$116 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 7/5. 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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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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Flights Deals

Best Caribbean Islands 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 Domingo2 stops$421
Montego Bay
Montego Bay1 stop$438
Oranjestad
Oranjestad1 stop$435
Nassau
Nassau1 stop$503
Kingston
Kingston1 stop$451
Simpson Bay
Simpson Bay1 stop$411
Providenciales
Providenciales1 stop$460
George Town
George Town1 stop$542
Aguadilla
Aguadilla1 stop$312
Punta Cana
Punta Cana1 stop$335
Santo Domingo
Santo Domingo2 stops$421
Montego Bay
Montego Bay1 stop$438
Oranjestad
Oranjestad1 stop$435
Nassau
Nassau1 stop$503
Kingston
Kingston1 stop$451
Simpson Bay
Simpson Bay1 stop$411
Providenciales
Providenciales1 stop$460
George Town
George Town1 stop$542
Aguadilla
Aguadilla1 stop$312

Cheap Flights from Midway to Caribbean Islands

 
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.

Recent round-trip flight deals from Midway to Caribbean Islands

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Caribbean Islands.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
10:55 am - 12:05 amMDW-SJU
12h 10m1 stop
Frontier Logo
3:56 am - 12:24 pmSJU-MDW
9h 28m1 stop
$298Frontier
Find Deal
Sun, May 11 - Wed, May 14
Frontier Logo
10:18 am - 3:26 pmMDW-SJU
28h 08m1 stop
Frontier Logo
3:14 pm - 8:47 amSJU-MDW
18h 33m1 stop
$303Frontier
Find Deal
Sun, Jun 1 - Fri, Jun 6
Delta Logo
6:00 am - 1:17 pmMDW-PUJ
6h 17m1 stop
Delta Logo
1:10 pm - 9:47 pmPUJ-MDW
9h 37m1 stop
$335Delta
Find Deal
Mon, Aug 11 - Fri, Aug 15
 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
 Logo
8:55 pm - 11:23 amMDW-SJU
13h 28m1 stop
 Logo
2:54 pm - 10:38 pmSJU-MDW
8h 44m1 stop
Fri, May 30 - Wed, Jun 4
Delta Logo
12:48 pm - 10:47 pmMDW-SJU
8h 59m1 stop
Delta Logo
6:15 am - 11:53 amSJU-MDW
6h 38m1 stop
$385Delta
Find Deal
Wed, May 14 - Sat, May 17
Southwest Logo
7:30 am - 2:55 pmMDW-SJU
6h 25m1 stop
Southwest Logo
7:20 am - 7:10 pmSJU-MDW
12h 50m2 stops
$397Southwest
Find Deal
Tue, Sep 16 - Tue, Sep 23
Southwest Logo
8:50 am - 2:35 pmMDW-SJU
4h 45mnonstop
Southwest Logo
4:15 pm - 11:00 pmSJU-MDW
7h 45m1 stop
$407Southwest
Find Deal
Sat, Jul 5 - Wed, Jul 9
LATAM Airlines Logo
4:22 pm - 5:45 pmMDW-AUA
24h 23m2 stops
LATAM Airlines Logo
6:50 pm - 11:53 amAUA-MDW
18h 03m2 stops
$2,337LATAM Airlines
Find Deal
Wed, Jul 30 - Mon, Aug 4
LATAM Airlines Logo
6:47 pm - 5:40 pmMDW-AUA
21h 53m2 stops
LATAM Airlines Logo
6:50 pm - 9:41 amAUA-MDW
15h 51m2 stops
$2,353LATAM Airlines
Find Deal
Fri, Aug 1 - Wed, Aug 6
Useful Info

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?

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 Islands.

The cheapest ticket to Caribbean Islands 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 $409.

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.

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 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 $299 (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 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.


Good to know

Low seasonNovember
High seasonMarch
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 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 27% 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 $456.

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 4293 reviews
7.1Food
8.0Comfort
8.6Crew
8.2Boarding
7.6Entertainment
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

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.

Flight was delayed due to weather. Crew did a nice job of making us comfortable. No complain complaints.

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

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.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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