$158 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 7/12. 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

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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$376
Kingston
Kingston2 stops$575
Montego Bay
Montego Bay1 stop$376
Kingston
Kingston2 stops$575

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, Jul 8 - Fri, Jul 11
Frontier Logo
11:39 am - 2:45 pmMDW-MBJ
27h 06m1 stop
Frontier Logo
9:05 am - 11:17 pmMBJ-MDW
14h 12m1 stop
$376Frontier
Find Deal
Sat, Jul 12 - Wed, Jul 23
Frontier Logo
6:20 am - 2:40 pmMDW-MBJ
8h 20m1 stop
Frontier Logo
3:53 pm - 1:47 pmMBJ-MDW
21h 54m1 stop
$382Frontier
Find Deal
Mon, Aug 25 - Fri, Aug 29
Delta Logo
6:00 am - 11:55 amMDW-MBJ
5h 55m1 stop
Delta Logo
2:30 pm - 9:49 pmMBJ-MDW
7h 19m1 stop
$385Delta
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Thu, Sep 11 - Mon, Sep 15
Frontier Logo
7:23 pm - 7:53 amMDW-MBJ
12h 30m1 stop
Frontier Logo
9:13 am - 6:18 pmMBJ-MDW
9h 05m1 stop
$387Frontier
Find Deal
Sat, Jul 12 - Thu, Jul 24
Frontier Logo
6:20 am - 7:55 amMDW-MBJ
25h 35m1 stop
Frontier Logo
9:10 am - 11:17 pmMBJ-MDW
14h 07m1 stop
$388Frontier
Find Deal
Fri, Aug 15 - Wed, Aug 20
Delta Logo
6:04 am - 3:38 pmMDW-MBJ
9h 34m1 stop
Delta Logo
2:30 pm - 9:49 pmMBJ-MDW
7h 19m1 stop
$410Delta
Find Deal
Tue, Jul 8 - Thu, Jul 10
Southwest Logo
9:00 am - 1:00 pmMDW-MBJ
4h 00mnonstop
Southwest Logo
2:55 pm - 11:40 pmMBJ-MDW
8h 45m1 stop
$420Southwest
Find Deal
Tue, Jul 8 - Thu, Jul 10
Southwest Logo
9:00 am - 1:00 pmMDW-MBJ
4h 00mnonstop
Southwest Logo
2:20 pm - 6:30 pmMBJ-MDW
4h 10mnonstop
$423Southwest
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Thu, Aug 21 - Mon, Aug 25
 Logo
2:05 pm - 11:09 amMDW-MBJ
21h 04m2 stops
 Logo
10:03 am - 5:16 pmMBJ-MDW
7h 13m1 stop
Sat, Jun 28 - Mon, Aug 18
 Logo
9:12 pm - 11:02 amMDW-MBJ
13h 50m2 stops
 Logo
10:03 am - 5:36 pmMBJ-MDW
7h 33m1 stop
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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 $501 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 $501.

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 $606, 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 July, when tickets cost $620 (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.

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 8 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$158
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 69% 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 $736.

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 4278 reviews
7.6Entertainment
8.0Comfort
7.1Food
8.2Boarding
8.6Crew
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

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.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Overall, aside from the baggage issue, it was as good as one expects.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

I want to single out flight attendant Mitch who was in the Premium Economy section. When my wife’s hearing aide dropped through the cushion under the seat he was able to locate it and return it to her. Food was a different matter. Dinner was fine. Breakfast was another matter. They had a yogurt dish that the ran out of and the alternative was not very good according to those we talked to.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Flight was delayed long enough that I was misding my connecting flight. The agents could not get me on a comparable flight, nor could they get me s Main Cabin seat I had paid for, nor could they get me on a comparable connecting flight. The gate agent would not issue meal vouchers, even though I was delayed over six hours! I had to spend over an hour and 15 minutes with customer service on the phone to See if they could get me on a better flight and get a meal voucher. Customer service was not helpful enough in trying to find alternate flights and it Ended up taking me 24 hours for a 12 hour trip!! Delta does not provide upgrades NOR will they even give you a pass for a few hours to their lounge. They claim that they do not issue daily passes to their lounge anymore. I call BS since this would be no extra cost to them to provide excellent customer service and give you a few hours to relax in comfort when you’re sitting in a crowded airport and your flight has been screwed up for that many hours.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

I liked the price of the flight and the chance to buy a seat with no person seated in the middle seat.. Also the flight was right on time.

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

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