$213 Find Cheap Flights from Jamaica to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 9/20. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Cheap Flights from Jamaica to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jamaica to Midway 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 Jamaica to Midway

Thu, Oct 2 - Mon, Oct 6
Delta Logo
2:35 pm - 9:36 pmMBJ-MDW
7h 01m1 stop
Delta Logo
6:00 am - 3:34 pmMDW-MBJ
9h 34m1 stop
$339Delta
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Thu, Oct 2 - Mon, Oct 6
Southwest Logo
12:50 pm - 8:40 pmMBJ-MDW
7h 50m2 stops
Southwest Logo
5:00 am - 1:55 pmMDW-MBJ
8h 55m1 stop
$348Southwest
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Wed, Aug 13 - Wed, Oct 15
Frontier Logo
9:05 am - 1:47 pmMBJ-MDW
28h 42m1 stop
Frontier Logo
8:00 am - 7:53 amMDW-MBJ
23h 53m1 stop
$359Frontier
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Sun, Sep 14 - Sun, Sep 21
Frontier Logo
2:12 pm - 11:20 pmMBJ-MDW
9h 08m1 stop
Frontier Logo
6:20 am - 12:41 pmMDW-MBJ
6h 21m1 stop
$362Frontier
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Thu, Oct 2 - Mon, Oct 6
Southwest Logo
12:50 pm - 8:40 pmMBJ-MDW
7h 50m2 stops
Southwest Logo
8:45 pm - 2:00 pmMDW-MBJ
17h 15m2 stops
$373Southwest
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Sat, Dec 6 - Fri, Dec 12
Frontier Logo
4:53 pm - 11:05 pmMBJ-MDW
7h 12m1 stop
Frontier Logo
6:00 am - 3:33 pmMDW-MBJ
8h 33m1 stop
$383Frontier
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Wed, Aug 13 - Sun, Sep 7
Frontier Logo
9:05 am - 1:47 pmMBJ-MDW
28h 42m1 stop
Frontier Logo
6:20 am - 12:41 pmMDW-MBJ
6h 21m1 stop
$385Frontier
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Wed, Aug 20 - Sun, Aug 24
Delta Logo
2:30 pm - 9:44 pmMBJ-MDW
7h 14m1 stop
Delta Logo
6:04 am - 3:38 pmMDW-MBJ
9h 34m1 stop
$497Delta
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Sun, Sep 14 - Sun, Sep 21
WestJet Logo
12:45 pm - 1:03 pmMBJ-MDW
24h 18m2 stops
WestJet Logo
12:43 pm - 9:26 amMDW-MBJ
20h 43m2 stops
$1,242WestJet
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Wed, Aug 13 - Wed, Aug 20
WestJet Logo
12:45 pm - 1:03 pmMBJ-MDW
24h 18m2 stops
WestJet Logo
12:43 pm - 9:27 amMDW-MBJ
20h 44m2 stops
$1,621WestJet
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Booking Insights

KAYAK's insights & trends for flights to Midway

Get data-powered insights and trends for flights to Midway to help you find the cheapest flights, the best time to fly and much more.

What is a good deal for flights to Chicago Midway Airport?

If you’re looking for cheap airfare to Chicago Midway Airport, 25% of our users found tickets to Chicago Midway Airport for the following prices or less: From Montego Bay $460 round-trip.


Good to know

Low seasonSeptember
Cheapest flight$213
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Montego Bay to Chicago Midway Airport

FAQs - booking Chicago Midway Airport flights

  • How far is Chicago Midway Airport from central Chicago?

    Chicago Midway Airport is 9 miles from the center of Chicago.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $586. The cheapest price found on KAYAK in the last 2 weeks cost $236 and departed from Montego Bay Sangster Intl Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Tuesday where round-trip tickets can be as cheap as $332. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $743 on average.

  • How does KAYAK find such low prices on flights to Chicago Midway Airport?

    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 to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago Midway Airport?

    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 to Chicago Midway Airport 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 to Chicago Midway Airport?

    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 to Chicago Midway Airport 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 Chicago Midway Airport?

    The cheapest time of day to fly to Chicago Midway Airport is generally in the afternoon, when round-trip flights cost $568 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the evening, which is peak travel time and where the average cost of a ticket is $763.

  • How many direct flights to Chicago Midway Airport are there each week?

    Each week there are around 1,604 direct flights from within Jamaica to Chicago Midway Airport. The most common day for departures is Sunday, with 18% of flights taking off on this day.

Top tips for finding cheap flights to Chicago Midway Airport

  • Looking for cheap airfare to Chicago Midway Airport? 25% of our users found round-trip tickets to Chicago Midway Airport for the following prices or less: From Montego Bay $386
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

Reviews of the top airlines flying from Jamaica to Midway

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Jamaica to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Midway? 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 4241 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

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.

Check in process was terrible. Lady at counter didn’t know what she was doing

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

The crew was amazing; Von, Vera and Guadalupe were very friendly and attentive throughout the entire flight. They were friendly and welcoming to everyone. A solid and dedicated team for sure!

Terrible. I was bumped off of my original flight and spent the next six days fighting to get back on it. I lost hours of my vacation trying to get this situation corrected.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

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.

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

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