$93 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 6/25. 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

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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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean Islands to Midway

Fri, Jul 11 - Mon, Jul 14
Frontier Logo
7:55 am - 5:35 pmSJU-MDW
10h 40m1 stop
Frontier Logo
8:35 am - 2:39 amMDW-SJU
17h 04m1 stop
$203Frontier
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Thu, Jul 10 - Mon, Jul 14
Frontier Logo
12:59 am - 11:51 pmSJU-MDW
23h 52m1 stop
Frontier Logo
8:35 am - 2:39 amMDW-SJU
17h 04m1 stop
$212Frontier
Find Deal
Fri, Jul 11 - Tue, Jul 15
Southwest Logo
11:25 am - 7:45 pmSJU-MDW
9h 20m1 stop
Southwest Logo
11:15 am - 9:15 pmMDW-SJU
9h 00m1 stop
$327Southwest
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Thu, Sep 11 - Tue, Sep 16
Delta Logo
12:55 pm - 9:44 pmSJU-MDW
9h 49m1 stop
Delta Logo
6:00 am - 4:08 pmMDW-SJU
9h 08m1 stop
$331Delta
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Tue, Jul 29 - Fri, Aug 8
Southwest Logo
3:45 pm - 7:35 pmPUJ-MDW
4h 50mnonstop
Southwest Logo
5:10 am - 2:05 pmMDW-PUJ
7h 55m1 stop
$332Southwest
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Tue, Aug 19 - Tue, Aug 26
Delta Logo
2:40 pm - 9:49 pmPUJ-MDW
8h 09m1 stop
Delta Logo
6:00 am - 1:15 pmMDW-PUJ
6h 15m1 stop
$341Delta
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Thu, Jun 26 - Mon, Jun 30
 Logo
8:24 pm - 2:03 pmSJU-MDW
18h 39m2 stops
 Logo
10:34 am - 7:19 pmMDW-SJU
31h 45m2 stops
Wed, Jul 23 - Mon, Jul 28
 Logo
1:37 am - 2:04 pmSJU-MDW
37h 27m3 stops
 Logo
9:12 am - 1:35 amMDW-SJU
39h 23m3 stops
Mon, Aug 11 - Mon, Aug 18
WestJet Logo
12:25 pm - 1:03 pmAUA-MDW
25h 38m2 stops
WestJet Logo
9:15 am - 1:55 pmMDW-AUA
27h 40m2 stops
$3,064WestJet
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Tue, Aug 5 - Tue, Aug 26
WestJet Logo
12:25 pm - 1:06 pmPUJ-MDW
25h 41m2 stops
WestJet Logo
1:43 pm - 11:28 amMDW-PUJ
20h 45m2 stops
$3,630WestJet
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Good to know

Low seasonFebruary
High seasonNovember
Cheapest flight$93
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 11% 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 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 4278 reviews
8.2Boarding
8.0Comfort
7.6Entertainment
8.6Crew
7.1Food
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

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.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

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