$91 Find Cheap Flights from Caribbean to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 2/5. 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.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$181
Overall average: $501
Frontier
Thu 1/22Mon 1/26
SJU - MDW • 1 stop
Cheapest non-stop
$437
Southwest
Wed 3/25Wed 4/1
PUJ - MDW • Non-stop
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We hope you love your trip to Midway!
Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to Midway 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 Caribbean to Midway

Thu, Jan 22 - Mon, Jan 26
Frontier Logo
4:22 pm - 10:19 pm
SJU
-
MDW
7h 57m1 stop
Frontier Logo
1:00 pm - 11:59 pm
MDW
-
SJU
8h 59m1 stop
$181Frontier
Thu, Jan 22 - Mon, Jan 26
Frontier Logo
4:22 pm - 10:19 pm
SJU
-
MDW
7h 57m1 stop
Frontier Logo
1:00 pm - 11:59 pm
MDW
-
SJU
8h 59m1 stop
$182Frontier
Fri, Feb 13 - Fri, Feb 20
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m1 stop
Multiple Airlines Logo
7:30 am - 8:25 pm
MDW
-
PUJ
10h 55m1 stop
$319Multiple Airlines
Fri, Feb 20 - Fri, Feb 27
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m1 stop
Multiple Airlines Logo
7:30 am - 8:25 pm
MDW
-
PUJ
10h 55m1 stop
$325Multiple Airlines
Sat, Jan 17 - Tue, Feb 17
Delta Logo
3:46 pm - 10:07 pm
SDQ
-
MDW
8h 21m1 stop
Delta Logo
1:28 pm - 12:32 am
MDW
-
SDQ
9h 04m2 stops
$432Delta
Tue, Feb 17 - Tue, Feb 24
Delta Logo
4:44 pm - 10:33 pm
MBJ
-
MDW
6h 49m1 stop
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m1 stop
$447Delta
Thu, Feb 12 - Wed, Feb 18
Southwest Logo
3:25 pm - 10:45 pm
AUA
-
MDW
9h 20m1 stop
Southwest Logo
5:00 am - 2:25 pm
MDW
-
AUA
7h 25m1 stop
$489Southwest
Thu, Jan 22 - Sat, Jan 31
KLM Logo
2:10 pm - 10:22 pm
AUA
-
MDW
10h 12m1 stop
KLM Logo
4:30 pm - 12:30 pm
MDW
-
AUA
18h 00m1 stop
$491KLM
Fri, May 1 - Sat, May 9
Southwest Logo
12:35 pm - 10:20 pm
MBJ
-
MDW
9h 45m1 stop
Southwest Logo
6:10 am - 1:30 pm
MDW
-
MBJ
7h 20m1 stop
$504Southwest
Sat, Jan 31 - Sat, Feb 7
KLM Logo
5:28 pm - 9:53 am
SXM
-
MDW
18h 25m1 stop
KLM Logo
6:25 am - 4:03 pm
MDW
-
SXM
7h 38m1 stop
$635KLM
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$91
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Aguadilla to Chicago Midway Airport

FAQs for booking Caribbean to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Caribbean to Chicago Midway Airport?

    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 Caribbean to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from 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 Caribbean to Chicago Midway Airport?

    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 to Chicago Midway Airport with an airline and back to Caribbean with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean to Chicago Midway Airport?

    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 to Chicago Midway Airport from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Caribbean to Midway

 
Need help choosing which airline to fly with from Caribbean to Midway? 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 4252 reviews
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

Pretty seamless, just a tad bit late in taking off and landing.

8.0 ExcellentSudhir, Jan 2026
MCI - LGA
Read more Southwest reviews

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)