$97 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 2/4. 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
$170
Typical prices: $302-$448
Frontier
Wed 2/4Mon 2/9
SJU - MDW • 1 stop
Cheapest non-stop
$420
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

Wed, Feb 4 - Mon, Feb 9
Frontier Logo
4:36 pm - 7:52 pm
SJU
-
MDW
29h 16m1 stop
Frontier Logo
1:00 pm - 12:57 pm
MDW
-
SJU
21h 57m1 stop
$170Frontier
Thu, Feb 19 - Thu, Feb 26
Frontier Logo
6:00 am - 2:26 pm
SJU
-
MDW
10h 26m1 stop
Frontier Logo
6:15 am - 12:39 pm
MDW
-
SJU
28h 24m1 stop
$171Frontier
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
$336Multiple Airlines
Wed, Feb 18 - Wed, Feb 25
Multiple Airlines Logo
1:01 pm - 1:56 pm
PUJ
-
MDW
26h 55m1 stop
Multiple Airlines Logo
7:00 am - 4:36 pm
MDW
-
PUJ
31h 36m2 stops
$340Multiple Airlines
Sat, Feb 21 - Sat, Feb 28
Delta Logo
4:44 pm - 10:31 pm
MBJ
-
MDW
6h 47m1 stop
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m1 stop
$401Delta
Thu, Jan 22 - Mon, Jan 26
Delta Logo
2:56 pm - 10:22 pm
NAS
-
MDW
8h 26m1 stop
Delta Logo
10:46 am - 5:02 pm
MDW
-
NAS
5h 16m1 stop
$441Delta
Thu, Apr 30 - Sun, May 3
Southwest Logo
1:05 pm - 11:40 pm
GCM
-
MDW
10h 35m1 stop
Southwest Logo
5:05 am - 11:55 am
MDW
-
GCM
6h 50m1 stop
$465Southwest
Thu, Apr 30 - Sun, May 3
Southwest Logo
1:05 pm - 11:55 pm
GCM
-
MDW
10h 50m2 stops
Southwest Logo
5:05 am - 11:55 am
MDW
-
GCM
6h 50m1 stop
$470Southwest
Sun, Feb 22 - Sun, Mar 1
WestJet Logo
2:50 pm - 5:37 pm
GCM
-
MDW
27h 47m2 stops
WestJet Logo
9:50 am - 1:44 pm
MDW
-
GCM
26h 54m2 stops
$1,217WestJet
Thu, Feb 26 - Sat, Feb 28
WestJet Logo
4:30 pm - 11:03 am
AUA
-
MDW
44h 33m2 stops
WestJet Logo
5:00 pm - 3:35 pm
MDW
-
AUA
44h 35m2 stops
$3,513WestJet
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$97
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 San Juan 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 4249 reviews
7.5Entertainment
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
Airline reviews

Never went on board this flight. Kayak uses Underpricer (which is a scam business) as it's "customer service provider". This customer service is a classic bait and switch "service". I Got caught in the UnderPricer Bait and switch scam. 14 hours on the phone with people from India with heavy accents and upselling me to useless products. The original sell was a flight on spirit. Then they contact me later, an say after they have my money that the flight is no good as is is only one seat for a party of two. I am still in dispute to get my money back. Went to Spirit direct and had a beautiful vacation. I should never have used Kayak and their rip off artists UnderPricer.

2.0 MediocreAnonymous, Jan 2026
SJU - BWI
Read more Southwest reviews

Never went on board this flight. Kayak uses Underpricer (which is a scam business) as it's "customer service provider". This customer service is a classic bait and switch "service". I Got caught in the UnderPricer Bait and switch scam. 14 hours on the phone with people from India with heavy accents and upselling me to useless products. The original sell was a flight on spirit. Then they contact me later, an say after they have my money that the flight is no good as is is only one seat for a party of two. I am still in dispute to get my money back. Went to Spirit direct and had a beautiful vacation. I should never have used Kayak and their rip off artists UnderPricer.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

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.

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)