$137 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 6/3. 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.
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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.

Recent round-trip flight deals from Caribbean Islands to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Caribbean Islands to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
6:00 am - 5:30 pmSJU-MDW
12h 30m1 stop
Frontier Logo
1:19 pm - 10:01 pmMDW-SJU
7h 42m1 stop
$298Frontier
Find Deal
Sun, May 11 - Fri, May 16
Frontier Logo
3:56 am - 12:24 pmSJU-MDW
9h 28m1 stop
Frontier Logo
12:15 pm - 1:50 amMDW-SJU
12h 35m1 stop
$299Frontier
Find Deal
Thu, May 15 - Mon, May 19
Delta Logo
2:39 pm - 9:47 pmSJU-MDW
8h 08m1 stop
Delta Logo
6:00 am - 4:50 pmMDW-SJU
9h 50m1 stop
$391Delta
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Thu, Aug 28 - Tue, Sep 2
Southwest Logo
1:20 pm - 10:30 pmSJU-MDW
10h 10m1 stop
Southwest Logo
7:30 am - 2:55 pmMDW-SJU
6h 25m1 stop
$397Southwest
Find Deal
Thu, Sep 11 - Tue, Sep 16
Southwest Logo
5:50 am - 2:00 pmSJU-MDW
9h 10m2 stops
Southwest Logo
6:05 am - 3:10 pmMDW-SJU
8h 05m1 stop
$418Southwest
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Thu, Aug 28 - Mon, Sep 1
Delta Logo
1:06 pm - 9:41 pmSJU-MDW
9h 35m1 stop
Delta Logo
6:00 am - 4:50 pmMDW-SJU
9h 50m1 stop
$429Delta
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Fri, Aug 8 - Mon, Aug 11
 Logo
9:08 am - 10:44 pmMBJ-MDW
13h 36m1 stop
 Logo
5:36 pm - 11:02 amMDW-MBJ
17h 26m2 stops
Tue, Jun 3 - Tue, Jun 10
 Logo
12:07 pm - 10:28 pmMBJ-MDW
10h 21m2 stops
 Logo
6:20 am - 2:43 pmMDW-MBJ
8h 23m1 stop
Sat, Jun 14 - Sat, Jun 21
WestJet Logo
10:30 am - 5:40 pmMBJ-MDW
31h 10m2 stops
WestJet Logo
12:44 pm - 9:27 amMDW-MBJ
20h 43m2 stops
$1,054WestJet
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Sat, Jun 14 - Sat, Jun 21
WestJet Logo
2:45 pm - 9:51 amPUJ-MDW
20h 06m2 stops
WestJet Logo
3:40 pm - 1:43 pmMDW-PUJ
21h 03m2 stops
$3,908WestJet
Find Deal
Tue, Aug 19 - Tue, Aug 26
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Good to know

Low seasonFebruary
High seasonNovember
Cheapest flight$137
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 1% lower on average.
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.

Top 3 airlines serving 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 4294 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
8.6Crew
7.1Food
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Fine except the person next to me took up her seat had raised the arm divide so she spilled into my seat. because of her size. Fortunately no one was in the seat on my right so I could use part of it.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

I guess you get what you pay for. The seats are very uncomfortable and very little space. The snacks were pricey.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

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