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Cheap flights from Chicago Midway Airport to Kingston from $172

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 9/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago Midway Airport to Kingston (MDW-KIN)

Cheap round-trip flights

Delta Logo
6:00 am - 8:00 pmMDW-KIN
13h 00m1 stop
Delta Logo
9:00 am - 11:32 pmKIN-MDW
15h 32m1 stop
$433Delta
Find Deal
Sun, Nov 16 - Thu, Nov 27
Delta Logo
6:48 pm - 8:00 pmMDW-KIN
24h 12m2 stops
Delta Logo
9:00 am - 8:52 amKIN-MDW
24h 52m2 stops
$438Delta
Find Deal
Sun, Nov 16 - Sun, Nov 23
Delta Logo
6:00 am - 8:00 pmMDW-KIN
13h 00m1 stop
Delta Logo
9:00 am - 11:32 pmKIN-MDW
15h 32m1 stop
$517Delta
Find Deal
Sun, Nov 16 - Wed, Nov 26
Delta Logo
12:47 pm - 8:00 pmMDW-KIN
6h 13m1 stop
Delta Logo
9:00 am - 6:08 pmKIN-MDW
10h 08m2 stops
$522Delta
Find Deal
Tue, Nov 18 - Mon, Nov 24
Delta Logo
12:48 pm - 8:00 pmMDW-KIN
7h 12m1 stop
Delta Logo
9:00 am - 4:39 pmKIN-MDW
8h 39m1 stop
$559Delta
Find Deal
Tue, Oct 21 - Mon, Nov 10
Delta Logo
6:00 am - 8:00 pmMDW-KIN
14h 00m1 stop
Delta Logo
9:00 am - 9:36 pmKIN-MDW
12h 36m1 stop
$601Delta
Find Deal
Sat, Sep 20 - Tue, Sep 23
Logo
9:20 am - 2:28 pmMDW-KIN
29h 08m2 stops
Logo
8:05 am - 5:35 pmKIN-MDW
33h 30m3 stops
$1,203
Find Deal
Thu, Sep 18 - Sun, Sep 21
WestJet Logo
1:47 pm - 3:33 pmMDW-KIN
24h 46m2 stops
WestJet Logo
4:30 pm - 6:18 pmKIN-MDW
26h 48m2 stops
$3,300WestJet
Find Deal
Sun, Nov 16 - Mon, Nov 24
WestJet Logo
7:02 pm - 3:33 pmMDW-KIN
43h 31m2 stops
WestJet Logo
4:30 pm - 1:07 pmKIN-MDW
21h 37m2 stops
$3,337WestJet
Find Deal
Sat, Nov 22 - Fri, Nov 28
WestJet Logo
7:02 pm - 3:33 pmMDW-KIN
43h 31m2 stops
WestJet Logo
4:30 pm - 1:07 pmKIN-MDW
21h 37m2 stops
$3,339WestJet
Find Deal
Wed, Nov 19 - Mon, Nov 24

Delta flights from Chicago Midway Airport to Kingston

Our best Delta deals on Chicago Midway Airport to Kingston flight tickets
Delta
Nov 16
MDW6:00 amChicago Midway
13h 00m
1 stop
KIN8:00 pmKingston Norman Manley
Nov 27
KIN9:00 amKingston Norman Manley
15h 32m
1 stop
MDW11:32 pmChicago Midway
$433
Find similar
Delta
Nov 16
MDW6:48 pmChicago Midway
24h 12m
2 stops
KIN8:00 pmKingston Norman Manley
Nov 23
KIN9:00 amKingston Norman Manley
24h 52m
2 stops
MDW8:52 amChicago Midway
$438
Find similar
Delta
Nov 16
MDW6:00 amChicago Midway
13h 00m
1 stop
KIN8:00 pmKingston Norman Manley
Nov 26
KIN9:00 amKingston Norman Manley
15h 32m
1 stop
MDW11:32 pmChicago Midway
$517
Find similar

WestJet flights from Chicago Midway Airport to Kingston

Our best WestJet deals on Chicago Midway Airport to Kingston flight tickets
WestJet
Nov 16
MDW1:47 pmChicago Midway
24h 46m
2 stops
KIN3:33 pmKingston Norman Manley
Nov 24
KIN4:30 pmKingston Norman Manley
26h 48m
2 stops
MDW6:18 pmChicago Midway
$3,300
Find similar
WestJet
Nov 22
MDW7:02 pmChicago Midway
43h 31m
2 stops
KIN3:33 pmKingston Norman Manley
Nov 28
KIN4:30 pmKingston Norman Manley
21h 37m
2 stops
MDW1:07 pmChicago Midway
$3,337
Find similar
WestJet
Nov 19
MDW7:02 pmChicago Midway
43h 31m
2 stops
KIN3:33 pmKingston Norman Manley
Nov 24
KIN4:30 pmKingston Norman Manley
21h 37m
2 stops
MDW1:07 pmChicago Midway
$3,339
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 7, 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

Sun 11/16

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

Thu 11/27

9:00 am-11:32 pm

1 stop15h 32m

$433

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sun 11/16

6:48 pm-8:00 pm

2 stops24h 12m

Kingston Norman Manley

Sun 11/23

9:00 am-8:52 am

2 stops24h 52m

$438

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sun 11/16

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

Wed 11/26

9:00 am-11:32 pm

1 stop15h 32m

$517

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 11/18

12:47 pm-8:00 pm

1 stop6h 13m

Kingston Norman Manley

Mon 11/24

9:00 am-6:08 pm

2 stops10h 08m

$522

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 10/21

12:48 pm-8:00 pm

1 stop7h 12m

Kingston Norman Manley

Mon 11/10

9:00 am-4:39 pm

1 stop8h 39m

$559

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 9/20

6:00 am-8:00 pm

1 stop14h 00m

Kingston Norman Manley

Tue 9/23

9:00 am-9:36 pm

1 stop12h 36m

$601

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 9/18

9:20 am-2:28 pm

2 stops29h 08m

Kingston Norman Manley

Sun 9/21

8:05 am-5:35 pm

3 stops33h 30m

$1,203

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sun 11/16

1:47 pm-3:33 pm

2 stops24h 46m

Kingston Norman Manley

Mon 11/24

4:30 pm-6:18 pm

2 stops26h 48m

$3,300

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 11/22

7:02 pm-3:33 pm

2 stops43h 31m

Kingston Norman Manley

Fri 11/28

4:30 pm-1:07 pm

2 stops21h 37m

$3,337

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 11/19

7:02 pm-3:33 pm

2 stops43h 31m

Kingston Norman Manley

Mon 11/24

4:30 pm-1:07 pm

2 stops21h 37m

$3,339

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 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 6h 13m, 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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