$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 9/13. 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

Thu, Sep 18 - Thu, Sep 25
 Logo
7:05 am - 6:43 pmSJU-MDW
12h 38m1 stop
 Logo
1:49 pm - 12:43 amMDW-SJU
9h 54m1 stop
Fri, Oct 24 - Fri, Oct 31
Frontier Logo
3:40 am - 10:21 amSJU-MDW
7h 41m1 stop
Frontier Logo
6:20 am - 2:19 pmMDW-SJU
6h 59m1 stop
$240Frontier
Find Deal
Fri, Oct 24 - Fri, Oct 31
Frontier Logo
3:40 am - 10:21 amSJU-MDW
7h 41m1 stop
Frontier Logo
6:20 am - 2:19 pmMDW-SJU
6h 59m1 stop
$244Frontier
Find Deal
Thu, Sep 18 - Mon, Sep 22
 Logo
7:05 am - 6:43 pmSJU-MDW
12h 38m1 stop
 Logo
5:15 pm - 1:58 amMDW-SJU
31h 43m2 stops
Thu, Oct 2 - Wed, Oct 8
Southwest Logo
1:05 pm - 9:55 pmSJU-MDW
9h 50m1 stop
Southwest Logo
6:55 am - 5:15 pmMDW-SJU
9h 20m1 stop
$327Southwest
Find Deal
Fri, Sep 19 - Tue, Sep 23
Delta Logo
12:50 pm - 9:47 amMBJ-MDW
20h 57m2 stops
Delta Logo
6:00 am - 1:09 pmMDW-MBJ
7h 09m1 stop
$344Delta
Find Deal
Thu, Oct 2 - Tue, Oct 7
Delta Logo
2:35 pm - 8:40 amMBJ-MDW
18h 05m2 stops
Delta Logo
6:00 am - 12:07 pmMDW-MBJ
6h 07m1 stop
$345Delta
Find Deal
Wed, Oct 1 - Mon, Oct 6
Southwest Logo
2:50 pm - 9:40 pmPUJ-MDW
7h 50m1 stop
Southwest Logo
5:00 am - 2:30 pmMDW-PUJ
8h 30m1 stop
$369Southwest
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Fri, Nov 28 - Fri, Dec 5
WestJet Logo
4:50 pm - 1:07 pmNAS-MDW
21h 17m2 stops
WestJet Logo
10:35 am - 5:12 pmMDW-NAS
29h 37m2 stops
$1,442WestJet
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Fri, Oct 31 - Sun, Nov 2
WestJet Logo
4:50 pm - 1:08 pmNAS-MDW
21h 18m2 stops
WestJet Logo
10:40 am - 3:50 pmMDW-NAS
28h 10m2 stops
$3,088WestJet
Find Deal
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$137
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly and prices are also 13% 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 airline 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 4242 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

2.0 MediocreMike, Aug 2025AUS - BWI
Read more Southwest reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Valparaiso
Lansing
Chesterton
Munster
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

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