$121 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 4/10. 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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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, May 1 - Fri, May 8
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
4:52 pm - 2:08 am
MDW
-
SJU
8h 16m
1 stop
$176Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
6:00 am - 2:13 pm
MDW
-
SJU
7h 13m
1 stop
$186Frontier
Fri, Apr 17 - Mon, Apr 20
Frontier Logo
3:19 pm - 4:00 pm
SJU
-
MDW
25h 41m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$192Frontier
Fri, Apr 17 - Mon, Apr 20
Frontier Logo
3:19 pm - 4:00 pm
SJU
-
MDW
25h 41m
1 stop
Frontier Logo
9:14 am - 2:06 pm
MDW
-
SJU
27h 52m
1 stop
$196Frontier
Fri, Apr 17 - Mon, Apr 20
Delta Logo
2:10 pm - 10:28 pm
MBJ
-
MDW
8h 18m
1 stop
Delta Logo
6:00 am - 12:54 pm
MDW
-
MBJ
6h 54m
1 stop
$407Delta
Sun, Apr 19 - Sat, Apr 25
Multiple Airlines Logo
2:38 am - 10:19 pm
BQN
-
MDW
20h 41m
2 stops
Multiple Airlines Logo
9:14 am - 1:43 am
MDW
-
BQN
15h 29m
1 stop
$421Multiple Airlines
Fri, Apr 17 - Mon, Apr 20
Southwest Logo
12:15 pm - 8:15 pm
MBJ
-
MDW
8h 00m
2 stops
Southwest Logo
7:30 am - 1:55 pm
MDW
-
MBJ
6h 25m
1 stop
$436Southwest
Mon, Apr 27 - Wed, Apr 29
Multiple Airlines Logo
10:19 am - 10:19 pm
SDQ
-
MDW
13h 00m
2 stops
Multiple Airlines Logo
7:30 am - 4:30 pm
MDW
-
SDQ
8h 00m
1 stop
$440Multiple Airlines
Thu, Apr 30 - Mon, May 4
Southwest Logo
1:05 pm - 11:55 pm
GCM
-
MDW
10h 50m
2 stops
Southwest Logo
5:35 am - 12:10 pm
MDW
-
GCM
6h 35m
1 stop
$476Southwest
Fri, Jul 10 - Wed, Jul 15
Delta Logo
6:04 pm - 10:15 pm
NAS
-
MDW
5h 11m
1 stop
Delta Logo
6:05 am - 4:39 pm
MDW
-
NAS
9h 34m
1 stop
$511Delta
Useful Info

Good to know

Low seasonDecember
Cheapest flight$119
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 22% 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 4344 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

4.0 Okaysangeetha, Apr 2026
AUS - SJC
Read more Southwest reviews

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I am very please with the service received from Southwest. Although there was a refuel stop in Fl before we got the Baltimore. The service and kindness of the staff was excellent.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

Traveling to a place near Midway?

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

Everything you need to know for your flight to Midway

Information on your arrival and departure airports