$110 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 4/21. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Useful Info
Flight Deals

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

Thu, May 7 - Sun, May 10
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
9:14 am - 10:48 pm
MDW
-
SJU
12h 34m
1 stop
$202Frontier
Fri, May 8 - Mon, May 11
Frontier Logo
3:19 pm - 4:13 pm
SJU
-
MDW
25h 54m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$213Frontier
Thu, Apr 30 - Mon, May 4
Frontier Logo
3:21 am - 10:28 am
SJU
-
MDW
8h 07m
1 stop
Frontier Logo
8:41 am - 2:01 am
MDW
-
SJU
16h 20m
1 stop
$214Frontier
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
$223Frontier
Fri, May 8 - Tue, May 12
Southwest Logo
6:50 am - 6:10 pm
SJU
-
MDW
12h 20m
1 stop
Southwest Logo
12:50 pm - 10:40 pm
MDW
-
SJU
8h 50m
2 stops
$246Southwest
Tue, May 5 - Tue, May 12
Multiple Airlines Logo
6:10 am - 1:00 pm
SDQ
-
MDW
7h 50m
1 stop
Multiple Airlines Logo
2:20 pm - 4:29 pm
MDW
-
SDQ
25h 09m
2 stops
$352Multiple Airlines
Tue, May 5 - Tue, May 12
Multiple Airlines Logo
6:10 am - 1:00 pm
SDQ
-
MDW
7h 50m
1 stop
Multiple Airlines Logo
7:30 am - 5:29 am
MDW
-
SDQ
20h 59m
1 stop
$354Multiple Airlines
Wed, Apr 1 - Tue, Apr 7
Delta Logo
6:10 pm - 10:31 pm
NAS
-
MDW
5h 21m
1 stop
Delta Logo
6:00 am - 4:45 pm
MDW
-
NAS
9h 45m
1 stop
$465Delta
Fri, May 1 - Sun, May 31
Delta Logo
4:00 pm - 10:14 am
NAS
-
MDW
19h 14m
2 stops
Delta Logo
6:23 am - 4:35 pm
MDW
-
NAS
9h 12m
1 stop
$475Delta
Mon, Apr 13 - Mon, Apr 20
Southwest Logo
1:05 pm - 12:05 am
GCM
-
MDW
11h 00m
1 stop
Southwest Logo
5:35 am - 12:10 pm
MDW
-
GCM
6h 35m
1 stop
$510Southwest
Useful Info

Good to know

Low seasonMarch
Cheapest flight$110
Most popular time to fly and prices are also 25% lower on average.
Flight from Aguadilla 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 airline 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 4303 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

2.0 MediocreAnonymous, Feb 2026
BWI - PBI
Read more Southwest reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

Great plane, great attendants,great flight crew,on time. Wonderful flight home..

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

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
Munster
Schererville
Porter
Monticello
Griffith
Saint John

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)