$165 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 7/7. 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.
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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$438
Kingston
Kingston1 stop$451
Montego Bay
Montego Bay1 stop$438
Kingston
Kingston1 stop$451

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.

Recent round-trip flight deals from Midway to Jamaica

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Jamaica.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
8:55 pm - 11:53 amMDW-MBJ
14h 58m1 stop
Frontier Logo
9:13 am - 10:16 pmMBJ-MDW
13h 03m1 stop
$438Frontier
Find Deal
Fri, May 30 - Mon, Jun 2
Frontier Logo
6:35 am - 1:58 pmMDW-MBJ
7h 23m1 stop
Frontier Logo
9:35 am - 9:56 pmMBJ-MDW
12h 21m1 stop
$440Frontier
Find Deal
Mon, May 26 - Thu, May 29
Frontier Logo
6:40 am - 1:51 pmMDW-MBJ
7h 11m1 stop
Frontier Logo
9:38 am - 9:32 pmMBJ-MDW
11h 54m1 stop
$447Frontier
Find Deal
Wed, May 28 - Sun, Jun 1
Frontier Logo
4:46 pm - 7:50 amMDW-MBJ
15h 04m1 stop
Frontier Logo
9:08 am - 10:44 pmMBJ-MDW
13h 36m1 stop
$448Frontier
Find Deal
Tue, May 27 - Tue, Jun 3
Delta Logo
6:00 am - 3:30 pmMDW-MBJ
9h 30m1 stop
Delta Logo
1:02 pm - 9:28 pmMBJ-MDW
8h 26m1 stop
$449Delta
Find Deal
Sun, May 11 - Wed, May 14
Delta Logo
12:44 pm - 8:00 pmMDW-KIN
7h 16m1 stop
Delta Logo
9:00 am - 6:02 pmKIN-MDW
9h 02m1 stop
$451Delta
Find Deal
Fri, Jun 13 - Fri, Jun 20
Southwest Logo
9:00 am - 1:00 pmMDW-MBJ
4h 00mnonstop
Southwest Logo
2:20 pm - 6:30 pmMBJ-MDW
4h 10mnonstop
$462Southwest
Find Deal
Sun, Jun 8 - Tue, Jun 10
Southwest Logo
7:45 am - 2:55 pmMDW-MBJ
7h 10m1 stop
Southwest Logo
2:20 pm - 6:30 pmMBJ-MDW
4h 10mnonstop
$467Southwest
Find Deal
Sun, Jun 8 - Tue, Jun 10
 Logo
9:12 pm - 11:02 amMDW-MBJ
13h 50m2 stops
 Logo
2:02 pm - 12:55 pmMBJ-MDW
22h 53m1 stop
Fri, Jun 6 - Tue, Jun 10
 Logo
9:12 pm - 1:08 pmMDW-MBJ
15h 56m1 stop
 Logo
12:07 pm - 11:18 pmMBJ-MDW
11h 11m2 stops
Fri, Jun 13 - Mon, Jun 16
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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 $586 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 $586.

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 April, when tickets cost $644 (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 Thursday and avoid Sundays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Fridays and the most expensive ones on Saturdays.


Good to know

Low seasonNovember
High seasonAugust
Cheapest flight$165
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 11% 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 78% 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 $774.

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 4294 reviews
8.2Boarding
7.6Entertainment
8.6Crew
8.0Comfort
7.1Food
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

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

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