$184 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 10/23. 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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Flight Deals

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

tir., nov. 25 - man., dec. 1
Southwest Logo
3:25 pm - 11:50 pmMBJ-MDW
9h 25m2 stops
Southwest Logo
5:20 am - 12:50 pmMDW-MBJ
6h 30m1 stop
$394Southwest
Find Deal
tir., nov. 25 - man., dec. 1
Southwest Logo
3:25 pm - 11:50 pmMBJ-MDW
9h 25m2 stops
Southwest Logo
9:40 pm - 2:55 pmMDW-MBJ
16h 15m2 stops
$424Southwest
Find Deal
tor., dec. 25 - man., dec. 29
Delta Logo
8:00 am - 5:20 pmMBJ-MDW
10h 20m2 stops
Delta Logo
12:43 pm - 8:36 pmMDW-MBJ
6h 53m1 stop
$506Delta
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man., sep. 29 - man., okt. 6
Frontier Logo
2:12 pm - 11:20 pmMBJ-MDW
9h 08m1 stop
Frontier Logo
6:20 am - 12:45 pmMDW-MBJ
6h 25m1 stop
$548Frontier
Find Deal
søn., sep. 28 - søn., okt. 5
Frontier Logo
2:12 pm - 11:20 pmMBJ-MDW
9h 08m1 stop
Frontier Logo
6:20 am - 12:41 pmMDW-MBJ
6h 21m1 stop
$596Frontier
Find Deal
tor., dec. 25 - man., dec. 29
Southwest Logo
1:50 pm - 10:35 pmMBJ-MDW
9h 45m2 stops
Southwest Logo
9:40 pm - 2:55 pmMDW-MBJ
16h 15m2 stops
$604Southwest
Find Deal
søn., sep. 28 - søn., okt. 5
Frontier Logo
2:12 pm - 7:11 amMBJ-MDW
16h 59m2 stops
Frontier Logo
6:20 am - 12:41 pmMDW-MBJ
6h 21m1 stop
$618Frontier
Find Deal
man., sep. 29 - man., okt. 6
Multiple Airlines Logo
10:52 am - 6:43 pmMBJ-MDW
7h 51m1 stop
Multiple Airlines Logo
9:47 pm - 11:00 amMDW-MBJ
13h 13m2 stops
$683Multiple Airlines
Find Deal

Everything you should know

Cheapest round-trip
$394
Southwest
tir. 11/25man. 12/1
MBJ - MDW • 2 stops
Cheapest one-way
$184
Frontier
tor. 10/23
MBJ - MDW • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
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.

How long is the flight to Chicago Midway Airport?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Montego Bay, which takes 4h 25m, and Kingston, which takes 10h 38m.

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

There are around 417 direct flights from within Jamaica to Chicago Midway Airport every day. Most flights depart in the morning, with 6:00 am the most common departure time and 53% of flights departing in the morning.

Good to know

Low seasonSeptember
Cheapest flight$184
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 4% 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.

  • 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 2,914 direct flights from within Jamaica to Chicago Midway Airport. The most common day for departures is Monday, with 16% of flights taking off on this day.

Top tips for finding cheap flights to Chicago Midway Airport

  • 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 airline 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 4242 reviews
8.6Crew
7.0Food
7.5Entertainment
8.0Comfort
8.1Boarding
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.

Was good. I miss the free 2 checked bags. That was part of what made Southwest special

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.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Valparaiso
Lansing
Munster
Chesterton
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

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