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Cheap flights from Chicago Midway Airport to Kingston from $178

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Kingston departing on 10/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Kingston

Cheap round-trip flights

Delta Logo
6:00 am - 8:00 pmMDW-KIN
14h 00m1 stop
Delta Logo
9:00 am - 10:14 pmKIN-MDW
13h 14m1 stop
$433Delta
Find Deal
Mon, Oct 13 - Sat, Oct 18
Delta Logo
6:00 am - 8:00 pmMDW-KIN
14h 00m1 stop
Delta Logo
9:00 am - 6:25 pmKIN-MDW
9h 25m2 stops
$438Delta
Find Deal
Mon, Oct 13 - Sat, Oct 18
Delta Logo
10:35 am - 8:00 pmMDW-KIN
8h 25m1 stop
Delta Logo
9:00 am - 9:46 pmKIN-MDW
13h 46m1 stop
$445Delta
Find Deal
Mon, Feb 2 - Mon, Feb 9
Delta Logo
9:30 am - 8:00 pmMDW-KIN
9h 30m2 stops
Delta Logo
9:00 am - 6:34 pmKIN-MDW
10h 34m2 stops
$449Delta
Find Deal
Sat, Feb 28 - Tue, Mar 3
Delta Logo
12:43 pm - 8:00 pmMDW-KIN
7h 17m1 stop
Delta Logo
9:00 am - 9:36 pmKIN-MDW
12h 36m1 stop
$483Delta
Find Deal
Mon, Sep 29 - Thu, Oct 2
Delta Logo
6:00 am - 8:00 pmMDW-KIN
14h 00m1 stop
Delta Logo
9:00 am - 6:35 pmKIN-MDW
9h 35m2 stops
$488Delta
Find Deal
Mon, Sep 29 - Thu, Oct 2
Multiple Airlines Logo
8:05 am - 8:05 pmMDW-KIN
12h 00m2 stops
Multiple Airlines Logo
6:25 pm - 4:24 pmKIN-MDW
21h 59m1 stop
$563Multiple Airlines
Find Deal
Wed, Oct 8 - Mon, Oct 13
WestJet Logo
10:47 am - 3:33 pmMDW-KIN
27h 46m2 stops
WestJet Logo
4:30 pm - 6:18 pmKIN-MDW
26h 48m2 stops
$3,263WestJet
Find Deal
Tue, Nov 18 - Tue, Dec 2
WestJet Logo
10:35 am - 3:30 pmMDW-KIN
27h 55m2 stops
WestJet Logo
4:30 pm - 1:08 pmKIN-MDW
21h 38m2 stops
$3,375WestJet
Find Deal
Mon, Feb 2 - Mon, Feb 9
WestJet Logo
10:35 am - 3:30 pmMDW-KIN
51h 55m2 stops
WestJet Logo
4:30 pm - 1:08 pmKIN-MDW
21h 38m2 stops
$3,410WestJet
Find Deal
Sat, Feb 7 - Tue, Feb 10

Delta flights from Chicago Midway Airport to Kingston

Our best Delta deals on Chicago Midway Airport to Kingston flight tickets
Delta
Oct 13
MDW6:00 amChicago Midway
14h 00m
1 stop
KIN8:00 pmKingston Norman Manley
Oct 18
KIN9:00 amKingston Norman Manley
13h 14m
1 stop
MDW10:14 pmChicago Midway
$433
Find similar
Delta
Oct 13
MDW6:00 amChicago Midway
14h 00m
1 stop
KIN8:00 pmKingston Norman Manley
Oct 18
KIN9:00 amKingston Norman Manley
9h 25m
2 stops
MDW6:25 pmChicago Midway
$438
Find similar
Delta
Feb 2
MDW10:35 amChicago Midway
8h 25m
1 stop
KIN8:00 pmKingston Norman Manley
Feb 9
KIN9:00 amKingston Norman Manley
13h 46m
1 stop
MDW9:46 pmChicago Midway
$445
Find similar

