$95 Find Cheap Flights from Caribbean Islands 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 2/25. 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
$180
Overall average: $401
Frontier
Thu 1/8Mon 1/12
SJU - MDW • 1 stop
Cheapest non-stop
$472
Southwest
Tue 3/17Tue 3/24
PUJ - MDW • Non-stop
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean Islands to Midway

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

Thu, Jan 8 - Mon, Jan 12
Frontier Logo
10:47 pm - 2:06 pm
SJU
-
MDW
17h 19m1 stop
Frontier Logo
4:31 pm - 2:50 am
MDW
-
SJU
8h 19m1 stop
$180Frontier
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
10:47 pm - 2:06 pm
SJU
-
MDW
17h 19m1 stop
Frontier Logo
4:31 pm - 2:50 am
MDW
-
SJU
8h 19m1 stop
$181Frontier
Fri, Jan 16 - Sun, Jan 18
Multiple Airlines Logo
6:00 am - 7:27 am
SJU
-
MDW
27h 27m2 stops
Multiple Airlines Logo
8:19 pm - 12:42 pm
MDW
-
SJU
14h 23m1 stop
$198Multiple 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
$321Multiple Airlines
Thu, Feb 5 - Thu, Feb 12
Delta Logo
4:45 pm - 10:22 pm
MBJ
-
MDW
6h 37m1 stop
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m1 stop
$443Delta
Thu, Feb 19 - Sat, Feb 21
Delta Logo
7:30 am - 5:45 pm
SDQ
-
MDW
12h 15m2 stops
Delta Logo
6:00 am - 3:30 pm
MDW
-
SDQ
7h 30m1 stop
$453Delta
Fri, Jan 16 - Sun, Jan 25
KLM Logo
4:35 pm - 10:07 pm
AUA
-
MDW
7h 32m1 stop
KLM Logo
6:14 pm - 12:55 pm
MDW
-
AUA
16h 41m1 stop
$460KLM
Fri, Jan 16 - Sun, Jan 25
Southwest Logo
3:20 pm - 10:25 pm
AUA
-
MDW
9h 05m1 stop
Southwest Logo
5:15 pm - 2:25 pm
MDW
-
AUA
19h 10m2 stops
$521Southwest
Fri, Jan 16 - Sun, Jan 25
Southwest Logo
3:20 pm - 5:05 am
AUA
-
MDW
15h 45m2 stops
Southwest Logo
5:15 pm - 2:25 pm
MDW
-
AUA
19h 10m2 stops
$551Southwest
Fri, Feb 6 - Fri, Feb 13
KLM Logo
1:55 pm - 10:22 pm
SXM
-
MDW
10h 27m1 stop
KLM Logo
7:20 pm - 2:15 pm
MDW
-
SXM
16h 55m1 stop
$604KLM
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$95
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from San Juan to Chicago Midway Airport

FAQs for booking Caribbean Islands to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Caribbean Islands 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 Islands 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 Islands 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 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 Caribbean Islands 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 Islands with another airline.

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

 
Need help choosing which airline to fly with from Caribbean Islands 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 4257 reviews
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

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.

10.0 ExcellentAnonymous, Dec 2025
DAL - CHS
Read more Southwest reviews

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.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

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)