$116 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 11/8. 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$378
Kingston
Kingston1 stop$433
Montego Bay
Montego Bay1 stop$378
Kingston
Kingston1 stop$433

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

Wed, Nov 5 - Sun, Nov 9
Frontier Logo
2:06 pm - 3:15 pmMDW-MBJ
24h 09m1 stop
Frontier Logo
4:30 pm - 6:39 pmMBJ-MDW
27h 09m1 stop
$378Frontier
Find Deal
Fri, Oct 3 - Sun, Oct 5
Frontier Logo
5:15 pm - 12:45 pmMDW-MBJ
19h 30m1 stop
Frontier Logo
2:12 pm - 4:25 pmMBJ-MDW
26h 13m1 stop
$380Frontier
Find Deal
Tue, Oct 21 - Tue, Oct 28
Southwest Logo
7:05 am - 1:25 pmMDW-MBJ
6h 20m1 stop
Southwest Logo
12:20 pm - 8:50 pmMBJ-MDW
8h 30m1 stop
$385Southwest
Find Deal
Wed, Nov 12 - Sun, Nov 16
Frontier Logo
2:06 pm - 3:15 pmMDW-MBJ
24h 09m1 stop
Frontier Logo
4:30 pm - 6:39 pmMBJ-MDW
27h 09m1 stop
$386Frontier
Find Deal
Fri, Dec 5 - Mon, Dec 8
 Logo
3:27 pm - 12:05 pmMDW-MBJ
19h 38m2 stops
 Logo
4:53 pm - 9:32 pmMBJ-MDW
29h 39m1 stop
Sun, Nov 16 - Wed, Nov 26
Delta Logo
6:00 am - 4:34 pmMDW-MBJ
9h 34m1 stop
Delta Logo
5:59 pm - 11:32 pmMBJ-MDW
6h 33m1 stop
$391Delta
Find Deal
Tue, Dec 2 - Fri, Dec 5
Southwest Logo
6:40 am - 2:25 pmMDW-MBJ
6h 45m1 stop
Southwest Logo
1:00 pm - 9:05 pmMBJ-MDW
9h 05m1 stop
$394Southwest
Find Deal
Sun, Nov 16 - Thu, Nov 27
Delta Logo
6:48 pm - 2:11 pmMDW-MBJ
18h 23m2 stops
Delta Logo
5:59 pm - 8:52 amMBJ-MDW
15h 53m2 stops
$395Delta
Find Deal
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
Find Deal
Wed, Nov 12 - Sun, Nov 16
 Logo
2:06 pm - 3:15 pmMDW-MBJ
24h 09m1 stop
 Logo
1:12 pm - 12:02 pmMBJ-MDW
23h 50m2 stops
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 $514 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 July, when tickets cost $616 (return) on average. On the other hand, the most expensive months are October and August, when the average cost of round-trip tickets is $943 and $845 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 Saturdays.

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

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 Jamaica, 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 Jamaica, you should book around 5 weeks before departure, which saves you about 4% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$116
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 6% 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 4248 reviews
7.5Entertainment
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
Airline reviews

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!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

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.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

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.

The experience was good. No frills but I got there safe and sound and on time.

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

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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

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