$110 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 12/24. 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
$217
Overall average: $294
Frontier
Tue 12/23Sat 1/3
SJU - MDW • 1 stop
Cheapest non-stop
$472
Southwest
Sat 11/22Sat 11/29
PUJ - MDW • Non-stop
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Flight Deals
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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

Tue, Dec 23 - Sat, Jan 3
Frontier Logo
3:54 am - 2:37 pmSJU-MDW
12h 43m1 stop
Frontier Logo
2:24 pm - 2:39 amMDW-SJU
10h 15m1 stop
$217Frontier
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Thu, Dec 18 - Wed, Jan 7
Frontier Logo
3:54 am - 9:19 amSJU-MDW
31h 25m1 stop
Frontier Logo
3:52 pm - 1:42 amMDW-SJU
7h 50m1 stop
$237Frontier
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Fri, Dec 5 - Sun, Dec 7
Southwest Logo
11:20 am - 7:35 pmSJU-MDW
10h 15m2 stops
Southwest Logo
2:20 pm - 1:25 amMDW-SJU
9h 05m1 stop
$265Southwest
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Thu, Dec 11 - Mon, Dec 15
Multiple Airlines Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
Multiple Airlines Logo
8:42 pm - 11:25 pmMDW-SJU
24h 43m2 stops
$268Multiple Airlines
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Mon, Dec 8 - Mon, Dec 15
Multiple Airlines Logo
10:42 am - 8:46 amSJU-MDW
24h 04m2 stops
Multiple Airlines Logo
3:52 pm - 11:25 pmMDW-SJU
29h 33m1 stop
$274Multiple Airlines
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Fri, Jan 23 - Tue, Feb 3
Delta Logo
6:15 am - 12:01 pmSJU-MDW
7h 46m1 stop
Delta Logo
12:48 pm - 8:57 pmMDW-SJU
6h 09m1 stop
$335Delta
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Fri, Dec 5 - Mon, Dec 8
Southwest Logo
9:40 am - 7:30 pmSJU-MDW
11h 50m1 stop
Southwest Logo
6:40 am - 6:35 pmMDW-SJU
9h 55m2 stops
$336Southwest
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Sat, Jan 24 - Sat, Jan 31
Delta Logo
4:55 pm - 10:26 pmPUJ-MDW
7h 31m1 stop
Delta Logo
6:00 am - 3:30 pmMDW-PUJ
7h 30m1 stop
$344Delta
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Fri, Jan 9 - Mon, Jan 12
WestJet Logo
8:25 pm - 11:05 amMBJ-MDW
15h 40m2 stops
WestJet Logo
11:21 am - 1:54 pmMDW-MBJ
25h 33m2 stops
$1,160WestJet
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Fri, Dec 26 - Fri, Jan 2
WestJet Logo
4:50 pm - 11:06 amNAS-MDW
19h 16m2 stops
WestJet Logo
9:50 am - 5:12 pmMDW-NAS
30h 22m2 stops
$1,532WestJet
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Useful Info

Good to know

Low seasonFebruary
Cheapest flight$110
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 airlines 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 4238 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

8.0 ExcellentTODD, Nov 2025DAL - CMH
Read more Southwest reviews

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

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.

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

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.

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

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