$153 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 2/12. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$351
Delta
Thu 5/14Mon 5/18
MBJ - MDW • 1 stop
Cheapest non-stop
$501
Southwest
Sun 3/15Sun 3/22
MBJ - MDW • Non-stop
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We hope you love your trip to Midway!
Flight Deals
Booking Insights
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

Thu, May 14 - Mon, May 18
Delta Logo
2:40 pm - 9:45 pm
MBJ
-
MDW
7h 05m
1 stop
Delta Logo
6:00 am - 1:16 pm
MDW
-
MBJ
7h 16m
1 stop
$351Delta
Sun, Mar 15 - Sun, Mar 22
Southwest Logo
3:55 pm - 12:50 am
MBJ
-
MDW
8h 55m
1 stop
Southwest Logo
11:10 am - 2:55 pm
MDW
-
MBJ
3h 45mnonstop
$459Southwest
Sun, Mar 15 - Sun, Mar 22
Southwest Logo
12:30 pm - 4:50 pm
MBJ
-
MDW
4h 20mnonstop
Southwest Logo
11:10 am - 2:55 pm
MDW
-
MBJ
3h 45mnonstop
$501Southwest
Sat, Mar 14 - Sat, Mar 21
Southwest Logo
2:20 pm - 6:35 pm
MBJ
-
MDW
4h 15mnonstop
Southwest Logo
8:45 am - 12:35 pm
MDW
-
MBJ
3h 50mnonstop
$531Southwest
Sun, Mar 1 - Tue, Mar 3
Southwest Logo
3:10 pm - 10:45 pm
MBJ
-
MDW
8h 35m
1 stop
Southwest Logo
6:50 am - 2:10 pm
MDW
-
MBJ
6h 20m
1 stop
$586Southwest
Sun, Mar 1 - Tue, Mar 3
Southwest Logo
1:30 pm - 12:55 am
MBJ
-
MDW
12h 25m
2 stops
Southwest Logo
6:50 am - 2:10 pm
MDW
-
MBJ
6h 20m
1 stop
$641Southwest
Sun, Mar 15 - Sun, Mar 22
Southwest Logo
12:45 pm - 12:10 am
MBJ
-
MDW
11h 25m
2 stops
Southwest Logo
11:10 am - 2:55 pm
MDW
-
MBJ
3h 45mnonstop
$689Southwest
Sat, Mar 14 - Sat, Mar 21
Southwest Logo
12:00 pm - 8:10 pm
MBJ
-
MDW
8h 10m
1 stop
Southwest Logo
8:45 am - 12:35 pm
MDW
-
MBJ
3h 50mnonstop
$728Southwest
Sat, Mar 14 - Sat, Mar 21
Multiple Airlines Logo
6:25 pm - 3:20 pm
MBJ
-
MDW
20h 55m
2 stops
Multiple Airlines Logo
12:45 pm - 5:05 pm
MDW
-
MBJ
28h 20m
2 stops
$814Multiple Airlines
Sat, Mar 14 - Sat, Mar 21
Southwest Logo
2:05 pm - 12:50 am
MBJ
-
MDW
10h 45m
2 stops
Southwest Logo
6:30 am - 1:55 pm
MDW
-
MBJ
7h 25m
1 stop
$862Southwest
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 23m, and Kingston, which takes 9h 17m.

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

There are around 237 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 50% of flights departing in the morning.

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Good to know

Cheapest flight$153
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 many cities have direct flights to Chicago Midway Airport?

    From Jamaica, there are direct flights to Chicago Midway Airport from 1 city. This city is Montego Bay and there are 1 direct flights each week.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Saturday where tickets can be as cheap as $531. On the other hand, the most expensive day to fly is Monday, where prices are $689 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 flights cost $543 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 1,658 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

  • 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 4267 reviews
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Traveling to a place near Midway?

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

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

Chicago Midway Airport (MDW)