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Cheap flights from Chicago Midway Airport to Caribbean from $114

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 5/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to Caribbean

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
10:35 am - 10:23 pm
MDW
-
SJU
10h 48m
1 stop
Delta Logo
2:40 pm - 9:46 pm
SJU
-
MDW
8h 06m
1 stop
$226Delta
Tue, Aug 11 - Tue, Aug 18
Delta Logo
10:55 am - 8:45 pm
MDW
-
SJU
8h 50m
1 stop
Delta Logo
1:06 pm - 9:46 pm
SJU
-
MDW
9h 40m
1 stop
$236Delta
Sat, Aug 8 - Thu, Aug 13
Southwest Logo
2:55 pm - 10:15 pm
MDW
-
SJU
6h 20m
1 stop
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
$246Southwest
Thu, Aug 27 - Tue, Sep 1
Frontier Logo
4:52 pm - 2:08 am
MDW
-
SJU
8h 16m
1 stop
Frontier Logo
3:03 am - 3:57 pm
SJU
-
MDW
13h 54m
1 stop
$251Frontier
Mon, May 11 - Thu, May 14
Frontier Logo
4:52 pm - 2:08 am
MDW
-
SJU
8h 16m
1 stop
Frontier Logo
3:03 am - 3:57 pm
SJU
-
MDW
13h 54m
1 stop
$256Frontier
Mon, May 11 - Thu, May 14
Delta Logo
10:55 am - 10:29 pm
MDW
-
SJU
10h 34m
1 stop
Delta Logo
1:06 pm - 9:46 pm
SJU
-
MDW
9h 40m
1 stop
$266Delta
Sat, Aug 8 - Thu, Aug 13
Southwest Logo
2:55 pm - 10:15 pm
MDW
-
SJU
6h 20m
1 stop
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
1 stop
$276Southwest
Thu, Aug 20 - Tue, Aug 25
Frontier Logo
4:52 pm - 2:08 am
MDW
-
SJU
8h 16m
1 stop
Frontier Logo
11:00 am - 11:09 am
SJU
-
MDW
25h 09m
2 stops
$277Frontier
Mon, May 11 - Mon, May 18
Multiple Airlines Logo
4:52 pm - 2:16 pm
MDW
-
STT
20h 24m
1 stop
Multiple Airlines Logo
3:21 pm - 11:09 am
STT
-
MDW
44h 48m
2 stops
$373Multiple Airlines
Fri, May 8 - Sun, May 17
Multiple Airlines Logo
4:52 pm - 2:16 pm
MDW
-
STT
20h 24m
1 stop
Multiple Airlines Logo
3:21 pm - 11:09 am
STT
-
MDW
44h 48m
2 stops
$374Multiple Airlines
Fri, May 8 - Sun, May 17

Frontier flights from Chicago Midway Airport to Caribbean

Our best Frontier deals on Chicago Midway Airport to Caribbean flight tickets
Frontier
May 12
MDW6:00 amChicago Midway
7h 07m
1 stop
SJU2:07 pmSan Juan Luis Munoz Marin Intl
May 15
SJU6:00 amSan Juan Luis Munoz Marin Intl
10h 57m
1 stop
MDW3:57 pmChicago Midway
$227
Frontier
May 5
MDW6:00 amChicago Midway
7h 07m
1 stop
SJU2:07 pmSan Juan Luis Munoz Marin Intl
May 14
SJU3:33 pmSan Juan Luis Munoz Marin Intl
25h 24m
1 stop
MDW3:57 pmChicago Midway
$242
Frontier
May 11
MDW4:52 pmChicago Midway
8h 16m
1 stop
SJU2:08 amSan Juan Luis Munoz Marin Intl
May 14
SJU3:03 amSan Juan Luis Munoz Marin Intl
13h 54m
1 stop
MDW3:57 pmChicago Midway
$251

Southwest flights from Chicago Midway Airport to Caribbean

Our best Southwest deals on Chicago Midway Airport to Caribbean flight tickets
Southwest
Apr 28
MDW7:45 amChicago Midway
9h 25m
1 stop
SJU6:10 pmSan Juan Luis Munoz Marin Intl
Apr 30
SJU1:00 pmSan Juan Luis Munoz Marin Intl
8h 50m
1 stop
MDW8:50 pmChicago Midway
$266
Southwest
Apr 29
MDW1:00 pmChicago Midway
8h 40m
1 stop
SJU10:40 pmSan Juan Luis Munoz Marin Intl
May 6
SJU5:35 amSan Juan Luis Munoz Marin Intl
9h 10m
1 stop
MDW1:45 pmChicago Midway
$296
Southwest
Jul 26
MDW7:50 amChicago Midway
3h 55m
MBJ11:45 amMontego Bay Sangster Intl
Jul 30
MBJ1:50 pmMontego Bay Sangster Intl
4h 00m
MDW5:50 pmChicago Midway
$318

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 April 26, 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

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/11

10:35 am-10:23 pm

1 stop10h 48m

San Juan Luis Munoz Marin Intl

Tue 8/18

2:40 pm-9:46 pm

1 stop8h 06m

$226

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/8

10:55 am-8:45 pm

1 stop8h 50m

San Juan Luis Munoz Marin Intl

Thu 8/13

1:06 pm-9:46 pm

1 stop9h 40m

$236
Quickest round-trip

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 8/27

2:55 pm-10:15 pm

1 stop6h 20m

San Juan Luis Munoz Marin Intl

Tue 9/1

5:15 am-12:05 pm

2 stops7h 50m

$246

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 5/11

4:52 pm-2:08 am

1 stop8h 16m

San Juan Luis Munoz Marin Intl

Thu 5/14

3:03 am-3:57 pm

1 stop13h 54m

$251

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 5/11

4:52 pm-2:08 am

1 stop8h 16m

San Juan Luis Munoz Marin Intl

Thu 5/14

3:03 am-3:57 pm

1 stop13h 54m

$256

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/8

10:55 am-10:29 pm

1 stop10h 34m

San Juan Luis Munoz Marin Intl

Thu 8/13

1:06 pm-9:46 pm

1 stop9h 40m

$266

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 8/20

2:55 pm-10:15 pm

1 stop6h 20m

San Juan Luis Munoz Marin Intl

Tue 8/25

5:15 am-12:05 pm

1 stop7h 50m

$276

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 5/11

4:52 pm-2:08 am

1 stop8h 16m

San Juan Luis Munoz Marin Intl

Mon 5/18

11:00 am-11:09 am

2 stops25h 09m

$277

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 5/8

4:52 pm-2:16 pm

1 stop20h 24m

Saint Thomas Island Cyril E King

Sun 5/17

3:21 pm-11:09 am

2 stops44h 48m

$373

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 5/8

4:52 pm-2:16 pm

1 stop20h 24m

Saint Thomas Island Cyril E King

Sun 5/17

3:21 pm-11:09 am

2 stops44h 48m

$374

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, 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 $271. 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 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 $581. 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 $382 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 $262 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 36% 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

$517

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 $517
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), 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
8,459 reviews
Search Delta flights
FrontierPriceFrom $138Free CancellationRating
5.6
2,976 reviews
Search Frontier flights
SouthwestPriceFrom $352Free CancellationRating
8.0
4,327 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

Popular cities in Caribbean

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