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 63% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 3 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

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

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

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

As of February 2026, there are 3 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.

$101 Cheap Flights from Chicago Midway Airport to Caribbean in 2026

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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

Enter your travel dates to find the best prices.

6:00 am - 2:08 pm

MDW

SJU

7h 08m

1 stop

3:21 am - 10:28 am

SJU

MDW

8h 07m

1 stop

$202Frontier

Sun, Apr 26 - Thu, Apr 30

2:56 pm - 12:52 am

MDW

SJU

8h 56m

1 stop

3:19 pm - 7:59 am

SJU

MDW

17h 40m

1 stop

$203Frontier

Thu, Apr 9 - Thu, Apr 16

5:30 am - 2:01 am

MDW

SJU

19h 31m

1 stop

3:23 pm - 10:26 pm

SJU

MDW

8h 03m

1 stop

$208Frontier

Fri, Apr 10 - Fri, Apr 17

9:04 am - 2:01 am

MDW

SJU

15h 57m

1 stop

3:03 pm - 10:19 pm

SJU

MDW

8h 16m

1 stop

$213Frontier

Sun, Apr 19 - Thu, Apr 30

8:39 am - 12:28 pm

MDW

STT

26h 49m

1 stop

2:36 pm - 8:04 am

STT

MDW

18h 28m

1 stop

$290Multiple Airlines

Sun, May 3 - Wed, May 6

8:39 am - 12:28 pm

MDW

STT

26h 49m

1 stop

2:36 pm - 8:04 am

STT

MDW

18h 28m

1 stop

$304Multiple Airlines

Sun, May 3 - Wed, May 6

9:55 am - 1:45 pm

MDW

MBJ

3h 50mnonstop

11:35 am - 3:45 pm

MBJ

MDW

4h 10mnonstop

$354Southwest

Sat, May 16 - Sat, May 23

7:50 am - 11:45 am

MDW

MBJ

3h 55mnonstop

1:50 pm - 5:50 pm

MBJ

MDW

4h 00mnonstop

$373Southwest

Sun, Jun 7 - Thu, Jun 11

10:41 am - 4:33 pm

MDW

NAS

4h 52m

1 stop

1:13 pm - 10:28 pm

NAS

MDW

10h 15m

1 stop

$474Delta

Tue, Apr 14 - Thu, Apr 23

6:00 am - 11:47 am

MDW

GCM

5h 47m

1 stop

1:12 pm - 10:31 pm

GCM

MDW

9h 19m

1 stop

$499Delta

Tue, Mar 31 - Tue, Apr 7

Frontier flights from Chicago Midway Airport to Caribbean

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

Frontier

Apr 26

MDW6:00 amChicago Midway

7h 08m

1 stop

SJU2:08 pmSan Juan Luis Munoz Marin Intl

Apr 30

SJU3:21 amSan Juan Luis Munoz Marin Intl

8h 07m

1 stop

MDW10:28 amChicago Midway

$202

Frontier

Apr 9

MDW2:56 pmChicago Midway

8h 56m

1 stop

SJU12:52 amSan Juan Luis Munoz Marin Intl

Apr 16

SJU3:19 pmSan Juan Luis Munoz Marin Intl

17h 40m

1 stop

MDW7:59 amChicago Midway

$203

Frontier

Apr 10

MDW5:30 amChicago Midway

19h 31m

1 stop

SJU2:01 amSan Juan Luis Munoz Marin Intl

Apr 17

SJU3:23 pmSan Juan Luis Munoz Marin Intl

8h 03m

1 stop

MDW10:26 pmChicago Midway

$208

Delta flights from Chicago Midway Airport to Caribbean

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

Delta

Apr 21

MDW12:52 pmChicago Midway

6h 32m

1 stop

SJU8:24 pmSan Juan Luis Munoz Marin Intl

Apr 25

SJU6:15 amSan Juan Luis Munoz Marin Intl

11h 14m

1 stop

MDW4:29 pmChicago Midway

$246

Delta

Mar 3

MDW12:45 pmChicago Midway

6h 27m

1 stop

SJU9:12 pmSan Juan Luis Munoz Marin Intl

Mar 17

SJU2:44 pmSan Juan Luis Munoz Marin Intl

8h 47m

1 stop

MDW10:31 pmChicago Midway

$316

Delta

Apr 18

MDW6:00 amChicago Midway

11h 34m

2 stops

SDQ6:34 pmSanto Domingo Las Americas

Apr 25

SDQ6:05 amSanto Domingo Las Americas

12h 53m

2 stops

MDW5:58 pmChicago Midway

$451

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

