What airlines fly to Caribbean?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Caribbean from Illinois according to our data. American Airlines is the first choice among our users, with 36% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 12 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

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

183 flights are operational weekly from Illinois to Caribbean as of December 2025. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.

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

26 flights are operational daily from Illinois to Caribbean as of December 2025. The most popular departure time for this route is 8:00AM, with 74% of flights per day taking off at noon.

How long is the flight from Illinois to Caribbean?

If you’re flying from a popular airport in Illinois, such as Chicago or Moline, and flying into Caribbean, then you can expect flight times to average 17h 25m and 22h 28m, respectively.

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

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

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?

There are 11 operators available for flights from Illinois to Caribbean as of December 2025.

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.

$72 Cheap Flights from Illinois to Caribbean in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Illinois to Caribbean

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:18 am - 7:43 pm

ORD

SJU

8h 25m1 stop

5:25 pm - 11:15 pm

SJU

ORD

7h 50m1 stop

$195Multiple Airlines

Sat, Feb 21 - Mon, Mar 2

6:00 am - 3:06 pm

MDW

SJU

7h 06m1 stop

5:25 pm - 1:08 pm

SJU

MDW

21h 43m1 stop

$195Frontier

Tue, Mar 3 - Thu, Mar 5

7:45 am - 6:05 pm

ORD

SJU

8h 20m1 stop

11:06 am - 7:36 pm

SJU

ORD

10h 30m1 stop

$196JetBlue

Tue, Jan 13 - Fri, Jan 23

12:17 pm - 6:49 pm

ORD

SJU

4h 32mnonstop

1:22 pm - 4:37 pm

SJU

ORD

5h 15mnonstop

$197Spirit Airlines

Sat, Jan 24 - Wed, Feb 4

12:41 pm - 11:44 pm

ORD

SJU

9h 03m1 stop

5:10 am - 11:48 am

SJU

ORD

8h 38m1 stop

$202JetBlue

Fri, Feb 27 - Mon, Mar 2

5:15 am - 1:38 pm

ORD

GCM

7h 23m1 stop

2:34 pm - 11:46 pm

GCM

ORD

10h 12m1 stop

$240Spirit Airlines

Sat, Jan 10 - Sat, Jan 17

5:45 am - 12:30 pm

ORD

PUJ

4h 45mnonstop

6:00 pm - 9:10 pm

PUJ

ORD

5h 10mnonstop

$249Arajet

Wed, Feb 25 - Sun, Mar 1

10:27 am - 5:12 pm

ORD

PUJ

4h 45mnonstop

5:47 am - 8:57 am

PUJ

ORD

5h 10mnonstop

$251Arajet

Sat, Feb 21 - Sat, Feb 28

12:50 pm - 12:15 pm

ORD

NAS

22h 25m1 stop

11:15 am - 11:43 am

NAS

ORD

25h 28m1 stop

$356Air Canada

Sat, Mar 28 - Fri, Apr 3

6:04 pm - 12:15 pm

ORD

NAS

17h 11m2 stops

1:25 pm - 8:00 am

NAS

ORD

19h 35m2 stops

$359Air Canada

Sat, Mar 28 - Fri, Apr 3

Frontier flights from Illinois to Caribbean

Our best Frontier deals on Illinois to Caribbean flight tickets

Frontier

Mar 3

MDW6:00 amChicago Midway

7h 06m

1 stop

SJU3:06 pmSan Juan Luis Munoz Marin Intl

Mar 5

SJU5:25 pmSan Juan Luis Munoz Marin Intl

21h 43m

1 stop

MDW1:08 pmChicago Midway

$195

Find similar

Frontier

Mar 3

MDW6:00 amChicago Midway

7h 06m

1 stop

SJU3:06 pmSan Juan Luis Munoz Marin Intl

Mar 10

SJU6:30 amSan Juan Luis Munoz Marin Intl

12h 43m

1 stop

MDW6:13 pmChicago Midway

$196

Find similar

Frontier

Feb 14

MDW8:00 amChicago Midway

27h 27m

1 stop

SJU1:27 pmSan Juan Luis Munoz Marin Intl

Feb 18

SJU5:25 pmSan Juan Luis Munoz Marin Intl

23h 01m

1 stop

MDW2:26 pmChicago Midway

$197

Find similar

Southwest flights from Illinois to Caribbean

Our best Southwest deals on Illinois to Caribbean flight tickets

Southwest

Jan 21

MDW1:50 pmChicago Midway

8h 45m

2 stops

SJU12:35 amSan Juan Luis Munoz Marin Intl

Jan 28

SJU5:40 amSan Juan Luis Munoz Marin Intl

7h 35m

1 stop

MDW11:15 amChicago Midway

$245

Find similar

Southwest

Mar 6

MDW9:15 amChicago Midway

4h 15m

PUJ3:30 pmPunta Cana

Mar 11

PUJ2:35 pmPunta Cana

5h 05m

MDW6:40 pmChicago Midway

$383

Find similar

Southwest

Jan 31

MDW8:15 amChicago Midway

4h 20m

PUJ2:35 pmPunta Cana

Feb 5

PUJ3:30 pmPunta Cana

7h 55m

1 stop

MDW9:25 pmChicago Midway

$391

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

9:18 am-7:43 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Mon 3/2

5:25 pm-11:15 pm

1 stop7h 50m

$195

