$116 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 4/16. 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 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, Apr 16 - Sun, Apr 19
Frontier Logo
3:19 pm - 7:59 am
SJU
-
MDW
17h 40m
1 stop
Frontier Logo
9:04 am - 2:01 am
MDW
-
SJU
15h 57m
1 stop
$202Frontier
Thu, Apr 30 - Mon, May 4
Frontier Logo
3:03 pm - 10:19 pm
SJU
-
MDW
8h 16m
1 stop
Frontier Logo
8:41 am - 2:01 am
MDW
-
SJU
16h 20m
1 stop
$213Frontier
Fri, Apr 24 - Sun, Apr 26
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$222Frontier
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
Tue, Apr 21 - Tue, Apr 28
Multiple Airlines Logo
9:38 am - 10:14 pm
PUJ
-
MDW
13h 36m
2 stops
Multiple Airlines Logo
7:30 am - 4:19 pm
MDW
-
PUJ
7h 49m
1 stop
$364Multiple Airlines
Tue, Apr 21 - Tue, Apr 28
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
$365Multiple Airlines
Sat, May 23 - Sat, Jun 13
Southwest Logo
11:35 am - 3:45 pm
MBJ
-
MDW
4h 10mnonstop
Southwest Logo
10:10 am - 2:00 pm
MDW
-
MBJ
3h 50mnonstop
$381Southwest
Sat, May 23 - Sat, Jun 13
Southwest Logo
11:35 am - 3:45 pm
MBJ
-
MDW
4h 10mnonstop
Southwest Logo
5:15 am - 12:40 pm
MDW
-
MBJ
7h 25m
1 stop
$404Southwest
Fri, Apr 17 - Mon, Apr 20
Delta Logo
3:28 pm - 10:28 pm
NAS
-
MDW
8h 00m
1 stop
Delta Logo
6:00 am - 4:33 pm
MDW
-
NAS
9h 33m
1 stop
$485Delta
Mon, Apr 27 - Tue, May 5
Delta Logo
5:58 pm - 10:28 pm
NAS
-
MDW
5h 30m
1 stop
Delta Logo
6:00 am - 2:03 pm
MDW
-
NAS
7h 03m
1 stop
$515Delta
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Good to know

Low seasonMarch
Cheapest flight$116
Most popular time to fly and prices are also 24% lower on average.
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 4317 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

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

Chicago Midway Airport (MDW)