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$325 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 6/22. 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
0 bags
Sat 6/29
Sat 7/6

Search 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
In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Flights to Midway - Travel Insights & Trends

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 the cheapest day to fly to Chicago?

The average price of all flights to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where tickets can be as cheap as $424. On the other hand, the most expensive day to fly is Tuesday, where prices are $743 on average.

What is the cheapest time of day to fly to Chicago Midway Airport?

The average price for all flights to Chicago Midway Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago Midway Airport is generally in the afternoon, when flights cost $424 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the morning, which is peak travel time and where the average cost of a ticket is $429.

Which airline offers the most flights to Chicago Midway Airport?

Of the 5 airlines that fly to Chicago Midway Airport, Southwest offers the most flights, with around 1,630 per week, followed by Frontier with 88 flights per week.

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 24m, and Kingston, which takes 8h 27m.

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

There are around 259 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 41% of flights departing in the morning.

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

Each week there are around 1,808 direct flights from within Jamaica to Chicago Midway Airport. The most common day for departures is Monday, with 15% of flights taking off on this day.

How many long-haul flights are there to Chicago Midway Airport each week?

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago Midway Airport. Instead, there are 7 medium-haul flights (3-6 hour flight duration), with the most arriving from Montego Bay.

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 7 direct flights each week.

Good to know

Low season

May

High season

May

Cheapest flight

$325
Best time to beat the crowds with an average 54% drop in price.
Most popular time to fly and prices are also 54% 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 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.

See more FAQs

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.

Prefer to fly non-stop to Chicago Midway?

Find which airlines fly direct to Midway, which days they fly and book direct flights.

Nonstop departures

Jamaica to Chicago Midway

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

See more direct flights

Nonstop returns

Chicago Midway to Jamaica

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

See more direct flights
See more direct flights

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.
6.2
FrontierOverall score based on 4016 reviews
5.8Comfort
7.1Crew
5.1Food
4.9Entertainment
6.6Boarding
Airline reviews

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

2.0 MediocreTeddy, May 2024LAS - SAN
Read more about Frontier reviews

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Book cheap flights from Jamaica to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
6/22Sat
2 stops
28h 19mMBJ-MDW
$325
6/22Sat
1 stopFrontier
24h 16mMBJ-MDW
$328
6/10Mon
1 stopFrontier
25h 58mMBJ-MDW
$391
6/10Mon
2 stops
41h 42mMBJ-MDW
$419
6/30Sun
2 stops
34h 53mMBJ-MDW
$420
6/30Sun
1 stopFrontier
23h 10mMBJ-MDW
$435
6/24Mon
2 stops
29h 12mMBJ-MDW
$453
6/9Sun
1 stopDelta
7h 16mMBJ-MDW
$792
6/24Mon
2 stopsDelta
18h 18mMBJ-MDW
$798
6/9Sun
2 stopsDelta
18h 18mMBJ-MDW
$1,570

Search by stops

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Last minute flights to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
6/4Tue
multi-stopDelta
16h 07mMBJ-MDW
6/11Tue
multi-stopDelta
17h 14mMDW-MBJ
$1,920

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Flights to Chicago Midway Airport

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Jamaica

Cabin classes: