$155 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 11/16. 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

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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$371
Kingston
Kingston1 stop$506
Montego Bay
Montego Bay1 stop$371
Kingston
Kingston1 stop$506

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

Sun, Nov 2 - Thu, Nov 6
Delta Logo
5:00 am - 1:20 pmMDW-MBJ
7h 20m1 stop
Delta Logo
3:45 pm - 10:14 pmMBJ-MDW
7h 29m1 stop
$371Delta
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Sun, Nov 23 - Thu, Nov 27
Delta Logo
6:48 pm - 4:34 pmMDW-MBJ
20h 46m2 stops
Delta Logo
1:48 pm - 9:52 amMBJ-MDW
21h 04m2 stops
$376Delta
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Mon, Oct 27 - Mon, Nov 3
Delta Logo
6:00 am - 12:07 pmMDW-MBJ
6h 07m1 stop
Delta Logo
5:59 pm - 8:40 amMBJ-MDW
15h 41m2 stops
$388Delta
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Thu, Dec 11 - Sun, Dec 14
Frontier Logo
7:47 pm - 3:33 pmMDW-MBJ
18h 46m1 stop
Frontier Logo
4:53 pm - 9:52 amMBJ-MDW
17h 59m1 stop
$390Frontier
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Sat, Dec 6 - Sat, Dec 13
Frontier Logo
6:00 am - 3:33 pmMDW-MBJ
8h 33m1 stop
Frontier Logo
4:53 pm - 11:05 pmMBJ-MDW
7h 12m1 stop
$399Frontier
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Sun, Oct 26 - Tue, Nov 4
Southwest Logo
6:25 am - 11:55 amMDW-MBJ
5h 30m1 stop
Southwest Logo
1:00 pm - 9:05 pmMBJ-MDW
9h 05m1 stop
$404Southwest
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Sun, Nov 9 - Fri, Nov 14
Multiple Airlines Logo
6:15 am - 3:15 pmMDW-MBJ
8h 00m1 stop
Multiple Airlines Logo
4:30 pm - 12:37 pmMBJ-MDW
21h 07m2 stops
$406Multiple Airlines
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Sat, Nov 15 - Wed, Nov 19
Southwest Logo
6:40 am - 2:05 pmMDW-MBJ
6h 25m1 stop
Southwest Logo
1:00 pm - 9:05 pmMBJ-MDW
9h 05m1 stop
$428Southwest
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Fri, Nov 14 - Thu, Nov 20
Multiple Airlines Logo
1:37 pm - 12:02 pmMDW-MBJ
21h 25m2 stops
Multiple Airlines Logo
2:43 pm - 10:43 pmMBJ-MDW
9h 00m1 stop
$440Multiple Airlines
Find Deal
Tue, Nov 11 - Tue, Nov 18
WestJet Logo
1:47 pm - 3:33 pmMDW-KIN
24h 46m2 stops
WestJet Logo
4:30 pm - 1:07 pmKIN-MDW
21h 37m3 stops
$753WestJet
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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 $1,954 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 $1,954.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $508 on average.

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 $549 (return) on average. On the other hand, the most expensive months are August and June, when the average cost of round-trip tickets is $843 and $763 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 Friday 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 Thursdays and the most expensive ones on Mondays.

Good to know

Low seasonOctober
Cheapest flight$155
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 12% increase in price.
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.

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

    The cheapest time of day to fly to Jamaica is generally in the evening, when round-trip flights cost $436 on average. Morning departures are around 66% more expensive than evening flights, 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 $725.

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 4235 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

4.0 OkayAnnette, Oct 2025LGA - MCI
Read more Southwest reviews

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

The flight was an hour and a half late departing which was inconvenient

Delay in SLC jammed us up in Chicago. Got caught up in rush hour traffic

The crew took good care of us. The flight from ATL to SFO is a longer one, and there were multiple beverage offerings. I like the 757's that Delta uses. Good airplane that is comfortable. I do wish Delta would separate Priority boarding from the better seats. I would gladly take a smaller seat in an open row than be jammed into Comfort just to get priority boarding, just to make sure I don't have to check a bag.

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Gate agent rushed to fill hot jetway with crowd so it took over 12 minutes to go from gate to plane. Just like a discount airline Pooly prepared cabin and third time that claim of rough air prevented any cabin service. Friends on a Southwest flight at similar time had service.

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

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.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

I think Frontier was very good at communication. Their app worked very well. Loading was great and the flight was nice and easy.

This airline sucks. They offer low rates then charge you for everything, the app does not work well, the seats are the most uncomfortable. Maintenance issues on the flight, and you still have to sit through their credit card commercials. People are nice enough but does not make up for overall poor experience.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

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

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