$108 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 5/10. 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$306
Santo Domingo
Santo Domingo1 stop$403
Montego Bay
Montego Bay1 stop$308
Oranjestad
Oranjestad1 stop$465
Nassau
Nassau1 stop$512
Kingston
Kingston1 stop$567
Simpson Bay
Simpson Bay1 stop$515
Providenciales
Providenciales1 stop$524
George Town
George Town1 stop$520
Aguadilla
Aguadilla1 stop$305
St. John's
St. John's1 stop$912
Punta Cana
Punta Cana1 stop$306
Santo Domingo
Santo Domingo1 stop$403
Montego Bay
Montego Bay1 stop$308
Oranjestad
Oranjestad1 stop$465
Nassau
Nassau1 stop$512
Kingston
Kingston1 stop$567
Simpson Bay
Simpson Bay1 stop$515
Providenciales
Providenciales1 stop$524
George Town
George Town1 stop$520
Aguadilla
Aguadilla1 stop$305
St. John's
St. John's1 stop$912

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

Sat, Apr 25 - Sat, May 2
Frontier Logo
6:00 am - 2:33 pm
MDW
-
SJU
7h 33m
1 stop
Frontier Logo
9:58 am - 7:41 am
SJU
-
MDW
22h 43m
1 stop
$226Frontier
Sat, Apr 25 - Thu, Apr 30
Frontier Logo
9:14 am - 10:48 pm
MDW
-
SJU
12h 34m
1 stop
Frontier Logo
3:21 am - 10:28 am
SJU
-
MDW
8h 07m
1 stop
$227Frontier
Mon, May 11 - Sat, May 30
Frontier Logo
4:52 pm - 1:15 pm
MDW
-
SJU
19h 23m
1 stop
Frontier Logo
6:25 am - 2:12 pm
SJU
-
MDW
8h 47m
1 stop
$230Frontier
Sat, May 2 - Thu, May 7
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
Frontier Logo
6:09 pm - 3:57 pm
SJU
-
MDW
22h 48m
1 stop
$231Frontier
Wed, Aug 5 - Wed, Aug 12
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
2 stops
Southwest Logo
11:50 am - 5:40 pm
SJU
-
MDW
6h 50m
1 stop
$246Southwest
Mon, Apr 27 - Wed, Apr 29
Multiple Airlines Logo
6:00 am - 7:14 pm
MDW
-
SJU
12h 14m
1 stop
Multiple Airlines Logo
3:21 am - 7:31 pm
SJU
-
MDW
17h 10m
2 stops
$258Multiple Airlines
Sun, Jul 26 - Thu, Jul 30
Southwest Logo
7:50 am - 11:45 am
MDW
-
MBJ
3h 55mnonstop
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
$318Southwest
Sat, Apr 25 - Fri, May 1
Multiple Airlines Logo
9:14 am - 9:54 am
MDW
-
STT
23h 40m
1 stop
Multiple Airlines Logo
10:49 am - 4:13 pm
STT
-
MDW
30h 24m
1 stop
$363Multiple Airlines
Sun, Sep 6 - Tue, Sep 15
Delta Logo
6:00 am - 1:12 pm
MDW
-
SDQ
6h 12m
1 stop
Delta Logo
2:56 pm - 9:46 pm
SDQ
-
MDW
7h 50m
1 stop
$502Delta
Wed, May 6 - Tue, Jun 23
Delta Logo
6:00 am - 1:12 pm
MDW
-
SDQ
6h 12m
1 stop
Delta Logo
7:35 pm - 10:07 am
SDQ
-
MDW
15h 32m
2 stops
$507Delta
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 $307 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 $526.

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 $581 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 $581.

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 $625, 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 $483 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$108
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Chicago Midway Airport to Montego Bay

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 4331 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
Airline reviews

The new boarding process was easy and straightforward. Very pleasant.

10.0 ExcellentAnonymous, Apr 2026
LAS - OKC
Read more Southwest reviews

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

Okay considering we had weather delays which the Pilot notified us of immediately!

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

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.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports