$99 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 1/23. 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
$180
Overall average: $325
Frontier
Thu 2/26Mon 3/2
SJU - MDW • 1 stop
Cheapest non-stop
$452
Southwest
Sat 5/9Sat 5/16
PUJ - MDW • Non-stop
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Flight Deals
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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

Thu, Feb 26 - Mon, Mar 2
Frontier Logo
4:11 pm - 11:25 pmSJU-MDW
9h 14m1 stop
Frontier Logo
8:56 pm - 9:55 amMDW-SJU
10h 59m1 stop
$180Frontier
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Thu, Mar 5 - Mon, Mar 9
Frontier Logo
9:37 pm - 9:58 pmSJU-MDW
26h 21m1 stop
Frontier Logo
8:00 am - 12:45 amMDW-SJU
15h 45m1 stop
$181Frontier
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Thu, Jan 22 - Sun, Jan 25
Delta Logo
2:15 pm - 10:22 pmSJU-MDW
10h 07m1 stop
Delta Logo
6:00 am - 5:17 pmMDW-SJU
9h 17m1 stop
$225Delta
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Fri, Jan 23 - Tue, Feb 3
Delta Logo
3:55 pm - 10:22 pmSJU-MDW
8h 27m1 stop
Delta Logo
6:00 am - 2:31 pmMDW-SJU
6h 31m1 stop
$226Delta
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Mon, Jan 26 - Mon, Feb 2
Multiple Airlines Logo
5:47 pm - 12:05 pmPUJ-MDW
20h 18m2 stops
Multiple Airlines Logo
1:00 pm - 6:00 pmMDW-PUJ
27h 00m1 stop
$318Multiple Airlines
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Thu, Dec 25 - Thu, Jan 1
Multiple Airlines Logo
11:37 am - 5:38 pmPUJ-MDW
8h 01m1 stop
Multiple Airlines Logo
6:33 pm - 4:50 pmMDW-PUJ
20h 17m2 stops
$320Multiple Airlines
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Sun, Dec 21 - Sun, Jan 4
Southwest Logo
3:25 pm - 11:50 pmMBJ-MDW
9h 25m2 stops
Southwest Logo
5:30 am - 2:25 pmMDW-MBJ
7h 55m1 stop
$401Southwest
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Sun, Dec 21 - Sun, Jan 4
Southwest Logo
3:25 pm - 11:50 pmMBJ-MDW
9h 25m2 stops
Southwest Logo
5:20 am - 2:55 pmMDW-MBJ
8h 35m2 stops
$441Southwest
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Wed, Jan 14 - Wed, Jan 21
WestJet Logo
4:20 pm - 1:09 pmSXM-MDW
22h 49m2 stops
WestJet Logo
1:49 pm - 3:21 pmMDW-SXM
23h 32m2 stops
$3,152WestJet
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Mon, Dec 22 - Thu, Jan 15
WestJet Logo
4:20 pm - 5:19 pmSXM-MDW
26h 59m2 stops
WestJet Logo
9:50 am - 3:21 pmMDW-SXM
27h 31m2 stops
$3,237WestJet
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Good to know

Low seasonFebruary
Cheapest flight$99
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Aguadilla 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 airlines 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
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
Airline reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

10.0 ExcellentDavid, Nov 2025BUF - PHX
Read more Southwest reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

One of the best airlines that I flew on, the flight attendants were very attentive and professional.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

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

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