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

Frontier, Southwest, and Delta 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 70% 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.

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

As of December 2025, 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.

$115 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

Enter your travel dates to find the best prices.

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

6:00 am - 3:06 pm

MDW

SJU

7h 06m1 stop

6:30 am - 6:13 pm

SJU

MDW

12h 43m1 stop

$196Frontier

Tue, Mar 3 - Tue, Mar 10

8:00 am - 1:27 pm

MDW

SJU

27h 27m1 stop

5:25 pm - 2:26 pm

SJU

MDW

23h 01m1 stop

$197Frontier

Sat, Feb 14 - Wed, Feb 18

5:01 pm - 3:01 pm

MDW

PUJ

20h 00m1 stop

1:10 pm - 2:55 pm

PUJ

MDW

27h 45m1 stop

$309Multiple Airlines

Fri, Feb 6 - Fri, Feb 13

5:01 pm - 3:01 pm

MDW

PUJ

20h 00m1 stop

1:10 pm - 2:55 pm

PUJ

MDW

27h 45m1 stop

$314Multiple Airlines

Fri, Feb 6 - Fri, Feb 13

6:00 am - 2:17 pm

MDW

SDQ

6h 17m1 stop

3:42 pm - 10:42 pm

SDQ

MDW

9h 00m1 stop

$390Delta

Wed, Feb 18 - Fri, Feb 27

6:30 am - 3:35 pm

MDW

MBJ

9h 05m1 stop

4:55 pm - 9:51 am

MBJ

MDW

16h 56m1 stop

$391Delta

Sun, Apr 12 - Fri, Apr 17

7:50 pm - 12:55 pm

MDW

GCM

16h 05m2 stops

1:50 pm - 10:05 pm

GCM

MDW

9h 15m2 stops

$411Southwest

Thu, Jan 8 - Mon, Jan 12

7:00 am - 1:55 pm

MDW

MBJ

6h 55m1 stop

11:35 am - 3:45 pm

MBJ

MDW

4h 10mnonstop

$425Southwest

Tue, May 5 - Sat, May 9

6:14 pm - 12:55 pm

MDW

AUA

16h 41m1 stop

2:10 pm - 10:22 pm

AUA

MDW

10h 12m1 stop

$469KLM

Mon, Jan 19 - Wed, Jan 28

Frontier flights from Chicago Midway Airport to Caribbean

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

Our best Southwest deals on Chicago Midway Airport 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

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

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

MDW - SJU

MDWSJU

Chicago Midway

Tue 3/3

6:00 am-3:06 pm

1 stop7h 06m

San Juan Luis Munoz Marin Intl

Tue 3/10

6:30 am-6:13 pm

1 stop12h 43m

$196

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 2/14

8:00 am-1:27 pm

1 stop27h 27m

San Juan Luis Munoz Marin Intl

Wed 2/18

5:25 pm-2:26 pm

1 stop23h 01m

$197

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 2/6

5:01 pm-3:01 pm

1 stop20h 00m

Punta Cana

Fri 2/13

1:10 pm-2:55 pm

1 stop27h 45m

$309

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 2/6

5:01 pm-3:01 pm

1 stop20h 00m

Punta Cana

Fri 2/13

1:10 pm-2:55 pm

1 stop27h 45m

$314

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 2/18

6:00 am-2:17 pm

1 stop6h 17m

Santo Domingo Las Americas

Fri 2/27

3:42 pm-10:42 pm

1 stop9h 00m

$390

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 4/12

6:30 am-3:35 pm

1 stop9h 05m

Montego Bay Sangster Intl

Fri 4/17

4:55 pm-9:51 am

1 stop16h 56m

$391

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 1/8

7:50 pm-12:55 pm

2 stops16h 05m

George Town Owen Roberts Intl

Mon 1/12

1:50 pm-10:05 pm

2 stops9h 15m

$411

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 5/5

7:00 am-1:55 pm

1 stop6h 55m

Montego Bay Sangster Intl

Sat 5/9

11:35 am-3:45 pm

Nonstop4h 10m

$425

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Mon 1/19

6:14 pm-12:55 pm

1 stop16h 41m

Oranjestad Reina Beatrix

Wed 1/28

2:10 pm-10:22 pm

1 stop10h 12m

$469

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

Other information

What is the cheapest month to fly to Caribbean?

In general, May 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 $328. If you don’t want to visit Caribbean in May, then you should wait until February to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $344.

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 $526. 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 $530.

What is the cheapest Chicago Midway to Caribbean flight route?

Fly from Chicago Midway to Montego Bay Sangster Intl 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 $424 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 $336 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 64% 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	$381
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 $381

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 December 2025, 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 36.42% of all bookings. The subsequent popular models are Boeing 737-800 at 15.89%, Boeing 737-900 at 9.27%, and Airbus A321-100/200 at 8.61%.

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 $144	Free Cancellation	Rating 5.8 3,081 reviews	Search Frontier flights
Delta	PriceFrom $325	Free Cancellation	Rating 7.9 8,005 reviews	Search Delta flights
Southwest	PriceFrom $381	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 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.