$96 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 3/4. 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
$188
Overall average: $425
Frontier
Fri 2/27Mon 3/2
SJU - MDW • 1 stop
Cheapest non-stop
$559
Southwest
Tue 3/10Tue 3/17
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 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

Fri, Feb 27 - Mon, Mar 2
Frontier Logo
3:53 am - 2:55 pm
SJU
-
MDW
13h 02m
1 stop
Frontier Logo
9:22 pm - 9:54 am
MDW
-
SJU
10h 32m
1 stop
$188Frontier
Wed, Apr 8 - Thu, Apr 9
Frontier Logo
1:11 pm - 10:19 pm
SJU
-
MDW
10h 08m
1 stop
Frontier Logo
2:56 pm - 12:52 am
MDW
-
SJU
8h 56m
1 stop
$202Frontier
Fri, Mar 6 - Tue, Mar 10
Multiple Airlines Logo
6:50 pm - 1:41 pm
SJU
-
MDW
20h 51m
1 stop
Multiple Airlines Logo
6:00 am - 5:58 pm
MDW
-
SJU
10h 58m
2 stops
$212Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
Frontier Logo
4:11 pm - 10:29 pm
SJU
-
MDW
8h 18m
1 stop
Frontier Logo
6:05 am - 2:17 pm
MDW
-
SJU
7h 12m
1 stop
$220Frontier
Fri, Mar 6 - Tue, Mar 10
Multiple Airlines Logo
6:50 pm - 1:41 pm
SJU
-
MDW
20h 51m
1 stop
Multiple Airlines Logo
6:00 am - 4:32 pm
MDW
-
SJU
9h 32m
1 stop
$228Multiple Airlines
Thu, Mar 5 - Wed, Mar 11
Delta Logo
12:20 pm - 5:45 pm
MBJ
-
MDW
6h 25m
1 stop
Delta Logo
6:00 am - 3:28 pm
MDW
-
MBJ
9h 28m
1 stop
$307Delta
Tue, Mar 10 - Tue, Mar 17
Delta Logo
3:50 pm - 10:31 pm
PUJ
-
MDW
7h 41m
1 stop
Delta Logo
6:00 am - 3:40 pm
MDW
-
PUJ
8h 40m
1 stop
$369Delta
Wed, Feb 11 - Wed, Feb 18
Southwest Logo
2:00 pm - 9:00 pm
MBJ
-
MDW
8h 00m
1 stop
Southwest Logo
5:00 am - 1:00 pm
MDW
-
MBJ
7h 00m
1 stop
$380Southwest
Thu, Mar 5 - Wed, Mar 11
Southwest Logo
1:25 pm - 8:15 pm
NAS
-
MDW
7h 50m
1 stop
Southwest Logo
6:00 am - 12:30 pm
MDW
-
NAS
5h 30m
1 stop
$506Southwest
Fri, Mar 27 - Fri, Apr 3
WestJet Logo
3:20 pm - 1:25 pm
SXM
-
MDW
23h 05m
2 stops
WestJet Logo
9:35 am - 2:17 pm
MDW
-
SXM
51h 42m
2 stops
$3,242WestJet
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$96
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 13% increase in price.
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 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 4280 reviews
8.6Crew
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
Airline reviews

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.

10.0 ExcellentCarol, Feb 2026
DEN - MSP
Read more Southwest reviews

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.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

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