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Cheap flights from Chicago Midway Airport to Caribbean from $118

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Caribbean departing on 9/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago Midway Airport to Caribbean

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
1 stop
Southwest Logo
5:05 am - 11:00 am
SJU
-
MDW
6h 55m
1 stop
$256Southwest
Wed, Aug 19 - Sat, Aug 22
Southwest Logo
7:05 am - 6:15 pm
MDW
-
SJU
10h 10m
1 stop
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
$266Southwest
Sat, Aug 15 - Wed, Aug 19
Southwest Logo
7:50 pm - 9:25 am
MDW
-
SJU
12h 35m
1 stop
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
1 stop
$276Southwest
Fri, Sep 4 - Tue, Sep 8
Southwest Logo
7:30 am - 7:00 pm
MDW
-
SJU
10h 30m
1 stop
Southwest Logo
8:20 am - 4:55 pm
SJU
-
MDW
9h 35m
2 stops
$286Southwest
Tue, Aug 11 - Tue, Aug 18
Delta Logo
6:05 am - 4:38 pm
MDW
-
SJU
9h 33m
1 stop
Delta Logo
7:00 am - 4:15 pm
SJU
-
MDW
10h 15m
1 stop
$304Delta
Tue, Aug 11 - Tue, Aug 18
Delta Logo
6:05 am - 1:42 pm
MDW
-
SJU
6h 37m
1 stop
Delta Logo
7:00 am - 3:38 pm
SJU
-
MDW
9h 38m
1 stop
$306Delta
Mon, Aug 24 - Sat, Aug 29
Delta Logo
6:05 am - 1:42 pm
MDW
-
SJU
6h 37m
1 stop
Delta Logo
7:00 am - 4:15 pm
SJU
-
MDW
10h 15m
1 stop
$314Delta
Sat, Aug 15 - Tue, Aug 18
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
Frontier Logo
11:46 am - 10:03 pm
PUJ
-
MDW
11h 17m
2 stops
$447Frontier
Tue, Jul 21 - Tue, Aug 4
Frontier Logo
6:00 am - 2:29 pm
MDW
-
PUJ
7h 29m
1 stop
Frontier Logo
3:39 pm - 10:58 am
PUJ
-
MDW
20h 19m
1 stop
$458Frontier
Tue, Sep 1 - Tue, Sep 8
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
Frontier Logo
11:46 am - 10:03 pm
PUJ
-
MDW
11h 17m
2 stops
$461Frontier
Tue, Jul 21 - Wed, Jul 22

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Southwest flights from Chicago Midway Airport to Caribbean

Our best Southwest deals on Chicago Midway Airport to Caribbean flight tickets
Southwest
Aug 19
MDW12:45 pmChicago Midway
8h 15m
1 stop
SJU10:00 pmSan Juan Luis Munoz Marin Intl
Aug 22
SJU5:05 amSan Juan Luis Munoz Marin Intl
6h 55m
1 stop
MDW11:00 amChicago Midway
$256
Southwest
Aug 15
MDW7:05 amChicago Midway
10h 10m
1 stop
SJU6:15 pmSan Juan Luis Munoz Marin Intl
Aug 19
SJU5:15 amSan Juan Luis Munoz Marin Intl
7h 50m
2 stops
MDW12:05 pmChicago Midway
$266
Southwest
Sep 4
MDW7:50 pmChicago Midway
12h 35m
1 stop
SJU9:25 amSan Juan Luis Munoz Marin Intl
Sep 8
SJU5:15 amSan Juan Luis Munoz Marin Intl
7h 50m
1 stop
MDW12:05 pmChicago Midway
$276

Delta flights from Chicago Midway Airport to Caribbean

Our best Delta deals on Chicago Midway Airport to Caribbean flight tickets
Delta
Aug 11
MDW6:05 amChicago Midway
9h 33m
1 stop
SJU4:38 pmSan Juan Luis Munoz Marin Intl
Aug 18
SJU7:00 amSan Juan Luis Munoz Marin Intl
10h 15m
1 stop
MDW4:15 pmChicago Midway
$304
Delta
Aug 24
MDW6:05 amChicago Midway
6h 37m
1 stop
SJU1:42 pmSan Juan Luis Munoz Marin Intl
Aug 29
SJU7:00 amSan Juan Luis Munoz Marin Intl
9h 38m
1 stop
MDW3:38 pmChicago Midway
$306
Delta
Aug 15
MDW6:05 amChicago Midway
6h 37m
1 stop
SJU1:42 pmSan Juan Luis Munoz Marin Intl
Aug 18
SJU7:00 amSan Juan Luis Munoz Marin Intl
10h 15m
1 stop
MDW4:15 pmChicago Midway
$314

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated June 15, 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 8/19

12:45 pm-10:00 pm

1 stop8h 15m

San Juan Luis Munoz Marin Intl

Sat 8/22

5:05 am-11:00 am

1 stop6h 55m

$256

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/15

7:05 am-6:15 pm

1 stop10h 10m

San Juan Luis Munoz Marin Intl

Wed 8/19

5:15 am-12:05 pm

2 stops7h 50m

$266

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 9/4

7:50 pm-9:25 am

1 stop12h 35m

San Juan Luis Munoz Marin Intl

Tue 9/8

5:15 am-12:05 pm

1 stop7h 50m

$276

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/11

7:30 am-7:00 pm

1 stop10h 30m

San Juan Luis Munoz Marin Intl

Tue 8/18

8:20 am-4:55 pm

2 stops9h 35m

$286

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/11

6:05 am-4:38 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

Tue 8/18

7:00 am-4:15 pm

1 stop10h 15m

$304

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 8/24

6:05 am-1:42 pm

1 stop6h 37m

San Juan Luis Munoz Marin Intl

Sat 8/29

7:00 am-3:38 pm

1 stop9h 38m

$306

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/15

6:05 am-1:42 pm

1 stop6h 37m

San Juan Luis Munoz Marin Intl

Tue 8/18

7:00 am-4:15 pm

1 stop10h 15m

$314

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 7/21

6:05 am-2:21 pm

1 stop7h 16m

Punta Cana

Tue 8/4

11:46 am-10:03 pm

2 stops11h 17m

$447

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 9/1

6:00 am-2:29 pm

1 stop7h 29m

Punta Cana

Tue 9/8

3:39 pm-10:58 am

1 stop20h 19m

$458

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 7/21

6:05 am-2:21 pm

1 stop7h 16m

Punta Cana

Wed 7/22

11:46 am-10:03 pm

2 stops11h 17m

$461

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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

What is the cheapest month to fly to Caribbean?

In general, April 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 $91. If you don’t want to visit Caribbean in April, then you should wait until January to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $133.

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 Sunday when prices can be found for as low as $499. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $658. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

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 from Chicago Midway Airport 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 $380 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 $274 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway Airport 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 19% 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

$635

Fastest flight time

4h 25m

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 $635
The fastest flight from Chicago Midway Airport to Caribbean takes 4h 25m
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), San Juan Luis Munoz Marin Intl (SJU).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Caribbean

  • 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?

  • 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?

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
DeltaPriceFrom $132Free CancellationRating
7.9
8,395 reviews
Search Delta flights
FrontierPriceFrom $138Free CancellationRating
5.6
2,888 reviews
Search Frontier flights
SouthwestPriceFrom $352Free CancellationRating
7.9
4,235 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.

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Find better results for your trip to Caribbean

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