$108 Find Cheap Flights from Chicago Midway Airport to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Caribbean Islands departing on 5/5. 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 Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$301
Santo Domingo
Santo Domingo1 stop$390
Montego Bay
Montego Bay1 stop$308
Oranjestad
Oranjestad1 stop$547
Nassau
Nassau1 stop$494
Kingston
Kingston1 stop$556
Simpson Bay
Simpson Bay1 stop$515
Providenciales
Providenciales1 stop$475
George Town
George Town2 stops$507
St. John's
St. John's1 stop$929
Aguadilla
Aguadilla1 stop$256
Punta Cana
Punta Cana2 stops$301
Santo Domingo
Santo Domingo1 stop$390
Montego Bay
Montego Bay1 stop$308
Oranjestad
Oranjestad1 stop$547
Nassau
Nassau1 stop$494
Kingston
Kingston1 stop$556
Simpson Bay
Simpson Bay1 stop$515
Providenciales
Providenciales1 stop$475
George Town
George Town2 stops$507
St. John's
St. John's1 stop$929
Aguadilla
Aguadilla1 stop$256

Book Cheap Midway to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Caribbean Islands 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 Midway to Caribbean Islands

Fri, Apr 17 - Fri, Apr 17
Frontier Logo
9:14 am - 10:48 pm
MDW
-
SJU
12h 34m
1 stop
Frontier Logo
3:08 am - 4:00 pm
SJU
-
MDW
13h 52m
1 stop
$221Frontier
Mon, Apr 13 - Fri, Apr 17
Frontier Logo
5:30 am - 8:00 pm
MDW
-
SJU
13h 30m
1 stop
Frontier Logo
3:19 pm - 4:00 pm
SJU
-
MDW
25h 41m
1 stop
$226Frontier
Mon, Apr 13 - Fri, Apr 17
Multiple Airlines Logo
6:30 am - 11:58 pm
MDW
-
SJU
16h 28m
1 stop
Multiple Airlines Logo
11:30 am - 6:37 pm
SJU
-
MDW
32h 07m
2 stops
$228Multiple Airlines
Sat, Apr 11 - Fri, Apr 17
Frontier Logo
6:00 am - 2:01 am
MDW
-
SJU
19h 01m
1 stop
Frontier Logo
3:08 am - 4:00 pm
SJU
-
MDW
13h 52m
1 stop
$230Frontier
Thu, Apr 16 - Thu, Apr 30
Frontier Logo
9:14 am - 10:48 pm
MDW
-
SJU
12h 34m
1 stop
Frontier Logo
3:03 pm - 10:19 pm
SJU
-
MDW
8h 16m
1 stop
$231Frontier
Mon, Apr 13 - Fri, Apr 17
Multiple Airlines Logo
6:30 am - 11:58 pm
MDW
-
SJU
16h 28m
1 stop
Multiple Airlines Logo
11:02 am - 10:26 pm
SJU
-
MDW
12h 24m
1 stop
$242Multiple Airlines
Mon, Apr 20 - Thu, Apr 23
Southwest Logo
5:35 am - 1:35 pm
MDW
-
STT
7h 00m
1 stop
Southwest Logo
2:30 pm - 10:45 pm
STT
-
MDW
9h 15m
2 stops
$440Southwest
Sun, Apr 26 - Fri, May 1
Southwest Logo
5:05 am - 2:50 pm
MDW
-
PLS
8h 45m
1 stop
Southwest Logo
3:50 pm - 12:05 am
PLS
-
MDW
9h 15m
1 stop
$475Southwest
Wed, May 6 - Mon, May 11
Delta Logo
6:00 am - 1:12 pm
MDW
-
SDQ
6h 12m
1 stop
Delta Logo
2:49 pm - 9:09 pm
SDQ
-
MDW
7h 20m
1 stop
$481Delta
Mon, May 4 - Thu, May 7
Delta Logo
6:00 am - 1:12 pm
MDW
-
SDQ
6h 12m
1 stop
Delta Logo
2:49 pm - 9:09 pm
SDQ
-
MDW
7h 20m
1 stop
$482Delta
Booking Insights

KAYAK's insights & trends for Midway to Caribbean Islands flights

Get data-powered insights and trends into flights from Midway to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Chicago Midway Airport found in the last 72 hours was to Montego Bay, at $297 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $446.

What is the cheapest time of day to fly to Caribbean Islands?

The average price for all round-trip flights from Chicago Midway Airport to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally in the morning, when round-trip flights cost $534 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $534.

Can I save money by flying with a layover from Chicago Midway Airport to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $385, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Caribbean Islands is February, when tickets cost $271 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $479 and $470 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$108
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Chicago Midway Airport to Montego Bay

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Caribbean Islands?

    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 Chicago Midway Airport to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to 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 Chicago Midway Airport to Caribbean Islands?

    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 from Chicago Midway Airport to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Caribbean Islands?

    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 from Chicago Midway Airport to 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 3 airlines serving from Midway to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Caribbean Islands? 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 4344 reviews
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

4.0 Okaysangeetha, Apr 2026
AUS - SJC
Read more Southwest reviews

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Subpar. The seating on the plane is almost unbearable. We are literally touching and/or sitting on each other which is totally unacceptable and shameful. Pilots and crew was very accommodating and friendly.

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports