What airlines fly to Caribbean Islands?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Caribbean Islands from Illinois according to our data. American Airlines is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 11 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

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

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

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

As of July 2025, there are 14 flights per day flying from Illinois to Caribbean Islands. The most common time of day flights depart is 8:00AM, with 77% of flights taking off at noon.

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

As of July 2025, there are 101 flights per week flying from Illinois to Caribbean Islands. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.

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?

The number of operators available for flights from Illinois to Caribbean Islands is 11 as of July 2025.

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.

$87 Cheap Flights from Illinois to Caribbean Islands in 2025

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Find the cheapest flights from Illinois to Caribbean Islands

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:10 am - 11:51 amORD-SJU

4h 41mnonstop

12:06 pm - 10:48 pmSJU-ORD

11h 42m1 stop

$203Spirit Airlines

Find Deal

Wed, Sep 3 - Thu, Sep 11

10:00 am - 1:35 amORD-SJU

14h 35m1 stop

3:50 pm - 7:04 amSJU-ORD

16h 14m1 stop

$204Spirit Airlines

Find Deal

Sun, Aug 3 - Fri, Aug 8

6:20 am - 2:18 pmMDW-SJU

6h 58m1 stop

3:21 pm - 11:27 pmSJU-MDW

9h 06m1 stop

$220Frontier

Find Deal

Mon, Aug 18 - Fri, Aug 22

7:45 am - 4:43 pmORD-SJU

7h 58m1 stop

7:25 am - 6:28 pmSJU-ORD

12h 03m1 stop

$225Frontier

Find Deal

Mon, Aug 11 - Thu, Aug 21

5:30 am - 4:31 pmORD-SJU

10h 01m1 stop

7:30 am - 2:13 pmSJU-ORD

7h 43m1 stop

$233Delta

Find Deal

Wed, Oct 1 - Sat, Oct 18

10:35 am - 10:00 pmMDW-SJU

10h 25m1 stop

12:58 pm - 9:36 pmSJU-MDW

9h 38m1 stop

$233Delta

Find Deal

Tue, Sep 16 - Fri, Sep 19

5:05 am - 9:09 pmORD-SJU

15h 04m1 stop

3:29 am - 3:27 pmSJU-ORD

12h 58m1 stop

$234

Find Deal

Mon, Aug 11 - Wed, Aug 13

10:27 am - 5:12 pmORD-PUJ

4h 45mnonstop

5:47 am - 8:57 amPUJ-ORD

5h 10mnonstop

$242Arajet

Find Deal

Sat, Nov 29 - Sat, Dec 6

4:35 am - 11:20 amORD-PUJ

4h 45mnonstop

6:00 pm - 9:10 pmPUJ-ORD

5h 10mnonstop

$249Arajet

Find Deal

Tue, Nov 18 - Sun, Nov 23

10:26 am - 9:48 pmORD-SJU

10h 22m1 stop

3:21 pm - 11:33 pmSJU-ORD

9h 12m1 stop

$253

Find Deal

Mon, Aug 25 - Sat, Aug 30

Delta flights from Illinois to Caribbean Islands

Our best Delta deals on Illinois to Caribbean Islands flight tickets

Delta

Oct 1

ORD5:30 amChicago O'Hare Intl

10h 01m

1 stop

SJU4:31 pmSan Juan Luis Munoz Marin Intl

Oct 18

SJU7:30 amSan Juan Luis Munoz Marin Intl

7h 43m

1 stop

ORD2:13 pmChicago O'Hare Intl

$233

Find similar

Delta

Sep 8

MDW6:00 amChicago Midway

9h 36m

1 stop

SJU4:36 pmSan Juan Luis Munoz Marin Intl

Sep 12

SJU12:58 pmSan Juan Luis Munoz Marin Intl

9h 38m

1 stop

MDW9:36 pmChicago Midway

$243

Find similar

Delta

Nov 12

MDW10:35 amChicago Midway

10h 42m

1 stop

SJU11:17 pmSan Juan Luis Munoz Marin Intl

Nov 18

SJU3:30 pmSan Juan Luis Munoz Marin Intl

8h 14m

1 stop

MDW9:44 pmChicago Midway

$312

Find similar

Frontier flights from Illinois to Caribbean Islands

Our best Frontier deals on Illinois to Caribbean Islands flight tickets

Frontier

Aug 18

MDW6:20 amChicago Midway

6h 58m

1 stop

SJU2:18 pmSan Juan Luis Munoz Marin Intl

Aug 22

SJU3:21 pmSan Juan Luis Munoz Marin Intl

9h 06m

1 stop

MDW11:27 pmChicago Midway

$220

Find similar

Frontier

Aug 11

ORD7:45 amChicago O'Hare Intl

7h 58m

1 stop

SJU4:43 pmSan Juan Luis Munoz Marin Intl

Aug 21

SJU7:25 amSan Juan Luis Munoz Marin Intl

12h 03m

1 stop

ORD6:28 pmChicago O'Hare Intl

$225

Find similar

Frontier

Dec 6

MDW6:00 amChicago Midway

6h 54m

1 stop

SJU2:54 pmSan Juan Luis Munoz Marin Intl

Dec 14

SJU7:00 amSan Juan Luis Munoz Marin Intl

9h 05m

1 stop

MDW2:05 pmChicago Midway

$230

Find similar

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

Prices

Airlines

Other information

What is the cheapest month to fly to Caribbean Islands?

The month of September is, on average, the cheapest month to fly to Caribbean Islands from Illinois, with most prices found around $295. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Illinois averaging around $313.

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 Monday. Travelers who choose to depart for Caribbean Islands on a Monday will often find tickets for as low as $395. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $447. 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 $301. 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 $441. 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 Midway 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 $376 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 $302 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

