$108 Find Cheap Flights from Chicago Midway Airport to Jamaica

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 Jamaica departing on 5/12. 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 Midway to Jamaica

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$308
Kingston
Kingston1 stop$567
Montego Bay
Montego Bay1 stop$308
Kingston
Kingston1 stop$567

Book Cheap Midway to Jamaica 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 Jamaica 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 Jamaica

Tue, May 5 - Fri, May 8
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
$308Frontier
Tue, May 5 - Tue, May 12
Frontier Logo
3:07 pm - 12:11 pm
MDW
-
MBJ
21h 04m
2 stops
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
$310Frontier
Sun, Jul 26 - Thu, Jul 30
Southwest Logo
7:50 am - 11:45 am
MDW
-
MBJ
3h 55mnonstop
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
$318Southwest
Fri, May 8 - Tue, May 12
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 11:09 am
MBJ
-
MDW
21h 53m
1 stop
$322Frontier
Thu, May 7 - Mon, May 11
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 11:09 am
MBJ
-
MDW
21h 53m
1 stop
$324Frontier
Tue, May 12 - Tue, May 19
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
$328Frontier
Tue, May 5 - Fri, May 8
Delta Logo
12:52 pm - 8:00 pm
MDW
-
KIN
7h 08m
1 stop
Delta Logo
9:00 am - 9:26 pm
KIN
-
MDW
12h 26m
1 stop
$567Delta
Tue, May 5 - Sat, May 9
Delta Logo
10:41 am - 8:00 pm
MDW
-
KIN
9h 19m
1 stop
Delta Logo
9:00 am - 9:09 pm
KIN
-
MDW
12h 09m
1 stop
$576Delta
Tue, May 26 - Sat, May 30
Multiple Airlines Logo
10:30 am - 2:30 pm
MDW
-
KIN
28h 00m
1 stop
Multiple Airlines Logo
3:30 pm - 9:45 am
KIN
-
MDW
18h 15m
1 stop
$656Multiple Airlines
Tue, May 26 - Sat, May 30
Multiple Airlines Logo
12:27 pm - 11:07 am
MDW
-
KIN
22h 40m
2 stops
Multiple Airlines Logo
3:30 pm - 2:35 pm
KIN
-
MDW
23h 05m
1 stop
$662Multiple Airlines
Booking Insights

KAYAK's insights & trends for Midway to Jamaica flights

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

What is the cheapest Chicago Midway Airport to Jamaica flight route?

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

The cheapest ticket to Jamaica from Chicago Midway Airport found in the last 72 hours was to Montego Bay, at $307 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Montego Bay (MBJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $307.

What is the cheapest time of day to fly to Jamaica?

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

The cheapest time of day to fly to Jamaica is generally in the morning, when round-trip flights cost $612 on average. The most expensive time of day to fly to Jamaica is generally in the morning, which is peak travel time and where the average cost of a ticket is $612.

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

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 $522, prices are generally cheapest when you fly direct.

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

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 Jamaica, 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 Jamaica is October, when tickets cost $525 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $984 and $783 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Jamaica?

The average price of all round-trip flights from Chicago Midway Airport to Jamaica clicked on KAYAK for each day over the last 12 months.

When flying from Chicago Midway Airport to Jamaica, you should consider leaving on a Sunday and avoid Wednesdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Saturdays and the most expensive ones on Mondays.

Good to know

Low seasonOctober
Cheapest flight$108
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Chicago Midway Airport to Montego Bay

FAQs - booking Jamaica flights

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

    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 Jamaica.

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

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

    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 Jamaica 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 Jamaica?

    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 Jamaica up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many flights are there between Chicago Midway Airport and Jamaica per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in Jamaica, with an average flight time of 3h 50m. The most common departure time is 9:00 am and most flights take off in the morning. Each week, there are 1 flights.

Reviews of the top 3 airlines serving from Midway to Jamaica

 
Need help choosing which airline to fly with from Midway to Jamaica? 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 4328 reviews
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
8.0Comfort
Airline reviews

The new boarding process was easy and straightforward. Very pleasant.

10.0 ExcellentAnonymous, Apr 2026
LAS - OKC
Read more Southwest reviews

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

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.

Boarding was good. The flight was on time ( arrival was 20 minutes early). Inflight service was average ( US airlines have not mastered the skills of customer service yet). The food was mediocre. “ breakfast “ was downright awful and insulting. It was a piece of dough with mon descript filling that was supposed to be cheese omelette).

The tray table was broken and the food was terrible.

The gentleman at the gate I think his name is RIE was exceptional

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

They switched our terminal 3 times and we were delayed for four plus hours!!!

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.

Everything you need to know for your flight from Midway to Jamaica

Information on your arrival and departure airports