$80 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 11/2. 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

Wed, Aug 6 - Mon, Aug 25
Frontier Logo
8:15 am - 7:36 pmSJU-MDW
12h 21m1 stop
Frontier Logo
6:15 am - 2:26 pmMDW-SJU
7h 11m1 stop
$220Frontier
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Thu, Oct 2 - Mon, Oct 6
Frontier Logo
3:16 pm - 11:20 pmSJU-MDW
9h 04m1 stop
Frontier Logo
8:29 am - 11:52 pmMDW-SJU
14h 23m1 stop
$232Frontier
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Thu, Sep 25 - Sun, Sep 28
Delta Logo
12:58 pm - 9:36 pmSJU-MDW
9h 38m1 stop
Delta Logo
6:00 am - 1:16 pmMDW-SJU
6h 16m1 stop
$233Delta
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Thu, Sep 11 - Tue, Sep 16
Southwest Logo
4:05 pm - 10:00 pmSJU-MDW
6h 55m1 stop
Southwest Logo
7:30 am - 2:55 pmMDW-SJU
6h 25m1 stop
$265Southwest
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Sat, Sep 13 - Tue, Sep 16
Southwest Logo
2:20 pm - 8:45 pmSJU-MDW
7h 25m1 stop
Southwest Logo
1:25 pm - 10:45 pmMDW-SJU
8h 20m2 stops
$292Southwest
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Fri, Nov 21 - Sun, Nov 23
Delta Logo
3:30 pm - 9:44 pmSJU-MDW
8h 14m1 stop
Delta Logo
1:05 pm - 11:17 pmMDW-SJU
8h 12m1 stop
$312Delta
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Thu, Sep 11 - Mon, Sep 15
 Logo
1:20 pm - 4:43 pmSDQ-MDW
28h 23m3 stops
 Logo
12:50 pm - 1:55 amMDW-SDQ
12h 05m2 stops
Thu, Sep 11 - Mon, Sep 15
 Logo
1:20 pm - 4:43 pmSDQ-MDW
28h 23m3 stops
 Logo
12:50 pm - 12:15 pmMDW-SDQ
22h 25m3 stops
Wed, Oct 29 - Wed, Nov 5
WestJet Logo
3:50 pm - 1:09 pmNAS-MDW
22h 19m2 stops
WestJet Logo
9:20 am - 2:57 pmMDW-NAS
28h 37m2 stops
$3,101WestJet
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Tue, Aug 19 - Sun, Aug 24
WestJet Logo
11:15 am - 5:37 pmNAS-MDW
31h 22m2 stops
WestJet Logo
7:17 pm - 10:23 amMDW-NAS
38h 06m2 stops
$3,246WestJet
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Good to know

Low seasonFebruary
High seasonNovember
Cheapest flight$80
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.

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 4252 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.6Entertainment
Airline reviews

It was one and half hour late... Not sure if any other experience matters.

4.0 OkaySudhir, Jul 2025LGA - MCI
Read more Southwest reviews

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

Leaving on time and having my luggage on my connecting flight

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

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