$108 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 12/25. 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
$203
Overall average: $299
Frontier
Wed 12/24Sat 1/3
SJU - MDW • 1 stop
Cheapest non-stop
$455
Southwest
Wed 3/25Wed 4/1
PUJ - MDW • Non-stop
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Flight Deals
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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, Dec 24 - Sat, Jan 3
Frontier Logo
7:30 am - 10:12 pmSJU-MDW
16h 42m1 stop
Frontier Logo
2:24 pm - 2:39 amMDW-SJU
10h 15m1 stop
$203Frontier
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Fri, Dec 5 - Mon, Dec 8
Frontier Logo
4:31 pm - 10:12 pmSJU-MDW
7h 41m1 stop
Frontier Logo
6:15 am - 3:11 pmMDW-SJU
6h 56m1 stop
$211Frontier
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Sat, Jan 31 - Thu, Feb 5
Southwest Logo
5:30 am - 12:10 pmSJU-MDW
8h 40m1 stop
Southwest Logo
6:10 am - 9:50 pmMDW-SJU
13h 40m1 stop
$252Southwest
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Fri, Nov 21 - Sun, Nov 23
Multiple Airlines Logo
12:37 pm - 7:31 pmSJU-MDW
8h 54m1 stop
Multiple Airlines Logo
8:04 pm - 3:53 pmMDW-SJU
17h 49m1 stop
$256Multiple Airlines
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Thu, Nov 20 - Mon, Nov 24
Multiple Airlines Logo
12:37 pm - 7:31 pmSJU-MDW
8h 54m1 stop
Multiple Airlines Logo
5:47 pm - 10:49 amMDW-SJU
15h 02m1 stop
$259Multiple Airlines
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Thu, Jan 15 - Sun, Jan 18
Southwest Logo
7:00 am - 12:55 pmSJU-MDW
7h 55m1 stop
Southwest Logo
8:25 am - 5:05 pmMDW-SJU
6h 40m1 stop
$277Southwest
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Thu, Dec 4 - Sat, Dec 6
Delta Logo
3:10 pm - 9:54 amAUA-MDW
20h 44m2 stops
Delta Logo
1:50 pm - 1:55 pmMDW-AUA
22h 05m2 stops
$339Delta
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Sun, Dec 7 - Thu, Dec 11
Delta Logo
2:55 pm - 11:47 pmNAS-MDW
9h 52m1 stop
Delta Logo
6:00 am - 3:43 pmMDW-NAS
8h 43m1 stop
$344Delta
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Wed, Dec 3 - Sun, Dec 7
WestJet Logo
7:35 pm - 1:10 pmAUA-MDW
19h 35m2 stops
WestJet Logo
9:59 am - 3:40 pmMDW-AUA
27h 41m2 stops
$801WestJet
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Fri, Nov 21 - Sat, Nov 29
WestJet Logo
5:30 pm - 1:07 pmAUA-MDW
21h 37m3 stops
WestJet Logo
9:41 am - 3:40 pmMDW-AUA
27h 59m3 stops
$1,039WestJet
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Useful Info

Good to know

Low seasonFebruary
Cheapest flight$108
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 6% 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 3 airlines serving 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 4240 reviews
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

2.0 MediocreAnonymous, Nov 2025ORD - LAS
Read more Southwest reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

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.

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

DELTA does a terrific job making sure you are well taken care of during the flight, gives you assurance before the flight through numerous email notifications about your upcoming flight & lastly good follow up after the flight making sure your needs were mat. It has been, is & will continue to be my carrier of choice in all my future travels. Good Job DELTA

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

Seats comfortable, service and food very mediocre, staff not very attentive, worse than many other our flights with Delta.

Overall good experience; however, there was one flight attendant who was rather rough compared to everyone else. Everything else was good: entertainment, food. Delta keeps on delivering! Thank you!

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

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.

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
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Everything you need to know for your flight to Midway

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