$98 Find Cheap Flights from Chicago Midway Airport to Caribbean Islands

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 Islands departing on 4/3. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$299
Santo Domingo
Santo Domingo1 stop$355
Montego Bay
Montego Bay1 stop$323
Oranjestad
Oranjestad1 stop$559
Nassau
Nassau1 stop$497
Kingston
Kingston1 stop$556
Simpson Bay
Simpson Bay1 stop$396
Providenciales
Providenciales1 stop$501
George Town
George Town1 stop$529
St. John's
St. John's1 stop$1,048
Aguadilla
Aguadilla1 stop$281
Punta Cana
Punta Cana2 stops$299
Santo Domingo
Santo Domingo1 stop$355
Montego Bay
Montego Bay1 stop$323
Oranjestad
Oranjestad1 stop$559
Nassau
Nassau1 stop$497
Kingston
Kingston1 stop$556
Simpson Bay
Simpson Bay1 stop$396
Providenciales
Providenciales1 stop$501
George Town
George Town1 stop$529
St. John's
St. John's1 stop$1,048
Aguadilla
Aguadilla1 stop$281

Book Cheap Midway to Caribbean Islands 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 Islands 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 Islands

Mon, Apr 27 - Thu, Apr 30
Frontier Logo
9:14 am - 9:54 am
MDW
-
SJU
23h 40m
1 stop
Frontier Logo
3:03 pm - 10:19 pm
SJU
-
MDW
8h 16m
1 stop
$205Frontier
Sun, Apr 12 - Sat, Apr 18
Frontier Logo
5:05 am - 11:18 am
MDW
-
SJU
29h 13m
1 stop
Frontier Logo
3:21 am - 8:04 am
SJU
-
MDW
29h 43m
1 stop
$211Frontier
Fri, Apr 17 - Fri, Apr 24
Frontier Logo
9:14 am - 9:54 am
MDW
-
SJU
23h 40m
1 stop
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
$214Frontier
Mon, Apr 27 - Thu, Apr 30
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
Frontier Logo
3:39 pm - 10:28 am
SJU
-
MDW
19h 49m
1 stop
$215Frontier
Tue, Apr 28 - Sat, May 2
Southwest Logo
7:00 am - 1:55 pm
MDW
-
MBJ
6h 55m
1 stop
Southwest Logo
11:35 am - 8:40 pm
MBJ
-
MDW
9h 05m
1 stop
$332Southwest
Mon, Apr 13 - Fri, Apr 17
Multiple Airlines Logo
5:30 am - 1:26 pm
MDW
-
STT
6h 56m
1 stop
Multiple Airlines Logo
5:10 pm - 10:14 pm
STT
-
MDW
30h 04m
2 stops
$356Multiple Airlines
Sun, May 31 - Sat, Jun 6
Southwest Logo
5:15 am - 2:20 pm
MDW
-
MBJ
9h 05m
1 stop
Southwest Logo
2:30 pm - 6:35 pm
MBJ
-
MDW
4h 05mnonstop
$357Southwest
Sun, Apr 26 - Sat, May 2
Multiple Airlines Logo
2:00 pm - 9:54 am
MDW
-
STT
18h 54m
1 stop
Multiple Airlines Logo
10:49 am - 10:14 pm
STT
-
MDW
12h 25m
2 stops
$374Multiple Airlines
Wed, Jun 24 - Wed, Jul 1
Delta Logo
6:00 am - 3:55 pm
MDW
-
NAS
8h 55m
1 stop
Delta Logo
3:10 pm - 9:45 pm
NAS
-
MDW
7h 35m
1 stop
$512Delta
Mon, Apr 27 - Thu, Apr 30
Delta Logo
12:52 pm - 8:00 pm
MDW
-
KIN
7h 08m
1 stop
Delta Logo
9:00 am - 10:28 pm
KIN
-
MDW
13h 28m
1 stop
$556Delta
Booking Insights

KAYAK's insights & trends for Midway to Caribbean Islands flights

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

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

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

The cheapest ticket to Caribbean Islands 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 Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $425.

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

The average price for all round-trip flights from Chicago Midway Airport to Caribbean Islands 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 Islands is generally in the morning, when round-trip flights cost $574 on average. The most expensive time of day to fly to Caribbean Islands 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 Islands?

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 $384, prices are generally cheapest when you fly direct.

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

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 Islands, 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 Islands 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 Islands?

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 Islands, 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 Islands, 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$98
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 Islands flights

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

    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 Islands.

  • 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 Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 Islands

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Caribbean Islands? 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 4324 reviews
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

10.0 ExcellentMartie, Mar 2026
LGB - BNA
Read more Southwest reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

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!

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

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!

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports