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MDW - KIN

$267 Find cheap flights from Chicago Midway Airport to Kingston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Kingston departing on 6/6. 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
Wed 6/5
Wed 6/12

Search hundreds of travel sites at once for deals on flights to Kingston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kingston, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kingston, as well as popular online travel agencies
In the last 7 days travelers have searched 42,830,901 times on KAYAK, and here is why:

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Cheap flight deals from Midway to Kingston (MDW-KIN)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Kingston 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 and deals for you by selecting your travel dates.
Choose your dates
1:05 pm - 7:47 pmMDW-KIN
6h 42m1 stop
9:00 am - 9:44 pmKIN-MDW
12h 44m1 stop
$480Delta
Find Deal
Wed, Sep 18 - Thu, Sep 26
5:59 pm - 7:47 pmMDW-KIN
25h 48m2 stops
9:00 am - 8:45 amKIN-MDW
23h 45m2 stops
$485Delta
Find Deal
Mon, Sep 23 - Tue, Oct 1
3:45 pm - 7:47 pmMDW-KIN
28h 02m1 stop
9:00 am - 9:44 pmKIN-MDW
12h 44m1 stop
$488Delta
Find Deal
Mon, Sep 23 - Thu, Sep 26
6:50 pm - 7:47 pmMDW-KIN
24h 57m1 stop
9:00 am - 8:45 amKIN-MDW
23h 45m2 stops
$493Delta
Find Deal
Mon, Sep 23 - Tue, Oct 1
9:35 am - 7:47 pmMDW-KIN
34h 12m2 stops
9:00 am - 5:59 pmKIN-MDW
8h 59m1 stop
$498Delta
Find Deal
Sat, Sep 21 - Fri, Sep 27
1:10 pm - 7:47 pmMDW-KIN
30h 37m2 stops
9:00 am - 12:31 pmKIN-MDW
27h 31m2 stops
$504Delta
Find Deal
Wed, Sep 18 - Sat, Sep 28
6:00 am - 7:56 pmMDW-KIN
13h 56m1 stop
9:00 am - 10:01 pmKIN-MDW
13h 01m1 stop
$510Delta
Find Deal
Sat, May 25 - Wed, May 29
10:11 am - 7:47 pmMDW-KIN
9h 36m1 stop
9:00 am - 5:16 pmKIN-MDW
8h 16m1 stop
$540Delta
Find Deal
Sat, Sep 21 - Sat, Sep 28
2:14 pm - 11:18 amMDW-KIN
21h 04m3 stops
7:00 pm - 10:07 amKIN-MDW
15h 07m1 stop
Fri, Jun 14 - Mon, Jun 17
3:45 pm - 1:14 pmMDW-KIN
21h 29m2 stops
2:05 pm - 11:02 amKIN-MDW
20h 57m2 stops
$3,110WestJet
Find Deal
Fri, May 17 - Fri, May 24

Flights from Midway to Kingston - Travel Insights & Trends

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

What is the cheapest month to fly from Chicago Midway Airport to Kingston?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Kingston, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Kingston is January, where tickets cost $477 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is $1,113 and $638 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Kingston?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Kingston, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Kingston, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 20 days before departure.

Good to know

Cheapest flight

$267
Flight from Chicago Midway Airport to Kingston

When to book flights from Midway to Kingston

Are your dates flexible? Find out the best times to travel from Midway to Kingston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Kingston flights

  • What is the cheapest flight from Chicago Midway Airport to Kingston?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Kingston was $267 for a one-way ticket and $480 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Kingston?

    Yes, you’ll need a passport to travel to Kingston from Chicago Midway Airport.

  • Which airports will I be using when flying from Chicago Midway Airport to Kingston?

    Chicago Midway Airport airport is called Chicago Midway and the only airport in Kingston is Kingston Norman Manley.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Kingston?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Kingston?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Kingston.

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

    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 from Chicago Midway Airport to Kingston.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kingston from 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 from Chicago Midway Airport to Kingston?

    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 Kingston with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and KIN can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Kingston?

    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 Kingston from 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 airline flying from Midway to Kingston

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Kingston. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Kingston? 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
DeltaOverall score based on 10826 reviews
8.6Crew
7.9Comfort
7.4Food
8.2Boarding
8.0Entertainment
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

Book cheap flights from Chicago to Kingston

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Kingston found on KAYAK in the last 72 hours.
6/6Thu
2 stopsDelta
10h 24mMDW-KIN
$267
6/6Thu
2 stopsDelta
10h 24mMDW-KIN
$414
7/20Sat
2 stopsDelta
10h 27mMDW-KIN
$522

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Last minute flights from Midway to Kingston

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 from Chicago to Kingston that are departing in the next 10 days.
5/8Wed
multi-stop
28h 25mMDW-KIN
5/10Fri
multi-stop
24h 02mKIN-MDW
$869
5/8Wed
multi-stop
10h 00mMDW-KIN
5/10Fri
multi-stop
16h 32mKIN-MDW
$958
5/8Wed
multi-stop
10h 00mMDW-KIN
5/10Fri
multi-stop
26h 52mKIN-MDW
$1,099

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Chicago Midway Airport - Kingston Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Kingston (KIN)Jamaica

Cabin classes:

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