$123 Find Cheap Flights from Caribbean 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 9/20. 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 to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean 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 to Midway

Wed, Oct 1 - Mon, Oct 6
Frontier Logo
12:28 am - 7:11 amSJU-MDW
7h 43m1 stop
Frontier Logo
6:20 am - 2:11 pmMDW-SJU
6h 51m1 stop
$271Frontier
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Thu, Sep 4 - Sun, Sep 14
Frontier Logo
12:28 am - 7:11 amSJU-MDW
7h 43m1 stop
Frontier Logo
6:20 am - 2:11 pmMDW-SJU
6h 51m1 stop
$278Frontier
Find Deal
Fri, Sep 12 - Sat, Sep 20
Frontier Logo
3:39 am - 9:51 amSJU-MDW
7h 12m1 stop
Frontier Logo
6:15 am - 2:11 pmMDW-SJU
6h 56m1 stop
$284Frontier
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Fri, Oct 10 - Mon, Oct 13
 Logo
3:19 pm - 3:11 pmSJU-MDW
24h 52m1 stop
 Logo
5:28 pm - 2:12 pmMDW-SJU
19h 44m1 stop
Wed, Oct 8 - Tue, Oct 14
 Logo
2:49 am - 9:47 amSJU-MDW
7h 58m1 stop
 Logo
8:05 am - 12:45 amMDW-SJU
15h 40m2 stops
Sat, Nov 8 - Sat, Nov 15
Southwest Logo
2:20 pm - 5:35 pmSJU-MDW
5h 15mnonstop
Southwest Logo
8:40 am - 5:25 pmMDW-SJU
6h 45m1 stop
$347Southwest
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Sat, Sep 13 - Sat, Sep 20
Southwest Logo
7:45 am - 3:35 pmSJU-MDW
8h 50m2 stops
Southwest Logo
9:40 am - 7:25 pmMDW-SJU
8h 45m1 stop
$351Southwest
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Wed, Sep 10 - Mon, Sep 15
Delta Logo
2:47 pm - 9:26 pmSDQ-MDW
7h 39m1 stop
Delta Logo
6:00 am - 1:24 pmMDW-SDQ
6h 24m1 stop
$450Delta
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Fri, Jan 30 - Sun, Feb 8
Delta Logo
3:40 pm - 9:46 pmSDQ-MDW
8h 06m1 stop
Delta Logo
6:00 am - 2:15 pmMDW-SDQ
6h 15m1 stop
$452Delta
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Wed, Oct 1 - Wed, Oct 8
Air Transat Logo
3:05 pm - 4:24 pmPUJ-MDW
26h 19m2 stops
Air Transat Logo
9:35 am - 1:45 pmMDW-PUJ
27h 10m2 stops
$641Air Transat
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Good to know

Low seasonFebruary
Cheapest flight$123
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 to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Caribbean 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 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 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 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 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean 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 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 to Midway

 
Need help choosing which airline to fly with from Caribbean 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 4246 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

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.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

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.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

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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