$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
$210
Overall average: $299
Frontier
Thu 12/4Mon 12/8
SJU - MDW • 1 stop
Cheapest non-stop
$379
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

Thu, Dec 4 - Mon, Dec 8
Frontier Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
Frontier Logo
8:42 pm - 6:23 pmMDW-SJU
19h 41m2 stops
$210Frontier
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Thu, Dec 4 - Mon, Dec 8
Frontier Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
Frontier Logo
6:15 am - 3:11 pmMDW-SJU
6h 56m1 stop
$216Frontier
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Fri, Dec 5 - Mon, Dec 8
Delta Logo
7:00 am - 11:55 amSJU-MDW
6h 55m1 stop
Delta Logo
6:00 am - 2:14 pmMDW-SJU
6h 14m1 stop
$227Delta
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Thu, Dec 4 - Thu, Dec 11
Multiple Airlines Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
Multiple Airlines Logo
2:16 pm - 7:50 pmMDW-SJU
27h 34m1 stop
$250Multiple Airlines
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Wed, Jan 21 - Sun, Jan 25
Southwest Logo
9:05 am - 6:35 pmSJU-MDW
11h 30m1 stop
Southwest Logo
1:35 pm - 12:05 amMDW-SJU
8h 30m2 stops
$252Southwest
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Thu, Feb 19 - Tue, Feb 24
Southwest Logo
7:00 am - 6:30 pmSJU-MDW
13h 30m1 stop
Southwest Logo
8:25 am - 5:05 pmMDW-SJU
6h 40m1 stop
$267Southwest
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Fri, Dec 5 - Sun, Dec 7
Delta Logo
6:38 pm - 11:47 pmSJU-MDW
7h 09m1 stop
Delta Logo
10:49 am - 11:20 pmMDW-SJU
10h 31m1 stop
$272Delta
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Wed, Dec 24 - Wed, Dec 31
Multiple Airlines Logo
6:08 pm - 5:38 pmPUJ-MDW
25h 30m2 stops
Multiple Airlines Logo
6:12 am - 10:27 amMDW-PUJ
26h 15m1 stop
$306Multiple Airlines
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Wed, Dec 3 - Sun, Dec 7
WestJet Logo
4:30 pm - 1:10 pmAUA-MDW
22h 40m2 stops
WestJet Logo
1:50 pm - 3:40 pmMDW-AUA
23h 50m2 stops
$962WestJet
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Thu, Nov 20 - Tue, Nov 25
WestJet Logo
2:50 pm - 9:53 amGCM-MDW
44h 03m2 stops
WestJet Logo
10:47 am - 1:44 pmMDW-GCM
49h 57m2 stops
$1,314WestJet
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Useful Info

Good to know

Low seasonFebruary
Cheapest flight$110
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 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 4236 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

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

8.0 ExcellentTODD, Oct 2025CMH - HOU
Read more Southwest reviews

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.

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!

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!

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Crew blocked exits to front of ship with galley carts. Also split five person family apart on international flight without fixing.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

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

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