$116 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 7/6. 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$335
Santo Domingo
Santo Domingo1 stop$407
Montego Bay
Montego Bay1 stop$437
Oranjestad
Oranjestad1 stop$429
Nassau
Nassau1 stop$505
Kingston
Kingston1 stop$481
Simpson Bay
Simpson Bay1 stop$411
Providenciales
Providenciales1 stop$528
George Town
George Town1 stop$566
St. John's
St. John's3 stops$1,730
Aguadilla
Aguadilla1 stop$309

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
6:15 am - 2:47 pmMDW-SJU
7h 32m1 stop
Frontier Logo
6:00 am - 12:24 pmSJU-MDW
7h 24m1 stop
$294Frontier
Find Deal
Mon, May 5 - Thu, May 8
Frontier Logo
10:55 am - 12:05 amMDW-SJU
12h 10m1 stop
Frontier Logo
10:46 am - 11:39 pmSJU-MDW
13h 53m1 stop
$298Frontier
Find Deal
Sun, May 11 - Thu, May 15
Delta Logo
6:04 am - 1:15 pmMDW-PUJ
6h 11m1 stop
Delta Logo
2:40 pm - 10:22 pmPUJ-MDW
8h 42m1 stop
$335Delta
Find Deal
Sat, May 3 - Tue, May 6
Delta Logo
6:04 am - 3:32 pmMDW-PUJ
8h 28m1 stop
Delta Logo
2:40 pm - 10:22 pmPUJ-MDW
8h 42m1 stop
$364Delta
Find Deal
Sat, May 3 - Tue, May 6
Southwest Logo
6:35 am - 4:40 pmMDW-SJU
9h 05m1 stop
Southwest Logo
2:45 pm - 9:50 pmSJU-MDW
8h 05m1 stop
$381Southwest
Find Deal
Thu, Oct 2 - Wed, Oct 8
 Logo
2:53 pm - 11:07 pmMDW-SJU
7h 14m1 stop
 Logo
2:54 pm - 10:38 pmSJU-MDW
8h 44m1 stop
Wed, May 28 - Wed, Jun 4
Southwest Logo
2:55 pm - 11:15 pmMDW-SJU
7h 20m1 stop
Southwest Logo
5:50 pm - 1:05 amSJU-MDW
8h 15m1 stop
$401Southwest
Find Deal
Thu, Jun 12 - Mon, Jun 16
 Logo
1:19 pm - 11:47 amMDW-PUJ
21h 28m1 stop
 Logo
3:22 pm - 12:24 pmPUJ-MDW
22h 02m2 stops
Fri, May 9 - Wed, May 14
LATAM Airlines Logo
10:35 am - 5:40 pmMDW-AUA
30h 05m2 stops
LATAM Airlines Logo
6:50 pm - 6:03 pmAUA-MDW
24h 13m2 stops
$1,794LATAM Airlines
Find Deal
Sat, Aug 2 - Thu, Aug 7
LATAM Airlines Logo
1:05 pm - 5:40 pmMDW-AUA
27h 35m2 stops
LATAM Airlines Logo
6:50 pm - 9:51 amAUA-MDW
16h 01m2 stops
$1,968LATAM Airlines
Find Deal
Wed, Jul 30 - Mon, Aug 11

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 Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $518.

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 $417 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 $298 (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 $500 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

$116
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Chicago Midway Airport to Punta Cana

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 4287 reviews
8.6Crew
8.0Comfort
8.2Boarding
7.1Food
7.6Entertainment
Airline reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

8.0 ExcellentJonathan, Apr 2025AUS - MSY
Read more Southwest reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

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

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

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

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Easy boarding. Met expectations for a 2-3 hour flight. Early arrival at DFW caused a 39 minute delay on the tarmac in getting to our gate. 😏 overall, good flight.

Very efficient process and boarding, seats felt standard. Flight conditions from take off to landing had been very smooth. Alcohol on the menu however was not available… Will fly Spirit in the future for the price, you can’t really complain if you fly light.

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

My experience with Spirit went pretty much as expected. It's a no frills airline, and you get what you pay for. I don't require much, so I was grateful to have an inexpensive way to travel. It is sad to me that the gate agents and flight crew don't smile much or seem very friendly or helpful. They are competent and efficient, and that's really all I need.

My experience was okay. The flight did not offer even water without a fee. Also had to pay extra for my carry on, as I was told I had to check my bag, even though it said I had the option to carry on a bag when booking. This costed me an extra $100. Would likely not fly with Spirit again.

The flight was rescheduled several times without a reason for the schedule changes. I had to be in New Orleans at a certain time and it was just easier to drive at a certain point. I don’t know if the flight ever left. This is my first experience with Spirit Airlines and is also the last.

It was fast but uncomfortable seats. Had to pay a bit extra not sure why? Maybe in selection of all my 4 tix together ? Just knew I had a balance before getting boarding pass online when departing from satx ? And flight was delayed..

In a word, it was horrible. The flight crew timed out and this, apparently was not accounted for by management. This meant that our 10:15 departure turned into a 1:30am departure the next DAY!!! And some brainchild decided to email us 12$ food vouchers set to expire the 9th, but they sent them after EVERY VENDOR WAS CLOSED in the Miami airport and obviously none would be open in New Orleans. I found this to be another sterling example of, at best, shitty management…at worst an absolute lack of empathy for your customers. Triplt Pro: Check-in may be avail for NK222 dep MIA 4/8/2025 10:16pm. Conf#RGSUMI. https://tripit.com/t/. e106fd644e0a; Today 6:16 PM TripIt Pro: NK222 ON TIME. MIA dep 10:16pm term C, gate F5. MSY arr 11:38pm. Today 8:59 PM Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 2:18am. Alternate flights: https:// www.tripit.com/t/b2903869f438 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/834d176c630b Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/0441e41a9dd3 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:// www.tripit.com/t/92ac2157ef54 The sender is not in your contact

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

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!

Everything you need to know for your flight to Caribbean

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