$138 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 12/6. 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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Best Jamaica Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$370
Kingston
Kingston1 stop$381
Montego Bay
Montego Bay1 stop$370
Kingston
Kingston1 stop$381

Cheap Flights from Midway to Jamaica

 
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, Aug 5 - Sat, Aug 23
Frontier Logo
11:39 am - 2:40 pmMDW-MBJ
27h 01m1 stop
Frontier Logo
9:58 am - 11:08 pmMBJ-MDW
13h 10m1 stop
$370Frontier
Find Deal
Sat, Sep 13 - Sat, Sep 20
Frontier Logo
6:10 am - 12:45 pmMDW-MBJ
6h 35m1 stop
Frontier Logo
2:05 pm - 10:33 pmMBJ-MDW
8h 28m1 stop
$374Frontier
Find Deal
Wed, Sep 24 - Tue, Sep 30
Delta Logo
10:35 am - 8:00 pmMDW-KIN
9h 25m1 stop
Delta Logo
9:00 am - 9:36 pmKIN-MDW
12h 36m1 stop
$381Delta
Find Deal
Sun, Sep 7 - Sat, Sep 13
Frontier Logo
6:20 am - 12:45 pmMDW-MBJ
6h 25m1 stop
Frontier Logo
2:05 pm - 10:33 pmMBJ-MDW
8h 28m1 stop
$384Frontier
Find Deal
Mon, Aug 25 - Fri, Aug 29
Delta Logo
6:00 am - 3:36 pmMDW-MBJ
9h 36m1 stop
Delta Logo
2:30 pm - 9:44 pmMBJ-MDW
7h 14m1 stop
$385Delta
Find Deal
Wed, Sep 24 - Tue, Sep 30
Delta Logo
9:35 am - 8:00 pmMDW-KIN
10h 25m2 stops
Delta Logo
9:00 am - 5:35 pmKIN-MDW
8h 35m1 stop
$386Delta
Find Deal
Wed, Oct 15 - Sat, Oct 18
Frontier Logo
8:00 am - 7:53 amMDW-MBJ
23h 53m1 stop
Frontier Logo
9:13 am - 11:09 pmMBJ-MDW
13h 56m1 stop
$389Frontier
Find Deal
Fri, Aug 22 - Mon, Aug 25
Frontier Logo
10:58 am - 8:48 amMDW-MBJ
21h 50m1 stop
Frontier Logo
9:05 am - 9:02 amMBJ-MDW
23h 57m1 stop
$390Frontier
Find Deal
Sun, Aug 24 - Mon, Sep 8
Delta Logo
6:04 am - 8:25 pmMDW-KIN
14h 21m1 stop
Delta Logo
9:25 am - 9:26 pmKIN-MDW
12h 01m1 stop
$391Delta
Find Deal
Mon, Aug 4 - Thu, Aug 21
 Logo
1:11 pm - 11:05 amMDW-MBJ
21h 54m3 stops
 Logo
10:22 am - 8:42 amMBJ-MDW
22h 20m2 stops
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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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Jamaica.

The cheapest ticket to Jamaica from Chicago Midway Airport found in the last 72 hours was to Montego Bay, at $455 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 $455.

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 $558, 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 November, when tickets cost $625 (return) on average. On the other hand, the most expensive months are December and October, when the average cost of round-trip tickets is $1,001 and $943 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. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.


Good to know

Low seasonJanuary
High seasonJune
Cheapest flight$138
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 2% 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 67% 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 $726.

Reviews of the top airlines flying 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 4243 reviews
7.0Food
7.6Entertainment
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

4.0 OkayGreg, Jul 2025PDX - DEN
Read more Southwest reviews

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

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

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

this crew didn't care much. bumping carts into seats more times than i care to remember

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

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

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