WestJet flights from Chicago Midway Airport to Kingston

Our best WestJet deals on Chicago Midway Airport to Kingston flight tickets
WestJet
Nov 18
MDW10:47 amChicago Midway
27h 46m
2 stops
KIN3:33 pmKingston Norman Manley
Dec 2
KIN4:30 pmKingston Norman Manley
26h 48m
2 stops
MDW6:18 pmChicago Midway
$3,263
Find similar
WestJet
Feb 2
MDW10:35 amChicago Midway
27h 55m
2 stops
KIN3:30 pmKingston Norman Manley
Feb 9
KIN4:30 pmKingston Norman Manley
21h 38m
2 stops
MDW1:08 pmChicago Midway
$3,375
Find similar
WestJet
Feb 7
MDW10:35 amChicago Midway
51h 55m
2 stops
KIN3:30 pmKingston Norman Manley
Feb 10
KIN4:30 pmKingston Norman Manley
21h 38m
2 stops
MDW1:08 pmChicago Midway
$3,410
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Kingston that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Kingston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 10/13

6:00 am-8:00 pm

1 stop14h 00m

Kingston Norman Manley

Sat 10/18

9:00 am-10:14 pm

1 stop13h 14m

$433

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 10/13

6:00 am-8:00 pm

1 stop14h 00m

Kingston Norman Manley

Sat 10/18

9:00 am-6:25 pm

2 stops9h 25m

$438

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 2/2

10:35 am-8:00 pm

1 stop8h 25m

Kingston Norman Manley

Mon 2/9

9:00 am-9:46 pm

1 stop13h 46m

$445

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 2/28

9:30 am-8:00 pm

2 stops9h 30m

Kingston Norman Manley

Tue 3/3

9:00 am-6:34 pm

2 stops10h 34m

$449

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 9/29

12:43 pm-8:00 pm

1 stop7h 17m

Kingston Norman Manley

Thu 10/2

9:00 am-9:36 pm

1 stop12h 36m

$483

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 9/29

6:00 am-8:00 pm

1 stop14h 00m

Kingston Norman Manley

Thu 10/2

9:00 am-6:35 pm

2 stops9h 35m

$488

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 10/8

8:05 am-8:05 pm

2 stops12h 00m

Kingston Norman Manley

Mon 10/13

6:25 pm-4:24 pm

1 stop21h 59m

$563

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 11/18

10:47 am-3:33 pm

2 stops27h 46m

Kingston Norman Manley

Tue 12/2

4:30 pm-6:18 pm

2 stops26h 48m

$3,263

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 2/2

10:35 am-3:30 pm

2 stops27h 55m

Kingston Norman Manley

Mon 2/9

4:30 pm-1:08 pm

2 stops21h 38m

$3,375

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 2/7

10:35 am-3:30 pm

2 stops51h 55m

Kingston Norman Manley

Tue 2/10

4:30 pm-1:08 pm

2 stops21h 38m

$3,410

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
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See travel insights to Kingston from

How to get the cheapest flight ticket from Chicago Midway Airport to Kingston

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Kingston?

Our data shows that Tuesday is the least expensive day to fly to Kingston. Tickets to fly out on this day can be as low as $450. The most expensive day to fly to Kingston is Sunday, with ticket prices averaging around $694.

What is the cheapest time of day to depart on your flight to Kingston?

The cheapest time of day to fly to Kingston is in the evening when flights can be purchased for as low as $349. In the afternoon is when there is more demand to fly to Kingston, so prices are often more expensive at around $618 per ticket.

When to book flights from Chicago Midway Airport to Kingston

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Kingston according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Kingston (MDW to KIN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Kingston

Direct flights

None
There are no direct flights from Chicago Midway Airport to Kingston. There are no popular flight routes from Chicago Midway Airport to Kingston.
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  • How far is Chicago Midway to Kingston Norman Manley by plane?

    The distance between Chicago Midway and Kingston Norman Manley is about 1764.3 mi. Flights usually cover this in 7h 17m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago Midway Airport to Kingston Norman Manley Airport?

    Prices for flights from Chicago Midway Airport to Kingston Norman Manley Airport are updated daily.

  • How old do you have to be to fly from Chicago Midway Airport to Kingston Norman Manley Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Kingston Norman Manley Airport.

  • What documentation or ID do you need to fly to Kingston Norman Manley Airport?

    The travel and health documents required for your trip to Kingston Norman Manley Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Kingston Norman Manley Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Kingston?

Book flights to Kingston if you plan to visit one of these locations
Port Antonio

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Kingston?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Kingston from Chicago.

Can I find flights from Chicago to Kingston with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Kingston from Chicago with this policy.

How can momondo help me find flights from Chicago to Kingston?

Once you have performed a search for Chicago to Kingston flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Kingston right now. Can momondo alert me if prices change?

Price alerts on flights to Kingston from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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