$128 Find Cheap Flights from Chicago Midway Airport to Caribbean - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Caribbean departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Midway to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$465
Santo Domingo
Santo Domingo1 stop$408
Montego Bay
Montego Bay1 stop$459
Oranjestad
Oranjestad1 stop$651
Santiago de los Caballeros
Santiago de los Caballeros2 stops$562
Nassau
Nassau1 stop$322
Saint Thomas Island
Saint Thomas Island1 stop$428
Kingston
Kingston1 stop$464
Simpson Bay
Simpson Bay1 stop$383
Providenciales
Providenciales1 stop$611
George Town
George Town1 stop$426
St. John's
St. John's1 stop$680
Punta Cana
Punta Cana1 stop$465
Santo Domingo
Santo Domingo1 stop$408
Montego Bay
Montego Bay1 stop$459
Oranjestad
Oranjestad1 stop$651
Santiago de los Caballeros
Santiago de los Caballeros2 stops$562
Nassau
Nassau1 stop$322
Saint Thomas Island
Saint Thomas Island1 stop$428
Kingston
Kingston1 stop$464
Simpson Bay
Simpson Bay1 stop$383
Providenciales
Providenciales1 stop$611
George Town
George Town1 stop$426
St. John's
St. John's1 stop$680

Book Cheap Midway to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Caribbean

Fri, Aug 21 - Tue, Aug 25
Southwest Logo
11:15 am - 10:10 pm
MDW
-
SJU
9h 55m
1 stop
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
$246Southwest
Sat, Aug 22 - Fri, Aug 28
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 - Sat, Aug 29
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 29 - Sat, Sep 5
Southwest Logo
7:50 am - 6:05 pm
MDW
-
SJU
9h 15m
2 stops
Southwest Logo
6:25 am - 4:45 pm
SJU
-
MDW
11h 20m
2 stops
$261Southwest
Tue, Aug 18 - Mon, Aug 31
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
Sun, Sep 6 - Fri, Sep 11
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
Sat, Sep 5 - 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
Tue, Jul 28 - Wed, Aug 5
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
Wed, Jul 29 - Sun, Aug 16
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
Tue, Aug 4 - Tue, Aug 11
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
Frontier Logo
9:29 pm - 9:51 am
PUJ
-
MDW
37h 22m
2 stops
$480Frontier
Booking Insights

KAYAK's insights & trends for Midway to Caribbean flights

Get data-powered insights and trends into flights from Midway to Caribbean to help you find the cheapest flights, the best time to fly and much more.

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Chicago Midway Airport found in the last 5 days was to Montego Bay, at $467 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $578.

What is the cheapest time of day to fly to Caribbean?

The average price for all round-trip flights from Chicago Midway Airport to Caribbean depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean is generally in the morning, when round-trip flights cost $666 on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $666.

Can I save money by flying with a layover from Chicago Midway Airport to Caribbean?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $598, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Caribbean is April, when tickets cost $91 (return) on average. On the other hand, the most expensive months are November and September, when the average cost of round-trip tickets is $279 and $278 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Caribbean, you should book around 3 weeks before departure, which saves you about 33% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$128
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 28% increase in price.
Flight from Chicago Midway Airport to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago Midway Airport to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago Midway Airport to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Chicago Midway Airport (MDW)