$110 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 11/11. 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

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 Cananonstop$331
Santo Domingo
Santo Domingo2 stops$375
Montego Bay
Montego Bay1 stop$371
Oranjestad
Oranjestad1 stop$426
Nassau
Nassau1 stop$345
Simpson Bay
Simpson Bay1 stop$365
Kingston
Kingston1 stop$506
Providenciales
Providenciales1 stop$352
George Town
George Town1 stop$377
St. John's
St. John's2 stops$842
Aguadilla
Aguadilla1 stop$278
Punta Cana
Punta Cananonstop$331
Santo Domingo
Santo Domingo2 stops$375
Montego Bay
Montego Bay1 stop$371
Oranjestad
Oranjestad1 stop$426
Nassau
Nassau1 stop$345
Simpson Bay
Simpson Bay1 stop$365
Kingston
Kingston1 stop$506
Providenciales
Providenciales1 stop$352
George Town
George Town1 stop$377
St. John's
St. John's2 stops$842
Aguadilla
Aguadilla1 stop$278

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

Wed, Nov 26 - Thu, Dec 11
Frontier Logo
3:47 pm - 1:12 amMDW-SJU
7h 25m1 stop
Frontier Logo
7:00 am - 2:05 pmSJU-MDW
9h 05m1 stop
$200Frontier
Find Deal
Wed, Nov 26 - Thu, Dec 11
Frontier Logo
3:47 pm - 1:12 amMDW-SJU
7h 25m1 stop
Frontier Logo
3:00 pm - 11:25 pmSJU-MDW
10h 25m1 stop
$217Frontier
Find Deal
Wed, Dec 3 - Wed, Dec 10
Southwest Logo
10:40 am - 10:05 pmMDW-SJU
9h 25m1 stop
Southwest Logo
5:45 am - 1:45 pmSJU-MDW
10h 00m2 stops
$263Southwest
Find Deal
Thu, Dec 11 - Sun, Dec 14
Southwest Logo
1:10 pm - 10:05 pmMDW-SJU
6h 55m1 stop
Southwest Logo
6:40 am - 2:10 pmSJU-MDW
9h 30m2 stops
$289Southwest
Find Deal
Mon, Jan 19 - Fri, Jan 23
Delta Logo
6:00 am - 5:19 pmMDW-SJU
9h 19m1 stop
Delta Logo
6:15 am - 12:01 pmSJU-MDW
7h 46m1 stop
$321Delta
Find Deal
Tue, Nov 11 - Tue, Nov 18
Delta Logo
6:00 am - 3:38 pmMDW-PUJ
7h 38m1 stop
Delta Logo
3:50 pm - 11:40 pmPUJ-MDW
9h 50m1 stop
$338Delta
Find Deal
Mon, Oct 27 - Mon, Nov 3
Multiple Airlines Logo
5:28 pm - 11:42 amMDW-PUJ
17h 14m1 stop
Multiple Airlines Logo
4:25 pm - 11:38 amPUJ-MDW
21h 13m2 stops
$353Multiple Airlines
Find Deal
Fri, Oct 24 - Fri, Oct 31
Multiple Airlines Logo
5:28 pm - 11:28 amMDW-PUJ
17h 00m1 stop
Multiple Airlines Logo
3:57 pm - 6:39 pmPUJ-MDW
27h 42m2 stops
$355Multiple Airlines
Find Deal
Sun, Nov 16 - Sat, Nov 22
KLM Logo
6:00 am - 2:55 pmMDW-SXM
6h 55m1 stop
KLM Logo
3:30 pm - 11:40 pmSXM-MDW
10h 10m1 stop
$602KLM
Find Deal
Sun, Nov 16 - Sat, Nov 22
KLM Logo
6:00 am - 2:55 pmMDW-SXM
6h 55m1 stop
KLM Logo
3:30 pm - 8:54 amSXM-MDW
19h 24m2 stops
$606KLM
Find Deal
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 San Juan, at $666 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 $980.

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 $344, 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 May, when tickets cost $328 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $596 and $499 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Caribbean Islands?

The average price of all round-trip flights from Chicago Midway Airport to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Caribbean Islands on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Chicago Midway Airport to Caribbean Islands. For your return ticket, we recommend flying on a Friday and avoiding Saturdays for the best deals.

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 3 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$110
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly and prices are also 17% 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.

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

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $324 on average. Morning departures are around 45% more expensive than evening flights, 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 $519.

  • How many flights are there between Chicago Midway Airport and Caribbean Islands per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in Caribbean Islands, with an average flight time of 4h 40m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 1 flights.

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 4235 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

4.0 OkayAnnette, Oct 2025LGA - MCI
Read more Southwest reviews

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

The flight was an hour and a half late departing which was inconvenient

Delay in SLC jammed us up in Chicago. Got caught up in rush hour traffic

The crew took good care of us. The flight from ATL to SFO is a longer one, and there were multiple beverage offerings. I like the 757's that Delta uses. Good airplane that is comfortable. I do wish Delta would separate Priority boarding from the better seats. I would gladly take a smaller seat in an open row than be jammed into Comfort just to get priority boarding, just to make sure I don't have to check a bag.

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Gate agent rushed to fill hot jetway with crowd so it took over 12 minutes to go from gate to plane. Just like a discount airline Pooly prepared cabin and third time that claim of rough air prevented any cabin service. Friends on a Southwest flight at similar time had service.

Cramped seating for me. Luckily it wasn’t a long flight

Lounge in Lagos is terrible, food on board from Lagos to Atlanta was horrible. Only bright spot the cabin crew were awesome.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

I think Frontier was very good at communication. Their app worked very well. Loading was great and the flight was nice and easy.

This airline sucks. They offer low rates then charge you for everything, the app does not work well, the seats are the most uncomfortable. Maintenance issues on the flight, and you still have to sit through their credit card commercials. People are nice enough but does not make up for overall poor experience.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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