$123 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 4/24. 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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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, Apr 30 - Sat, May 2
Frontier Logo
3:21 am - 10:28 am
SJU
-
MDW
8h 07m
1 stop
Frontier Logo
9:14 am - 10:48 pm
MDW
-
SJU
12h 34m
1 stop
$176Frontier
Sat, May 2 - Sun, May 3
Frontier Logo
7:00 am - 4:13 pm
SJU
-
MDW
10h 13m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$186Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
8:41 am - 2:01 am
MDW
-
SJU
16h 20m
1 stop
$187Frontier
Thu, May 7 - Mon, May 11
Frontier Logo
3:03 am - 3:57 pm
SJU
-
MDW
13h 54m
1 stop
Frontier Logo
4:52 pm - 2:08 am
MDW
-
SJU
8h 16m
1 stop
$196Frontier
Thu, Jul 30 - Mon, Aug 3
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
$328Southwest
Thu, Jul 30 - Mon, Aug 3
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
Southwest Logo
5:10 am - 10:45 am
MDW
-
MBJ
5h 35m
1 stop
$373Southwest
Wed, Apr 22 - Sat, Apr 25
Multiple Airlines Logo
2:35 pm - 1:00 pm
SDQ
-
MDW
23h 25m
2 stops
Multiple Airlines Logo
7:30 am - 5:29 am
MDW
-
SDQ
20h 59m
1 stop
$382Multiple Airlines
Fri, May 8 - Fri, May 15
Multiple Airlines Logo
2:40 pm - 11:04 am
PUJ
-
MDW
21h 24m
2 stops
Multiple Airlines Logo
4:52 pm - 9:18 am
MDW
-
PUJ
15h 26m
1 stop
$386Multiple Airlines
Wed, Jun 24 - Mon, Jul 6
Delta Logo
1:21 pm - 10:17 pm
MBJ
-
MDW
8h 56m
1 stop
Delta Logo
6:58 pm - 3:34 pm
MDW
-
MBJ
20h 36m
2 stops
$414Delta
Thu, May 21 - Wed, May 27
Delta Logo
1:15 pm - 9:09 pm
AUA
-
MDW
8h 54m
1 stop
Delta Logo
5:12 pm - 12:00 pm
MDW
-
AUA
17h 48m
1 stop
$541Delta
Useful Info

Good to know

Low seasonDecember
Cheapest flight$123
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 4338 reviews
7.5Entertainment
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
Airline reviews

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

6.0 GoodKenley, Apr 2026
AUS - LAS
Read more Southwest reviews

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

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.

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