$118 Find Cheap Flights from Chicago Midway Airport to Caribbean Islands - Compare and Save

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 7/28. 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 Cana1 stop$429
Santo Domingo
Santo Domingo1 stop$388
Montego Bay
Montego Bay1 stop$452
Oranjestad
Oranjestad1 stop$638
Nassau
Nassau1 stop$392
Kingston
Kingston1 stop$464
Simpson Bay
Simpson Bay1 stop$325
Providenciales
Providenciales1 stop$473
George Town
George Town2 stops$464
St. John's
St. John's1 stop$755
Punta Cana
Punta Cana1 stop$429
Santo Domingo
Santo Domingo1 stop$388
Montego Bay
Montego Bay1 stop$452
Oranjestad
Oranjestad1 stop$638
Nassau
Nassau1 stop$392
Kingston
Kingston1 stop$464
Simpson Bay
Simpson Bay1 stop$325
Providenciales
Providenciales1 stop$473
George Town
George Town2 stops$464
St. John's
St. John's1 stop$755

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

Sat, Aug 22 - Sun, Aug 30
Southwest Logo
7:05 am - 6:15 pm
MDW
-
SJU
10h 10m
1 stop
Southwest Logo
9:25 pm - 8:45 am
SJU
-
MDW
12h 20m
1 stop
$266Southwest
Fri, Aug 28 - Fri, Sep 4
Delta Logo
12:46 pm - 10:29 pm
MDW
-
SJU
8h 43m
1 stop
Delta Logo
12:56 pm - 10:36 pm
SJU
-
MDW
10h 40m
1 stop
$276Delta
Sat, Aug 15 - Wed, Aug 19
Delta Logo
6:05 am - 4:38 pm
MDW
-
SJU
9h 33m
1 stop
Delta Logo
12:56 pm - 10:36 pm
SJU
-
MDW
10h 40m
1 stop
$281Delta
Fri, Aug 21 - Tue, Aug 25
Southwest Logo
1:00 pm - 10:50 pm
MDW
-
SJU
8h 50m
2 stops
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
$286Southwest
Thu, Sep 24 - Mon, Sep 28
Southwest Logo
9:20 am - 8:05 pm
MDW
-
SJU
9h 45m
2 stops
Southwest Logo
5:00 am - 12:25 pm
SJU
-
MDW
8h 25m
2 stops
$291Southwest
Sat, Aug 15 - Sun, Aug 23
Southwest Logo
7:50 am - 6:05 pm
MDW
-
SJU
9h 15m
2 stops
Southwest Logo
9:25 pm - 8:45 am
SJU
-
MDW
12h 20m
1 stop
$296Southwest
Fri, Aug 14 - Wed, Aug 19
Southwest Logo
1:00 pm - 10:50 pm
MDW
-
SJU
8h 50m
2 stops
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
$301Southwest
Sat, Sep 19 - Sat, Sep 26
Frontier Logo
7:25 am - 1:31 pm
MDW
-
MBJ
6h 06m
1 stop
Frontier Logo
2:49 pm - 9:58 pm
MBJ
-
MDW
7h 09m
1 stop
$452Frontier
Tue, Jul 28 - Tue, Aug 4
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
Frontier Logo
3:31 pm - 9:51 am
PUJ
-
MDW
19h 20m
1 stop
$458Frontier
Sat, Aug 15 - Sat, Aug 22
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
Frontier Logo
3:37 pm - 10:55 am
PUJ
-
MDW
20h 18m
1 stop
$471Frontier
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 5 days was to Montego Bay, at $467 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 5 days was $578.

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 $658 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 $658.

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 $420, 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 May, when tickets cost $172 (return) on average. On the other hand, the most expensive months are October and June, when the average cost of round-trip tickets is $468 and $467 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 3 weeks before departure, which saves you about 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$118
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 30% increase in price.
Flight from Chicago Midway Airport to Simpson 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.
7.9
SouthwestOverall score based on 4244 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent experience. WiFi worked on this leg of My trip

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

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.

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

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

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 !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports