$135 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 4/9. 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.
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Best Caribbean Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$326
Santo Domingo
Santo Domingo1 stop$411
Montego Bay
Montego Bay1 stop$422
Oranjestad
Oranjestad1 stop$468
Nassau
Nassau1 stop$441
Kingston
Kingston1 stop$472
Simpson Bay
Simpson Bay1 stop$431
Providenciales
Providenciales1 stop$528
George Town
George Town1 stop$522
Aguadilla
Aguadilla1 stop$306

Cheap Flight Deals from Midway to Caribbean (MDW-0CB)

 
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.

Recent round-trip flight deals from Midway to Caribbean

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Caribbean.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Frontier Logo
3:00 pm - 10:53 pmMDW-SJU
6h 53m1 stop
Frontier Logo
2:45 am - 9:24 amSJU-MDW
7h 39m1 stop
$292Frontier
Find Deal
Wed, Apr 16 - Sat, Apr 19
Frontier Logo
12:15 pm - 1:50 amMDW-SJU
12h 35m1 stop
Frontier Logo
6:00 am - 12:24 pmSJU-MDW
7h 24m1 stop
$294Frontier
Find Deal
Mon, May 5 - Fri, May 9
Delta Logo
6:04 am - 2:30 pmMDW-PUJ
7h 26m1 stop
Delta Logo
2:47 pm - 9:28 pmPUJ-MDW
7h 41m1 stop
$326Delta
Find Deal
Mon, May 5 - Wed, May 14
Delta Logo
6:00 am - 1:22 pmMDW-PUJ
6h 22m1 stop
Delta Logo
1:05 pm - 9:28 pmPUJ-MDW
9h 23m1 stop
$335Delta
Find Deal
Wed, May 7 - Wed, May 14
Southwest Logo
6:35 am - 6:50 pmMDW-SJU
11h 15m1 stop
Southwest Logo
8:00 am - 5:35 pmSJU-MDW
10h 35m2 stops
$381Southwest
Find Deal
Sat, Apr 26 - Tue, Apr 29
Southwest Logo
8:30 am - 8:15 pmMDW-SJU
10h 45m2 stops
Southwest Logo
8:00 am - 6:25 pmSJU-MDW
11h 25m1 stop
$388Southwest
Find Deal
Tue, Apr 22 - Tue, Apr 29
 Logo
1:19 pm - 1:05 pmMDW-PUJ
22h 46m2 stops
 Logo
2:59 pm - 11:47 pmPUJ-MDW
9h 48m1 stop
Fri, May 2 - Mon, May 5
 Logo
9:12 pm - 11:47 amMDW-PUJ
13h 35m1 stop
 Logo
12:42 pm - 8:17 pmPUJ-MDW
8h 35m1 stop
Sun, May 25 - Fri, May 30
WestJet Logo
9:20 am - 1:15 pmMDW-SXM
26h 55m2 stops
WestJet Logo
2:10 pm - 5:45 pmSXM-MDW
28h 35m2 stops
$1,420WestJet
Find Deal
Wed, May 7 - Sun, May 11
WestJet Logo
1:16 pm - 2:35 pmMDW-AUA
24h 19m3 stops
WestJet Logo
3:30 pm - 2:22 pmAUA-MDW
23h 52m3 stops
$1,955WestJet
Find Deal
Mon, Apr 14 - Sun, Apr 20

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Caribbean.
The cheapest ticket to Caribbean from Chicago Midway Airport found in the last 72 hours was to San Juan, at $376 round-trip. The most popular route is from Chicago Midway Airport (MDW) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $376.

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 at night, when round-trip flights cost $324 on average. Morning departures are around 27% more expensive than evening flights, 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 $456.

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.
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $408 on average.

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 May, when tickets cost $258 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $604 and $479 respectively.

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

The average price of all round-trip flights from Chicago Midway Airport to Caribbean clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Caribbean on a Tuesday and more expensive on a Saturday. On your return trip to Chicago Midway Airport, you should consider flying back on a Friday, and avoid Saturdays for better deals.

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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low season

November

High season

March

Cheapest flight

$135
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 6% 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.

See more FAQs

Top 4 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 4272 reviews
8.2Boarding
7.6Entertainment
8.0Comfort
8.6Crew
7.1Food
Airline reviews

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

6.0 GoodCarolynn, Mar 2025KOA - SMF
Read more Southwest reviews

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Short flight with plenty of open seats. Drinks and snacks were still provided even on such a short flight. <1 hr

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

Very good. Sad to learn Southwest is going start to charge for bags

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

WiFi on the flight was not working. Thus, entertainment options were limited.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

After a 5 hour delay waiting at the gate (3 delays adding up) with no clear reason provided, we finally boarded flew 3/4 of the way to Toronto then were turned back to New York. As we neared New York, the pilot declared that it was his fault, something to do with timing and him not being allowed into the country???? How could the airline let his happen? They had hours to prepare and make sure they had a crew available for the flight! We ended up in Toronto a day late with no sleep.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Friendly flight attendants, smooth 8-9 hours flight. Economy seats are small and uncomfortable as usual.

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Bathrooms dirty sinks clogged. No one seemed to clean them. Plane very old

I book a filght for me and my daughter from Miami home to Las Vegas and getting her checked in was awful the lady at the baggage check in was horrible!!! She was the rudest person I have ever encountered in my entire life!!!! My daughter dose not speak Spanish and so I was trying to translate for her but the woman would not let me so my daughter was 100 💯 confused because she could not understand what was going on or being said at all horrible absolutely horrible and rude extremely stressful worst experience ever!!!!!!! And then we were actually told by other air port staff not to complain because if we did sprint would make sure we miss our flight ✈️ that they do it all the time 😧

Terrible! They kept postponing and finally canceled our flight. They canceled so late. We had no other options but to drive to a different city and try to find a new flight to get onto our cruise. We still aren’t there yet and might not make it.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

The flight was on time. The seats are very narrow.

My only complaint is that the standing recline. I wasn’t aware of that when I booked the ticket.

Unclear pricing; ended up being charged an extra $52 just to get onboard

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

No leg room AT all extremely uncomfortable flight water even cost 5 dollars

Seats are poor. They do not lean back. They do not even have pockets on the back, making it impossible to store a phone or a coke bottle. If you opt for basic economy cheap seats, they stick you always in the middle or window seat, even though there are unoccupied seats on the aisle. And then there is the nickel and diming. No carry-ons. And checking your carry-on is $70. At the end there is no price advantage but there is plenty of aggravation.

Not good. No updates regarding the flight status until after the fact on the delays and then a cancellation.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Landing in terminal 2, but my luggage is terminal 3. We (and others) were looking for it in terminal 1. We probably missed the crew broadcast, but the communication could have been clearer for non native (or elderly) passengers.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

Bag should not be so much money. This is how Frontier takes advantage of customers

The plane was comfortable. The time to board was way too slow and very unorganized! The crew was not as friendly as normally. The was not a single time that they offered water nor anything!!!

They switched my flight to Spirit, Never using Kayak again,

i was denied boarding, even though i had an assigned seat, checked in on line and was at airport early. Then they refused to fully refund the the fair and replacement fair because they claimed it was "no show/denied boarding". I will never fly this airline again

I was not permitted on my flight and had to purchase another flight ticket to Las Vegas.

This was a full flight and I was in Zone 1, however upon boarding, several other zones went in ahead of me, leaving no overhead cabin space near my seat. This created a challenging disembarkment process.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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