Sun 4/26

6:00 am-2:08 pm

1 stop7h 08m

San Juan Luis Munoz Marin Intl

Thu 4/30

3:21 am-10:28 am

1 stop8h 07m

$202

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 4/9

2:56 pm-12:52 am

1 stop8h 56m

San Juan Luis Munoz Marin Intl

Thu 4/16

3:19 pm-7:59 am

1 stop17h 40m

$203

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 4/10

5:30 am-2:01 am

1 stop19h 31m

San Juan Luis Munoz Marin Intl

Fri 4/17

3:23 pm-10:26 pm

1 stop8h 03m

$208

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 4/19

9:04 am-2:01 am

1 stop15h 57m

San Juan Luis Munoz Marin Intl

Thu 4/30

3:03 pm-10:19 pm

1 stop8h 16m

$213

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 5/3

8:39 am-12:28 pm

1 stop26h 49m

Saint Thomas Island Cyril E King

Wed 5/6

2:36 pm-8:04 am

1 stop18h 28m

$290

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 5/3

8:39 am-12:28 pm

1 stop26h 49m

Saint Thomas Island Cyril E King

Wed 5/6

2:36 pm-8:04 am

1 stop18h 28m

$304

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/16

9:55 am-1:45 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Sat 5/23

11:35 am-3:45 pm

Nonstop4h 10m

$354

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 6/7

7:50 am-11:45 am

Nonstop3h 55m

Montego Bay Sangster Intl

Thu 6/11

1:50 pm-5:50 pm

Nonstop4h 00m

$373

ChicagoNassau

MDW - NAS

MDWNAS

Chicago Midway

Tue 4/14

10:41 am-4:33 pm

1 stop4h 52m

Nassau Intl

Thu 4/23

1:13 pm-10:28 pm

1 stop10h 15m

$474

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 3/31

6:00 am-11:47 am

1 stop5h 47m

George Town Owen Roberts Intl

Tue 4/7

1:12 pm-10:31 pm

1 stop9h 19m

$499

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, February 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 $289. If you don’t want to visit Caribbean in February, then you should wait until January to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $304.

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 $399 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 $222 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?

You could potentially save up to 47% on your flight if you consider stops on a Chicago Midway Airport to Caribbean flight.

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

Best Price Found	$579
Fastest flight time	3h 50m
Direct flights	Every day
Airports in Caribbean	195 airports

The best flight deal from Chicago Midway Airport to Caribbean found on momondo in the last 72 hours is $579

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

Direct flights go from Chicago Midway Airport to Caribbean every day.

There are 195 airports in Caribbean. From Chicago Midway Airport there are direct flights to Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ).

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 February 2026, there are 3 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 Boeing 737 MAX 8, representing 42.80% of all bookings. The subsequent popular models are Boeing 737-800 at 13.14%, Boeing 737-900 at 9.75%, and Boeing 737 MAX 9 at 8.47%.

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
Delta	PriceFrom $132	Free Cancellation	Rating 7.9 8,242 reviews	Search Delta flights
Frontier	PriceFrom $138	Free Cancellation	Rating 5.7 3,041 reviews	Search Frontier flights
Southwest	PriceFrom $379	Free Cancellation	Rating 8.0 4,301 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.