$104 Find Cheap Flights from Chicago Midway Airport to Caribbean

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 4/13. 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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Flight Deals

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$359
Santo Domingo
Santo Domingo1 stop$359
Montego Bay
Montego Baynonstop$318
Oranjestad
Oranjestad1 stop$521
Nassau
Nassau1 stop$484
Kingston
Kingston1 stop$606
Simpson Bay
Simpson Bay1 stop$521
Providenciales
Providenciales1 stop$502
George Town
George Town1 stop$524
St. John's
St. John's2 stops$685
Aguadilla
Aguadilla1 stop$243
Punta Cana
Punta Cana1 stop$359
Santo Domingo
Santo Domingo1 stop$359
Montego Bay
Montego Baynonstop$318
Oranjestad
Oranjestad1 stop$521
Nassau
Nassau1 stop$484
Kingston
Kingston1 stop$606
Simpson Bay
Simpson Bay1 stop$521
Providenciales
Providenciales1 stop$502
George Town
George Town1 stop$524
St. John's
St. John's2 stops$685
Aguadilla
Aguadilla1 stop$243

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

Thu, Apr 9 - Thu, Apr 16
Frontier Logo
2:56 pm - 12:52 am
MDW
-
SJU
8h 56m
1 stop
Frontier Logo
3:03 pm - 10:19 pm
SJU
-
MDW
8h 16m
1 stop
$220Frontier
Thu, Apr 9 - Thu, Apr 16
Frontier Logo
2:56 pm - 12:52 am
MDW
-
SJU
8h 56m
1 stop
Frontier Logo
6:30 am - 7:59 am
SJU
-
MDW
26h 29m
1 stop
$222Frontier
Fri, Apr 10 - Fri, Apr 17
Frontier Logo
6:30 am - 1:01 am
MDW
-
SJU
17h 31m
1 stop
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
$224Frontier
Fri, Apr 10 - Wed, Apr 15
Frontier Logo
5:30 am - 11:40 pm
MDW
-
SJU
17h 10m
1 stop
Frontier Logo
10:54 am - 8:04 am
SJU
-
MDW
22h 10m
1 stop
$229Frontier
Wed, Apr 8 - Tue, Apr 14
Frontier Logo
2:56 pm - 12:52 am
MDW
-
SJU
8h 56m
1 stop
Frontier Logo
3:08 am - 8:04 am
SJU
-
MDW
29h 56m
1 stop
$230Frontier
Fri, Jun 12 - Wed, Jun 17
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
$318Southwest
Fri, Jun 12 - Wed, Jun 17
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
Southwest Logo
2:20 pm - 10:00 pm
MBJ
-
MDW
7h 40m
1 stop
$328Southwest
Mon, Apr 20 - Wed, Apr 22
Multiple Airlines Logo
9:14 am - 9:54 am
MDW
-
STT
23h 40m
1 stop
Multiple Airlines Logo
10:49 am - 7:26 am
STT
-
MDW
21h 37m
1 stop
$335Multiple Airlines
Sun, Apr 12 - Tue, Apr 21
Multiple Airlines Logo
5:05 am - 1:26 pm
MDW
-
STT
7h 21m
1 stop
Multiple Airlines Logo
12:25 pm - 10:14 pm
STT
-
MDW
10h 49m
2 stops
$352Multiple Airlines
Sat, Jul 25 - Tue, Jul 28
Delta Logo
6:00 am - 2:10 pm
MDW
-
AUA
7h 10m
1 stop
Delta Logo
3:25 pm - 9:45 pm
AUA
-
MDW
7h 20m
1 stop
$609Delta
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 72 hours was to Montego Bay, at $297 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Montego Bay (MBJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $297.

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 $574 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 $574.

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 $618, 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 February, when tickets cost $271 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $475 and $470 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$104
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 15% lower on average.
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.

Reviews of the top 3 airlines serving from Midway to Caribbean

 
Need help choosing which airline to fly with from Midway to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4318 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

First of all we hade waited 3 hours in the airplane waiting to leave. Second the return schedule was changed and it messed up my entire vaction. I won't buy never again another flight and recommend to nobody traveling with them.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports