What is the cheapest airline that flies from Chicago Midway to Caribbean?

Southwest and Frontier are the most popular carriers operating from Chicago Midway to Caribbean

What airlines fly to Caribbean?

Southwest, Frontier and Delta are the top three most popular airlines that fly to Caribbean from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 68% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 5 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

How many operators does momondo search for flights from Chicago Midway Airport to Caribbean?

As of September 2025, there are 5 operators available to choose from for flights from Chicago Midway Airport to Caribbean.

How old do you have to be to fly from Chicago Midway Airport to Caribbean?

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 Chicago Midway Airport to Caribbean.

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

The travel and health documents you'll need for your trip to Caribbean may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$114 Cheap Flights from Chicago Midway Airport to Caribbean in 2025/26

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Find the cheapest flights from Chicago Midway Airport to Caribbean

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

5:50 pm - 9:50 amMDW-SJU

15h 00m2 stops

2:45 pm - 10:45 pmSJU-MDW

9h 00m1 stop

$227Southwest

Find Deal

Fri, Oct 17 - Tue, Oct 21

1:37 pm - 2:19 pmMDW-SJU

23h 42m1 stop

4:24 pm - 11:38 amSJU-MDW

21h 14m1 stop

$233Frontier

Find Deal

Thu, Oct 30 - Mon, Nov 3

9:15 am - 12:41 amMDW-SJU

13h 26m1 stop

2:11 am - 2:33 pmSJU-MDW

14h 22m1 stop

$237Frontier

Find Deal

Fri, Nov 14 - Sun, Nov 16

9:15 am - 12:29 amMDW-SJU

14h 14m1 stop

2:03 am - 2:33 pmSJU-MDW

14h 30m1 stop

$240Frontier

Find Deal

Thu, Oct 30 - Sun, Nov 2

8:25 am - 12:29 amMDW-SJU

15h 04m1 stop

1:59 am - 2:33 pmSJU-MDW

13h 34m1 stop

$243Frontier

Find Deal

Thu, Oct 23 - Wed, Oct 29

10:35 am - 8:30 pmMDW-SJU

7h 55m1 stop

7:30 am - 4:25 pmSJU-MDW

10h 55m1 stop

$267Delta

Find Deal

Tue, Jan 27 - Wed, Feb 4

10:40 am - 10:05 pmMDW-SJU

9h 25m1 stop

6:40 am - 11:25 amSJU-MDW

6h 45m1 stop

$292Southwest

Find Deal

Tue, Nov 11 - Fri, Nov 14

6:00 am - 4:18 pmMDW-PUJ

8h 18m1 stop

2:38 pm - 11:32 pmPUJ-MDW

10h 54m1 stop

$363Delta

Find Deal

Sun, Nov 16 - Thu, Nov 20

9:20 am - 2:21 pmMDW-SXM

28h 01m2 stops

3:20 pm - 1:08 pmSXM-MDW

22h 48m2 stops

$639WestJet

Find Deal

Mon, Oct 27 - Fri, Oct 31

1:47 pm - 3:40 pmMDW-AUA

23h 53m2 stops

4:30 pm - 1:07 pmAUA-MDW

22h 37m2 stops

$732WestJet

Find Deal

Sat, Nov 15 - Thu, Nov 20

Southwest flights from Chicago Midway Airport to Caribbean

Our best Southwest deals on Chicago Midway Airport to Caribbean flight tickets

Southwest

Oct 17

MDW5:50 pmChicago Midway

15h 00m

2 stops

SJU9:50 amSan Juan Luis Munoz Marin Intl

Oct 21

SJU2:45 pmSan Juan Luis Munoz Marin Intl

9h 00m

1 stop

MDW10:45 pmChicago Midway

$227

Find similar

Southwest

Nov 11

MDW10:40 amChicago Midway

9h 25m

1 stop

SJU10:05 pmSan Juan Luis Munoz Marin Intl

Nov 14

SJU6:40 amSan Juan Luis Munoz Marin Intl

6h 45m

1 stop

MDW11:25 amChicago Midway

$292

Find similar

Southwest

Oct 14

MDW5:25 amChicago Midway

7h 45m

1 stop

PUJ2:10 pmPunta Cana

Oct 21

PUJ1:40 pmPunta Cana

9h 55m

1 stop

MDW10:35 pmChicago Midway

$357

Find similar

Frontier flights from Chicago Midway Airport to Caribbean

Our best Frontier deals on Chicago Midway Airport to Caribbean flight tickets

Frontier

Oct 30

MDW1:37 pmChicago Midway

23h 42m

1 stop

SJU2:19 pmSan Juan Luis Munoz Marin Intl

Nov 3

SJU4:24 pmSan Juan Luis Munoz Marin Intl

21h 14m

1 stop

MDW11:38 amChicago Midway

$233

Find similar

Frontier

Nov 14

MDW9:15 amChicago Midway

13h 26m

1 stop

SJU12:41 amSan Juan Luis Munoz Marin Intl

Nov 16

SJU2:11 amSan Juan Luis Munoz Marin Intl

14h 22m

1 stop

MDW2:33 pmChicago Midway

$237

Find similar

Frontier

Oct 30

MDW9:15 amChicago Midway

14h 14m

1 stop

SJU12:29 amSan Juan Luis Munoz Marin Intl

Nov 2

SJU2:03 amSan Juan Luis Munoz Marin Intl

14h 30m

1 stop

MDW2:33 pmChicago Midway

$240

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 10/17

5:50 pm-9:50 am

2 stops15h 00m

San Juan Luis Munoz Marin Intl

Tue 10/21

2:45 pm-10:45 pm

1 stop9h 00m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/30

1:37 pm-2:19 pm

1 stop23h 42m

San Juan Luis Munoz Marin Intl

Mon 11/3

4:24 pm-11:38 am

1 stop21h 14m

$233

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 11/14

9:15 am-12:41 am

1 stop13h 26m

San Juan Luis Munoz Marin Intl

Sun 11/16

2:11 am-2:33 pm

1 stop14h 22m

$237

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/30

9:15 am-12:29 am

1 stop14h 14m

San Juan Luis Munoz Marin Intl

Sun 11/2

2:03 am-2:33 pm

1 stop14h 30m

$240

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/23

8:25 am-12:29 am

1 stop15h 04m

San Juan Luis Munoz Marin Intl

Wed 10/29

1:59 am-2:33 pm

1 stop13h 34m

$243

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/27

10:35 am-8:30 pm

1 stop7h 55m

San Juan Luis Munoz Marin Intl

