports in Illinois	98 airports

The best one-way flight to Illinois from Caribbean in the past 72 hours is $166. The best round-trip flight deal from Caribbean to Illinois found on momondo in the last 72 hours is $195.

The fastest flight from Caribbean to Illinois takes 3h 56m

Direct flights go from Caribbean to Illinois every day.

There are 98 airports in Illinois. From Caribbean there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

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 7 as of December 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 40.16% of all bookings. The subsequent popular models are Boeing 737-800 at 9.09%, Airbus A320-100/200 at 8.72%, and Boeing 737 MAX 8 at 8.20%.

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
JetBlue	PriceFrom $120	Free Cancellation	Rating 7.2 2,897 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom $138	Free Cancellation	Rating 6.3 8,203 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $138	Free Cancellation	Rating 5.7 3,069 reviews	Search Frontier flights
Delta	PriceFrom $162	Free Cancellation	Rating 7.9 8,011 reviews	Search Delta flights
American Airlines	PriceFrom $258	Free Cancellation	Rating 7.2 11,056 reviews	Search American Airlines flights
United Airlines	PriceFrom $271	Free Cancellation	Rating 7.4 9,114 reviews	Search United Airlines flights
Southwest	PriceFrom $392	Free Cancellation	Rating 8.0 4,258 reviews	Search Southwest 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.