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Cheap flights from Chicago Midway Airport to Caribbean Islands 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 Islands departing on 8/23. 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 Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
1:00 pm - 10:50 pm
MDW
-
SJU
8h 50m
2 stops
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
$246Southwest
Fri, Aug 21 - Tue, Aug 25
Southwest Logo
7:50 am - 6:05 pm
MDW
-
SJU
9h 15m
2 stops
Southwest Logo
10:00 am - 6:00 pm
SJU
-
MDW
9h 00m
1 stop
$251Southwest
Sat, Aug 22 - Fri, Aug 28
Southwest Logo
7:50 am - 6:05 pm
MDW
-
SJU
9h 15m
2 stops
Southwest Logo
5:05 am - 11:00 am
SJU
-
MDW
6h 55m
1 stop
$256Southwest
Sat, Aug 22 - Sat, Aug 29
Southwest Logo
7:50 am - 6:05 pm
MDW
-
SJU
9h 15m
2 stops
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
$261Southwest
Sat, Aug 22 - Wed, Aug 26
Delta Logo
6:05 am - 4:38 pm
MDW
-
SJU
9h 33m
1 stop
Delta Logo
7:00 am - 3:44 pm
SJU
-
MDW
9h 44m
1 stop
$301Delta
Tue, Aug 18 - Mon, Aug 31
Delta Logo
6:05 am - 1:28 pm
MDW
-
SDQ
6h 23m
1 stop
Delta Logo
2:53 pm - 10:45 pm
SDQ
-
MDW
8h 52m
1 stop
$408Delta
Sun, Sep 6 - Fri, Sep 11
Delta Logo
10:56 am - 12:39 pm
MDW
-
SDQ
24h 43m
2 stops
Delta Logo
2:53 pm - 10:45 pm
SDQ
-
MDW
8h 52m
1 stop
$413Delta
Sat, Sep 5 - Sat, Sep 12
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
Frontier Logo
3:31 pm - 9:51 am
PUJ
-
MDW
19h 20m
1 stop
$468Frontier
Tue, Jul 28 - Wed, Aug 5
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
Frontier Logo
1:39 pm - 10:03 pm
MBJ
-
MDW
8h 24m
1 stop
$472Frontier
Wed, Jul 29 - Sun, Aug 16
Frontier Logo
6:05 am - 2:27 pm
MDW
-
PUJ
7h 22m
1 stop
Frontier Logo
3:37 pm - 10:47 pm
PUJ
-
MDW
8h 10m
1 stop
$480Frontier
Sat, Aug 22 - Sat, Aug 29

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Delta flights from Chicago Midway Airport to Caribbean Islands

Our best Delta deals on Chicago Midway Airport to Caribbean Islands flight tickets
Delta
Aug 18
MDW6:05 amChicago Midway
9h 33m
1 stop
SJU4:38 pmSan Juan Luis Munoz Marin Intl
Aug 31
SJU7:00 amSan Juan Luis Munoz Marin Intl
9h 44m
1 stop
MDW3:44 pmChicago Midway
$301
Delta
Aug 18
MDW10:54 amChicago Midway
10h 35m
1 stop
SJU10:29 pmSan Juan Luis Munoz Marin Intl
Aug 22
SJU7:00 amSan Juan Luis Munoz Marin Intl
9h 38m
1 stop
MDW3:38 pmChicago Midway
$356
Delta
Sep 6
MDW6:05 amChicago Midway
6h 23m
1 stop
SDQ1:28 pmSanto Domingo Las Americas
Sep 11
SDQ2:53 pmSanto Domingo Las Americas
8h 52m
1 stop
MDW10:45 pmChicago Midway
$408