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 3/3

6:00 am-3:06 pm

1 stop7h 06m

San Juan Luis Munoz Marin Intl

Thu 3/5

5:25 pm-1:08 pm

1 stop21h 43m

$195

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 1/13

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Fri 1/23

11:06 am-7:36 pm

1 stop10h 30m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Wed 2/4

1:22 pm-4:37 pm

Nonstop5h 15m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/27

12:41 pm-11:44 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Mon 3/2

5:10 am-11:48 am

1 stop8h 38m

$202

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/10

5:15 am-1:38 pm

1 stop7h 23m

George Town Owen Roberts Intl

Sat 1/17

2:34 pm-11:46 pm

1 stop10h 12m

$240

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 2/25

5:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Sun 3/1

6:00 pm-9:10 pm

Nonstop5h 10m

$249

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 2/21

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 2/28

5:47 am-8:57 am

Nonstop5h 10m

$251

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Sat 3/28

12:50 pm-12:15 pm

1 stop22h 25m

Nassau Intl

Fri 4/3

11:15 am-11:43 am

1 stop25h 28m

$356

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Sat 3/28

6:04 pm-12:15 pm

2 stops17h 11m

Nassau Intl

Fri 4/3

1:25 pm-8:00 am

2 stops19h 35m

$359

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 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

Prices

Airlines

Other information

What is the cheapest month to fly to Caribbean?

In general, April 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 $349. If you don’t want to visit Caribbean in April, then you should wait until January to fly from Illinois, when ticket prices are also cheap, with an average price of $351.

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 $389. 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.

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 $321. 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 $447.

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 $395 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 $338 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 38% 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	$153
Fastest flight time	3h 22m
Direct flights	Every day
Airports in Caribbean	195 airports

The best one-way flight to Caribbean from Illinois in the past 72 hours is $153. The best round-trip flight deal from Illinois to Caribbean found on momondo in the last 72 hours is $315.

The fastest flight from Illinois to Caribbean takes 3h 22m

Direct flights go from Illinois to Caribbean every day.

There are 195 airports in Caribbean. From Illinois there are direct flights to 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?
Prices for flights from Illinois to Caribbean were last updated today.
How many operators does momondo search for flights from Illinois to Caribbean?
There are 11 operators available for flights from Illinois to Caribbean as of December 2025.
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?
Based on momondo bookings for flights between Illinois and Caribbean, the leading plane model is Boeing 737-800, making up 24.94% of the total bookings. Other popular models include Airbus A321neo with 21.85%, Boeing 737 MAX 8 with 16.01%, and Boeing 737-900 with 11.44%.

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
Frontier	PriceFrom $108	Free Cancellation	Rating 5.8 3,081 reviews	Search Frontier flights
JetBlue	PriceFrom $142	Free Cancellation	Rating 7.2 2,897 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom $145	Free Cancellation	Rating 6.3 8,190 reviews	Search Spirit Airlines flights
Delta	PriceFrom $186	Free Cancellation	Rating 7.9 8,005 reviews	Search Delta flights
Copa Airlines	PriceFrom $188	Free Cancellation	Rating 7.6 1,556 reviews	Search Copa Airlines flights
United Airlines	PriceFrom $215	Free Cancellation	Rating 7.4 9,091 reviews	Search United Airlines flights
American Airlines	PriceFrom $225	Free Cancellation	Rating 7.2 11,054 reviews	Search American Airlines flights
Arajet	PriceFrom $236	Free Cancellation	Rating 6.8 38 reviews	Search Arajet flights
Southwest	PriceFrom $277	Free Cancellation	Rating 7.9 4,250 reviews	Search Southwest 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.