Best Price Found	$87
Fastest flight time	4h 01m
Direct flights	Every day
Airports in Caribbean Islands	5 airports

The best one-way flight to Caribbean Islands from Illinois in the past 72 hours is $87. The best round-trip flight deal from Illinois to Caribbean Islands found on momondo in the last 72 hours is $203.

The fastest flight from Illinois to Caribbean Islands takes 4h 01m

Direct flights go from Illinois to Caribbean Islands every day.

There are 5 airports near Caribbean Islands: Saint Thomas Island Cyril E King (STT), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Providenciales (PLS), San Juan Luis Munoz Marin Intl (SJU)

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?
The number of operators available for flights from Illinois to Caribbean Islands is 11 as of July 2025.
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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Illinois to Caribbean Islands is Boeing 737-800 (17.24% of total bookings). The next most popular plane models are Airbus A321neo (9.15%), Boeing 737-900 (8.11%), and Airbus A321-100/200 (6.04%).

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
Frontier	PriceFrom $106	Free Cancellation	Rating 5.9 3,256 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $139	Free Cancellation	Rating 6.3 8,042 reviews	Search Spirit Airlines flights
Copa Airlines	PriceFrom $193	Free Cancellation	Rating 7.5 1,483 reviews	Search Copa Airlines flights
American Airlines	PriceFrom $194	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Delta	PriceFrom $216	Free Cancellation	Rating 8.0 7,957 reviews	Search Delta flights
United Airlines	PriceFrom $226	Free Cancellation	Rating 7.4 8,863 reviews	Search United Airlines flights
Arajet	PriceFrom $234	Free Cancellation	Rating 7.1 32 reviews	Search Arajet flights
JetBlue	PriceFrom $261	Free Cancellation	Rating 7.3 2,909 reviews	Search JetBlue flights
Air Canada	PriceFrom $335	Free Cancellation	Rating 7.1 9,734 reviews	Search Air Canada flights
Southwest	PriceFrom $352	Free Cancellation	Rating 8.0 4,241 reviews	Search Southwest 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

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Popular cities in Caribbean Islands

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Flights to Copenhagenfrom $355

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Flights to Manilafrom $497

Flights to Chicagofrom $48

Flights to Romefrom $292

Cheap flights from Illinois to Caribbean Islands from $87

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 8/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

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Find the cheapest flights from Illinois to Caribbean Islands

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Delta flights from Illinois to Caribbean Islands

Our best Delta deals on Illinois to Caribbean Islands flight tickets

Frontier flights from Illinois to Caribbean Islands

Our best Frontier deals on Illinois to Caribbean Islands flight tickets

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 September is, on average, the cheapest month to fly to Caribbean Islands from Illinois, with most prices found around $295. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Illinois averaging around $313.

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

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

What is the cheapest Illinois to Caribbean Islands flight route?

Fly from Chicago Midway to Punta Cana for the best Illinois - Caribbean Islands flight prices

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

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.

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

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

What airlines fly to Caribbean Islands?

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

As of July 2025, there are 14 flights per day flying from Illinois to Caribbean Islands. The most common time of day flights depart is 8:00AM, with 77% of flights taking off at noon.

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

As of July 2025, there are 101 flights per week flying from Illinois to Caribbean Islands. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.

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

Best Price Found

Fastest flight time

Direct flights

Airports in Caribbean Islands

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

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?

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

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

Why use momondo?

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

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

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

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

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

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