Southwest flights from Chicago Midway Airport to Caribbean Islands

Our best Southwest deals on Chicago Midway Airport to Caribbean Islands flight tickets
Southwest
Aug 21
MDW1:00 pmChicago Midway
8h 50m
2 stops
SJU10:50 pmSan Juan Luis Munoz Marin Intl
Aug 25
SJU5:15 amSan Juan Luis Munoz Marin Intl
7h 50m
2 stops
MDW12:05 pmChicago Midway
$246
Southwest
Aug 22
MDW7:45 amChicago Midway
9h 20m
1 stop
SJU6:05 pmSan Juan Luis Munoz Marin Intl
Aug 28
SJU11:35 amSan Juan Luis Munoz Marin Intl
7h 25m
1 stop
MDW6:00 pmChicago Midway
$251
Southwest
Aug 22
MDW7:50 amChicago Midway
9h 15m
2 stops
SJU6:05 pmSan Juan Luis Munoz Marin Intl
Aug 29
SJU6:25 amSan Juan Luis Munoz Marin Intl
11h 40m
2 stops
MDW5:05 pmChicago Midway
$256

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 July 9, 2026.
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

Cheapest round-trip

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 8/21

1:00 pm-10:50 pm

2 stops8h 50m

San Juan Luis Munoz Marin Intl

Tue 8/25

5:15 am-12:05 pm

2 stops7h 50m

$246

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/22

7:50 am-6:05 pm

2 stops9h 15m

San Juan Luis Munoz Marin Intl

Fri 8/28

10:00 am-6:00 pm

1 stop9h 00m

$251

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/22

7:50 am-6:05 pm

2 stops9h 15m

San Juan Luis Munoz Marin Intl

Sat 8/29

5:05 am-11:00 am

1 stop6h 55m

$256

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/22

7:50 am-6:05 pm

2 stops9h 15m

San Juan Luis Munoz Marin Intl

Wed 8/26

5:15 am-12:05 pm

2 stops7h 50m

$261

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/18

6:05 am-4:38 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

Mon 8/31

7:00 am-3:44 pm

1 stop9h 44m

$301

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 9/6

6:05 am-1:28 pm

1 stop6h 23m

Santo Domingo Las Americas

Fri 9/11

2:53 pm-10:45 pm

1 stop8h 52m

$408

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 9/5

10:56 am-12:39 pm

2 stops24h 43m

Santo Domingo Las Americas

Sat 9/12

2:53 pm-10:45 pm

1 stop8h 52m

$413

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 7/28

6:05 am-2:21 pm

1 stop7h 16m

Punta Cana

Wed 8/5

3:31 pm-9:51 am

1 stop19h 20m

$468
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 7/29

6:05 am-12:27 pm

1 stop6h 22m

Montego Bay Sangster Intl

Sun 8/16

1:39 pm-10:03 pm

1 stop8h 24m

$472

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 8/22

6:05 am-2:27 pm

1 stop7h 22m

Punta Cana

Sat 8/29

3:37 pm-10:47 pm

1 stop8h 10m

$480

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 May is, on average, the cheapest month to fly to Caribbean Islands from Chicago Midway Airport, with most prices found around $172. The month of April is another great option to travel to Caribbean Islands, with average flight prices from Chicago Midway Airport averaging around $190.

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 Sunday. Travelers who choose to depart for Caribbean Islands on a Sunday will often find tickets for as low as $499. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $672. 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 Chicago Midway to Caribbean Islands flight route?

Fly from Chicago Midway to Montego Bay Sangster Intl for the best Chicago Midway - Caribbean Islands flight prices

How far in advance should I book a flight from Chicago Midway Airport 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 $393 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 $305 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway Airport 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 55m

Direct flights

Every day

Airports in Caribbean Islands

99 airports
The fastest flight from Chicago Midway Airport to Caribbean Islands takes 3h 55m
Direct flights go from Chicago Midway Airport to Caribbean Islands every day.
There are 99 airports in Caribbean Islands. 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 Islands

  • 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 $91Free CancellationRating
5.6
2,835 reviews
Search Frontier flights
DeltaPriceFrom $132Free CancellationRating
7.8
8,454 reviews
Search Delta flights
SouthwestPriceFrom $352Free CancellationRating
7.9
4,248 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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