$95 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 3/5. 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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Everything you should know

Cheapest round-trip
$198
Overall average: $448
Multiple Airlines
Wed 2/25Sun 3/1
SJU - MDW • 2 stops
Cheapest non-stop
$411
Southwest
Fri 3/6Tue 3/10
PUJ - MDW • Non-stop
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We hope you love your trip to Midway!
Flight Deals
Useful Info
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

Wed, Feb 25 - Sun, Mar 1
Multiple Airlines Logo
4:31 pm - 4:16 pm
SJU
-
MDW
25h 45m
2 stops
Multiple Airlines Logo
6:15 am - 2:09 am
MDW
-
SJU
17h 54m
1 stop
$198Multiple Airlines
Fri, May 8 - Mon, May 11
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$202Frontier
Thu, Mar 5 - Mon, Mar 9
Frontier Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
Frontier Logo
6:00 am - 9:03 pm
MDW
-
SJU
14h 03m
1 stop
$205Frontier
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
Multiple Airlines Logo
6:00 am - 5:58 pm
MDW
-
SJU
10h 58m
1 stop
$206Multiple Airlines
Thu, Feb 26 - Mon, Mar 2
Frontier Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
Frontier Logo
9:22 pm - 9:54 am
MDW
-
SJU
10h 32m
1 stop
$207Frontier
Thu, Apr 16 - Mon, Apr 20
Delta Logo
3:57 pm - 10:28 pm
PUJ
-
MDW
7h 31m
1 stop
Delta Logo
6:00 am - 1:21 pm
MDW
-
PUJ
6h 21m
1 stop
$380Delta
Thu, Apr 16 - Mon, Apr 20
Southwest Logo
2:05 pm - 10:45 pm
PUJ
-
MDW
9h 40m
2 stops
Southwest Logo
9:15 pm - 1:05 pm
MDW
-
PUJ
14h 50m
2 stops
$430Southwest
Fri, Mar 13 - Tue, Mar 17
Delta Logo
1:15 pm - 5:54 pm
NAS
-
MDW
5h 39m
1 stop
Delta Logo
6:00 am - 11:53 am
MDW
-
NAS
4h 53m
1 stop
$485Delta
Thu, Apr 23 - Sun, May 3
Southwest Logo
2:35 pm - 11:40 pm
SXM
-
MDW
10h 05m
1 stop
Southwest Logo
5:05 am - 2:25 pm
MDW
-
SXM
8h 20m
1 stop
$546Southwest
Thu, Mar 26 - Thu, Apr 2
WestJet Logo
3:20 pm - 12:29 pm
SXM
-
MDW
22h 09m
2 stops
WestJet Logo
1:10 pm - 2:17 pm
MDW
-
SXM
24h 07m
2 stops
$3,706WestJet
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$95
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 21% 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 4283 reviews
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
Airline reviews

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

2.0 MediocreMike, Feb 2026
LAS - OKC
Read more Southwest reviews

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

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

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

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