Wed 2/4

7:30 am-4:25 pm

1 stop10h 55m

$267

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 11/11

10:40 am-10:05 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Fri 11/14

6:40 am-11:25 am

1 stop6h 45m

$292

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 11/16

6:00 am-4:18 pm

1 stop8h 18m

Punta Cana

Thu 11/20

2:38 pm-11:32 pm

1 stop10h 54m

$363

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 10/27

9:20 am-2:21 pm

2 stops28h 01m

Simpson Bay Princess Juliana

Fri 10/31

3:20 pm-1:08 pm

2 stops22h 48m

$639

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Sat 11/15

1:47 pm-3:40 pm

2 stops23h 53m

Oranjestad Reina Beatrix

Thu 11/20

4:30 pm-1:07 pm

2 stops22h 37m

$732

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 Chicago Midway Airport 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

What is the cheapest month to fly to Caribbean?

In general, November is the cheapest month to fly from Chicago Midway Airport to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $295. If you don’t want to visit Caribbean in November, then you should wait until May to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $328.

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

The cheapest day to depart from Chicago Midway Airport to Caribbean is on a Tuesday when prices can be found for as low as $59. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $510. 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 Chicago Midway Airport to Caribbean when you can find flight prices for as low as $324. 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 $510.

What is the cheapest Chicago Midway to Caribbean flight route?

Fly from Chicago Midway to Punta Cana for the best Chicago Midway - 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 Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $422 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Chicago Midway Airport for as low as $326 on momondo.

What cabin class options are available on Chicago Midway to Caribbean flights?

There is only 1 cabin class available to choose from on Chicago Midway 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 Chicago Midway Airport to Caribbean flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Caribbean.

Cheap Chicago Midway Airport to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Caribbean

Fastest flight time	3h 50m
Direct flights	Mon, Thu, Sat and Sun
Airports in Caribbean	3 airports

The fastest flight from Chicago Midway Airport to Caribbean takes 3h 50m

Direct flights go from Chicago Midway Airport to Caribbean on Monday, Thursday, Saturday and Sunday. The only airline offering direct flights is Southwest.

There are 3 airports near Caribbean: Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ), San Juan Luis Munoz Marin Intl (SJU)

Search flight deals

When did momondo last update prices for flights from Chicago Midway Airport to Caribbean?
Prices for flights from Chicago Midway Airport to Caribbean refresh daily.
How many operators does momondo search for flights from Chicago Midway Airport to Caribbean?
As of September 2025, there are 5 operators available to choose from for flights from Chicago Midway Airport to Caribbean.
How old do you have to be to fly from Chicago Midway Airport to Caribbean?
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 Chicago Midway Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents you'll need for your trip to Caribbean may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Caribbean?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Caribbean is Airbus A321-100/200, representing 17.88% of all bookings. The subsequent popular models are Boeing 737-900 at 17.32%, Boeing 737 MAX 8 at 15.08%, and Airbus A321neo at 15.08%.

Best airlines flying from Chicago Midway Airport to Caribbean

Compare and see reviews for airlines that fly from Chicago Midway Airport to Caribbean with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $133	Free Cancellation	Rating 5.8 3,174 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $149	Free Cancellation	Rating 6.3 8,019 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $299	Free Cancellation	Rating 7.4 8,924 reviews	Search United Airlines flights
Delta	PriceFrom $325	Free Cancellation	Rating 7.9 7,957 reviews	Search Delta flights
Southwest	PriceFrom $364	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights

Why use momondo?

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

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 Chicago to Caribbean for you.

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

Yes. momondo allows you to filter the results for Chicago to Caribbean flights to just show those with flexible booking policies.

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

momondo helps you find the best flight between Chicago and Caribbean by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Of course. momondo tracks the price of Chicago to Caribbean flights. All you need is a valid email address and we will do the rest; it is that quick and easy.