$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 12/18. 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
$189
Overall average: $292
Multiple Airlines
Fri 12/5Sun 12/7
SJU - MDW • 2 stops
Cheapest non-stop
$464
Southwest
Wed 3/25Wed 4/1
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

Fri, Dec 5 - Sun, Dec 7
Multiple Airlines Logo
6:14 pm - 1:59 pmSJU-MDW
21h 45m2 stops
Multiple Airlines Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$189Multiple Airlines
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Wed, Dec 3 - Sun, Dec 7
Frontier Logo
7:10 am - 1:01 pmSJU-MDW
31h 51m1 stop
Frontier Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$194Frontier
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Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
4:10 am - 10:12 pmSJU-MDW
20h 02m2 stops
Multiple Airlines Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$203Multiple Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
1:59 am - 9:28 pmSJU-MDW
21h 29m2 stops
Frontier Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$206Frontier
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Thu, Dec 4 - Wed, Dec 10
Delta Logo
2:29 pm - 11:47 pmMBJ-MDW
10h 18m1 stop
Delta Logo
6:00 am - 1:04 pmMDW-MBJ
6h 04m1 stop
$334Delta
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Tue, Dec 2 - Tue, Dec 9
Delta Logo
1:06 pm - 11:47 pmNAS-MDW
11h 41m2 stops
Delta Logo
6:00 am - 1:30 pmMDW-NAS
6h 30m1 stop
$346Delta
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Mon, Dec 22 - Sat, Jan 10
Southwest Logo
3:25 pm - 10:25 pmMBJ-MDW
8h 00m1 stop
Southwest Logo
8:20 am - 1:15 pmMDW-MBJ
3h 55mnonstop
$368Southwest
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Mon, Dec 22 - Sat, Jan 10
Southwest Logo
3:25 pm - 11:50 pmMBJ-MDW
9h 25m2 stops
Southwest Logo
6:50 am - 2:40 pmMDW-MBJ
6h 50m1 stop
$413Southwest
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Fri, Dec 26 - Wed, Dec 31
WestJet Logo
4:20 pm - 5:19 pmSXM-MDW
50h 59m2 stops
WestJet Logo
9:50 am - 3:21 pmMDW-SXM
27h 31m2 stops
$3,116WestJet
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Wed, Dec 31 - Wed, Jan 7
WestJet Logo
4:20 pm - 11:06 amSXM-MDW
20h 46m2 stops
WestJet Logo
9:50 am - 3:21 pmMDW-SXM
27h 31m2 stops
$3,164WestJet
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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 4245 reviews
8.6Crew
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

10.0 ExcellentIlevba, Nov 2025DCA - DAL
Read more Southwest reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

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.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

the over had ligth did not work'd for the all way

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.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
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Saint Joseph
Hammond
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Chesterton
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Everything you need to know for your flight to Midway

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