$102 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 5/24. 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, Aug 20 - Mon, Aug 24
Southwest Logo
5:30 am - 2:55 pm
SJU
-
MDW
10h 25m
2 stops
Southwest Logo
2:55 pm - 11:50 pm
MDW
-
SJU
7h 55m
1 stop
$226Southwest
Mon, Aug 17 - Sun, Aug 23
Southwest Logo
6:30 am - 1:45 pm
SJU
-
MDW
8h 15m
2 stops
Southwest Logo
8:05 am - 5:05 pm
MDW
-
SJU
8h 00m
1 stop
$246Southwest
Wed, Aug 5 - Tue, Aug 18
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
6:05 am - 4:37 pm
MDW
-
SJU
9h 32m
1 stop
$256Delta
Wed, Aug 5 - Fri, Aug 14
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
12:46 pm - 10:29 pm
MDW
-
SJU
8h 43m
1 stop
$266Delta
Wed, Oct 21 - Wed, Oct 28
Frontier Logo
3:51 pm - 9:58 pm
SJU
-
MDW
7h 07m
1 stop
Frontier Logo
7:25 am - 3:25 pm
MDW
-
SJU
7h 00m
1 stop
$276Frontier
Sat, May 23 - Tue, May 26
Frontier Logo
6:25 am - 2:12 pm
SJU
-
MDW
8h 47m
1 stop
Frontier Logo
3:07 pm - 4:49 am
MDW
-
SJU
12h 42m
1 stop
$281Frontier
Wed, Aug 5 - Mon, Aug 17
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
6:05 am - 1:42 pm
MDW
-
SJU
6h 37m
1 stop
$286Delta
Thu, Aug 27 - Sun, Sep 20
Southwest Logo
5:00 am - 11:45 am
SJU
-
MDW
7h 45m
1 stop
Southwest Logo
7:10 am - 5:05 pm
MDW
-
SJU
8h 55m
2 stops
$296Southwest
Mon, Jun 29 - Wed, Jul 8
Multiple Airlines Logo
3:05 pm - 9:40 am
AUA
-
MDW
19h 35m
1 stop
Multiple Airlines Logo
3:20 pm - 2:15 pm
MDW
-
AUA
21h 55m
1 stop
$606Multiple Airlines
Mon, Jun 29 - Tue, Jul 7
Multiple Airlines Logo
3:05 pm - 9:40 am
AUA
-
MDW
19h 35m
1 stop
Multiple Airlines Logo
3:20 pm - 2:15 pm
MDW
-
AUA
21h 55m
1 stop
$628Multiple Airlines
Useful Info

Good to know

Low seasonDecember
Cheapest flight$102
Best time to beat the crowds with an average 7% 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.

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
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)