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Cheap flights from Chicago Midway Airport to Caribbean Islands 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 Islands departing on 10/17. 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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Find the cheapest flights from Chicago Midway Airport to Caribbean Islands

Cheap round-trip flights

Southwest Logo
5:50 pm - 9:50 amMDW-SJU
15h 00m2 stops
Southwest Logo
2:45 pm - 10:45 pmSJU-MDW
9h 00m1 stop
$227Southwest
Find Deal
Fri, Oct 17 - Tue, Oct 21
Frontier Logo
1:37 pm - 2:19 pmMDW-SJU
23h 42m1 stop
Frontier Logo
4:24 pm - 11:38 amSJU-MDW
21h 14m1 stop
$233Frontier
Find Deal
Thu, Oct 30 - Mon, Nov 3
Frontier Logo
9:15 am - 12:41 amMDW-SJU
13h 26m1 stop
Frontier Logo
2:11 am - 2:33 pmSJU-MDW
14h 22m1 stop
$237Frontier
Find Deal
Fri, Nov 14 - Sun, Nov 16
Frontier Logo
9:15 am - 12:29 amMDW-SJU
14h 14m1 stop
Frontier Logo
2:03 am - 2:33 pmSJU-MDW
14h 30m1 stop
$240Frontier
Find Deal
Thu, Oct 30 - Sun, Nov 2
Frontier Logo
8:25 am - 12:29 amMDW-SJU
15h 04m1 stop
Frontier Logo
1:59 am - 2:33 pmSJU-MDW
13h 34m1 stop
$243Frontier
Find Deal
Thu, Oct 23 - Wed, Oct 29
Delta Logo
10:35 am - 8:30 pmMDW-SJU
7h 55m1 stop
Delta Logo
7:30 am - 4:25 pmSJU-MDW
10h 55m1 stop
$267Delta
Find Deal
Tue, Jan 27 - Wed, Feb 4
Southwest Logo
10:40 am - 10:05 pmMDW-SJU
9h 25m1 stop
Southwest Logo
6:40 am - 11:25 amSJU-MDW
6h 45m1 stop
$292Southwest
Find Deal
Tue, Nov 11 - Fri, Nov 14
Delta Logo
6:00 am - 4:18 pmMDW-PUJ
8h 18m1 stop
Delta Logo
2:38 pm - 11:32 pmPUJ-MDW
10h 54m1 stop
$363Delta
Find Deal
Sun, Nov 16 - Thu, Nov 20
WestJet Logo
9:20 am - 2:21 pmMDW-SXM
28h 01m2 stops
WestJet Logo
3:20 pm - 1:08 pmSXM-MDW
22h 48m2 stops
$639WestJet
Find Deal
Mon, Oct 27 - Fri, Oct 31
WestJet Logo
1:47 pm - 3:40 pmMDW-AUA
23h 53m2 stops
WestJet Logo
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 Islands

Our best Southwest deals on Chicago Midway Airport to Caribbean Islands 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 Islands

Our best Frontier deals on Chicago Midway Airport to Caribbean Islands 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

 
Customize your flight search to find flights from Chicago Midway Airport to Caribbean Islands 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 September 16, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Caribbean Islands 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
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See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Chicago Midway Airport to Caribbean Islands

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 Islands?

The month of November is, on average, the cheapest month to fly to Caribbean Islands from Chicago Midway Airport, with most prices found around $295. The month of May is another great option to travel to Caribbean Islands, with average flight prices from Chicago Midway Airport averaging around $328.

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

The cheapest day to depart from Chicago Midway Airport to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets 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 Islands.

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

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Chicago Midway Airport to Caribbean Islands in the evening for as low as $324. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $510. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago Midway to Caribbean Islands flight route?

Fly from Chicago Midway to Punta Cana for the best Chicago Midway - Caribbean Islands flight prices

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands 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 Islands from Chicago Midway Airport for as low as $326 on momondo.

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

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

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

Cheap Chicago Midway Airport to Caribbean Islands flight deals and tips

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

Fastest flight time

3h 50m

Direct flights

Mon, Thu, Sat and Sun

Airports in Caribbean Islands

3 airports
The fastest flight from Chicago Midway Airport to Caribbean Islands takes 3h 50m
Direct flights go from Chicago Midway Airport to Caribbean Islands on Monday, Thursday, Saturday and Sunday. There are no airlines offering direct flights.
There are 3 airports near Caribbean Islands: 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 Islands?

    Prices for flights from Chicago Midway Airport to Caribbean Islands were last updated today.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Caribbean Islands.

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

    The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking 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 Islands?

Best airlines flying from Chicago Midway Airport to Caribbean Islands

Compare and see reviews for airlines that fly from Chicago Midway Airport to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $133Free CancellationRating
5.8
3,174 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,019 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $299Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights
DeltaPriceFrom $325Free CancellationRating
7.9
7,957 reviews
Search Delta flights
SouthwestPriceFrom $364Free CancellationRating
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 Islands?

Finding the right flight to Caribbean Islands from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Caribbean Islands quick and easy, saving you time and money.

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

Yes. All flights to Caribbean Islands from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Caribbean Islands from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Caribbean Islands trip

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