$117 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 12/6. 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.
1 adult
1 adult, Economy

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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, Nov 5 - Mon, Nov 10
Frontier Logo
3:59 am - 9:12 amSJU-MDW
7h 13m1 stop
Frontier Logo
6:15 am - 3:14 pmMDW-SJU
6h 59m1 stop
$212Frontier
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Fri, Nov 14 - Tue, Nov 18
Frontier Logo
10:39 pm - 10:26 amSJU-MDW
13h 47m1 stop
Frontier Logo
6:26 pm - 3:33 amMDW-SJU
31h 07m1 stop
$225Frontier
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Thu, Dec 4 - Fri, Dec 5
Multiple Airlines Logo
3:00 pm - 11:25 pmSJU-MDW
10h 25m1 stop
Multiple Airlines Logo
8:42 pm - 5:33 pmMDW-SJU
18h 51m2 stops
$252Multiple Airlines
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Thu, Jan 22 - Mon, Feb 2
Southwest Logo
5:40 am - 1:10 pmSJU-MDW
9h 30m2 stops
Southwest Logo
6:50 am - 7:05 pmMDW-SJU
10h 15m2 stops
$263Southwest
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Thu, Feb 5 - Thu, Feb 19
Southwest Logo
5:35 am - 12:30 pmSJU-MDW
8h 55m2 stops
Southwest Logo
6:10 am - 9:50 pmMDW-SJU
13h 40m1 stop
$300Southwest
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Sat, Nov 1 - Sat, Nov 8
Multiple Airlines Logo
9:38 am - 9:22 pmPUJ-MDW
12h 44m1 stop
Multiple Airlines Logo
2:05 pm - 12:08 pmMDW-PUJ
20h 03m2 stops
$305Multiple Airlines
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Thu, Jan 15 - Mon, Jan 19
Delta Logo
2:55 pm - 9:46 pmNAS-MDW
7h 51m1 stop
Delta Logo
6:00 am - 1:30 pmMDW-NAS
6h 30m1 stop
$336Delta
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Fri, Nov 21 - Tue, Nov 25
Delta Logo
2:55 pm - 11:40 pmNAS-MDW
9h 45m1 stop
Delta Logo
6:00 am - 3:26 pmMDW-NAS
8h 26m1 stop
$344Delta
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Fri, Nov 28 - Fri, Dec 5
WestJet Logo
4:50 pm - 1:07 pmNAS-MDW
21h 17m2 stops
WestJet Logo
9:59 am - 5:12 pmMDW-NAS
30h 13m3 stops
$1,452WestJet
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Fri, Nov 28 - Fri, Dec 5
WestJet Logo
4:50 pm - 1:07 pmNAS-MDW
21h 17m3 stops
WestJet Logo
9:59 am - 5:12 pmMDW-NAS
30h 13m3 stops
$1,482WestJet
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Everything you should know

Cheapest round-trip
$212
Overall average: $284
Frontier
Wed 11/5Mon 11/10
SJU - MDW • 1 stop
Cheapest non-stop
$370
Southwest
Sat 12/20Sat 1/3
MBJ - MDW • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$117
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 2% 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 airlines 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 4239 reviews
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

2.0 MediocreThomas, Oct 2025SAT - STL
Read more Southwest reviews

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

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
Munster
Chesterton
Schererville
Porter
Monticello
Saint John
Griffith

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