$97 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 2/11. 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.

Everything you should know

Cheapest round-trip
$176
Overall average: $445
Frontier
Tue 3/10Wed 3/25
SJU - MDW • 1 stop
Cheapest non-stop
$420
Southwest
Wed 3/25Wed 4/1
PUJ - MDW • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
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

Tue, Mar 10 - Wed, Mar 25
Frontier Logo
3:22 pm - 10:19 pm
SJU
-
MDW
7h 57m1 stop
Frontier Logo
6:00 am - 2:12 pm
MDW
-
SJU
7h 12m1 stop
$176Frontier
Wed, Mar 11 - Tue, Mar 17
Frontier Logo
3:22 pm - 10:19 pm
SJU
-
MDW
7h 57m1 stop
Frontier Logo
11:19 am - 8:54 am
MDW
-
SJU
20h 35m1 stop
$177Frontier
Thu, Feb 26 - Mon, Mar 2
Frontier Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m1 stop
Frontier Logo
9:22 pm - 9:54 am
MDW
-
SJU
10h 32m1 stop
$182Frontier
Wed, Feb 18 - Wed, Feb 25
Multiple Airlines Logo
1:01 pm - 1:56 pm
PUJ
-
MDW
26h 55m1 stop
Multiple Airlines Logo
7:00 am - 4:36 pm
MDW
-
PUJ
31h 36m2 stops
$340Multiple Airlines
Wed, Feb 11 - Wed, Feb 18
Multiple Airlines Logo
1:01 pm - 1:56 pm
PUJ
-
MDW
26h 55m1 stop
Multiple Airlines Logo
7:00 am - 11:02 am
MDW
-
PUJ
26h 02m2 stops
$341Multiple Airlines
Thu, Feb 12 - Wed, Feb 18
Delta Logo
2:10 pm - 10:31 pm
AUA
-
MDW
10h 21m1 stop
Delta Logo
6:40 pm - 12:55 pm
MDW
-
AUA
16h 15m1 stop
$450Delta
Wed, Feb 25 - Wed, Mar 4
Delta Logo
3:42 pm - 10:31 pm
SDQ
-
MDW
8h 49m1 stop
Delta Logo
10:49 am - 12:32 am
MDW
-
SDQ
11h 43m2 stops
$454Delta
Thu, Apr 30 - Sun, May 3
Southwest Logo
1:05 pm - 11:40 pm
GCM
-
MDW
10h 35m1 stop
Southwest Logo
5:05 am - 11:55 am
MDW
-
GCM
6h 50m1 stop
$465Southwest
Thu, Apr 30 - Sun, May 3
Southwest Logo
1:05 pm - 11:55 pm
GCM
-
MDW
10h 50m2 stops
Southwest Logo
8:55 pm - 12:10 pm
MDW
-
GCM
15h 15m2 stops
$470Southwest
Wed, Feb 25 - Wed, Mar 4
WestJet Logo
7:35 pm - 12:46 pm
AUA
-
MDW
19h 11m2 stops
WestJet Logo
1:29 pm - 3:35 pm
MDW
-
AUA
24h 06m2 stops
$3,152WestJet
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$97
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 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 4253 reviews
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

10.0 ExcellentDaniel, Jan 2026
BWI - MHT
Read more Southwest reviews

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

Never went on board this flight. Kayak uses Underpricer (which is a scam business) as it's "customer service provider". This customer service is a classic bait and switch "service". I Got caught in the UnderPricer Bait and switch scam. 14 hours on the phone with people from India with heavy accents and upselling me to useless products. The original sell was a flight on spirit. Then they contact me later, an say after they have my money that the flight is no good as is is only one seat for a party of two. I am still in dispute to get my money back. Went to Spirit direct and had a beautiful vacation. I should never have used Kayak and their rip off artists UnderPricer.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

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