$198 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 8/20. 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

Fri, Jul 25 - Fri, Aug 1
Frontier Logo
3:53 pm - 11:17 pmMBJ-MDW
7h 24m1 stop
Frontier Logo
6:40 pm - 10:49 amMDW-MBJ
16h 09m1 stop
$384Frontier
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Thu, Jul 10 - Thu, Jul 17
Frontier Logo
9:05 am - 11:17 pmMBJ-MDW
14h 12m1 stop
Frontier Logo
2:55 pm - 7:55 amMDW-MBJ
17h 00m1 stop
$385Frontier
Find Deal
Fri, Jul 18 - Thu, Jul 31
Southwest Logo
2:20 pm - 6:30 pmMBJ-MDW
4h 10mnonstop
Southwest Logo
5:00 am - 10:20 amMDW-MBJ
5h 20m1 stop
$486Southwest
Find Deal
Sat, Jun 28 - Sat, Jul 5
Southwest Logo
3:00 pm - 7:10 pmMBJ-MDW
4h 10mnonstop
Southwest Logo
5:30 am - 12:40 pmMDW-MBJ
7h 10m1 stop
$516Southwest
Find Deal
Sat, Jun 28 - Tue, Jul 8
 Logo
12:07 pm - 10:28 pmMBJ-MDW
10h 21m2 stops
 Logo
11:39 am - 7:55 amMDW-MBJ
20h 16m1 stop
Fri, Jun 27 - Tue, Jul 8
 Logo
12:07 pm - 11:18 pmMBJ-MDW
11h 11m2 stops
 Logo
11:39 am - 7:55 amMDW-MBJ
20h 16m1 stop
Tue, Jul 1 - Tue, Jul 8
Delta Logo
1:09 pm - 9:45 pmMBJ-MDW
8h 36m1 stop
Delta Logo
6:00 am - 3:34 pmMDW-MBJ
9h 34m1 stop
$646Delta
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Wed, Jun 25 - Sat, Jul 5
Delta Logo
1:09 pm - 6:41 pmMBJ-MDW
29h 32m2 stops
Delta Logo
6:00 am - 3:25 pmMDW-MBJ
9h 25m1 stop
$658Delta
Find Deal
Fri, Jul 25 - Fri, Aug 1
WestJet Logo
10:30 am - 5:10 pmMBJ-MDW
30h 40m2 stops
WestJet Logo
12:43 pm - 9:27 amMDW-MBJ
20h 44m2 stops
$1,182WestJet
Find Deal
Mon, Jun 30 - Wed, Jul 2
WestJet Logo
10:30 am - 9:45 pmMBJ-MDW
35h 15m2 stops
WestJet Logo
12:44 pm - 9:27 amMDW-MBJ
20h 43m2 stops
$1,204WestJet
Find Deal
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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 28m, and Kingston, which takes 8h 19m.

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

There are around 257 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 47% of flights departing in the morning.


Good to know

Low seasonMarch
High seasonMay
Cheapest flight$198
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 10% 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 $545. The cheapest price found on KAYAK in the last 2 weeks cost $262 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 1,798 direct flights from within Jamaica to Chicago Midway Airport. The most common day for departures is Friday, 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 $262
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

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 4287 reviews
7.6Entertainment
8.0Comfort
7.1Food
8.2Boarding
8.6Crew
Airline reviews

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.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

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.

Plz don't take away free bags and free seating

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.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Boarding was tough as we had to take a bus out to the plane and walk up a lot of stairs. Difficult with heavy carry-ons that said I got an entire empty row of seats, which was excellent for an international flight. Food was very mediocre but happy with the comfort so not complaining.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

Delta is better for short flights and very low need for customer service. Avoid for longer flights

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

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