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Cheap flights from Chicago Midway Airport to Kingston from $174

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 2/25. 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

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 8:00 pm
MDW
-
KIN
13h 00m
1 stop
Delta Logo
9:00 am - 10:31 pm
KIN
-
MDW
14h 31m
1 stop
$466Delta
Mon, Feb 23 - Mon, Mar 2
Delta Logo
9:35 am - 8:00 pm
MDW
-
KIN
10h 25m
2 stops
Delta Logo
9:00 am - 5:54 pm
KIN
-
MDW
8h 54m
2 stops
$471Delta
Wed, Mar 11 - Wed, Mar 18
Delta Logo
12:45 pm - 8:00 pm
MDW
-
KIN
6h 15m
1 stop
Delta Logo
9:00 am - 5:22 pm
KIN
-
MDW
8h 22m
1 stop
$550Delta
Wed, Mar 4 - Wed, Mar 11
Delta Logo
9:34 am - 8:00 pm
MDW
-
KIN
9h 26m
2 stops
Delta Logo
9:00 am - 5:22 pm
KIN
-
MDW
8h 22m
1 stop
$555Delta
Wed, Mar 4 - Wed, Mar 11
Multiple Airlines Logo
11:05 am - 2:30 pm
MDW
-
KIN
26h 25m
1 stop
Multiple Airlines Logo
1:17 pm - 10:29 pm
KIN
-
MDW
10h 12m
2 stops
$570Multiple Airlines
Mon, Feb 23 - Mon, Mar 2
Multiple Airlines Logo
11:00 am - 1:30 pm
MDW
-
KIN
26h 30m
1 stop
Multiple Airlines Logo
12:17 pm - 10:19 pm
KIN
-
MDW
10h 02m
2 stops
$578Multiple Airlines
Fri, Mar 27 - Tue, Apr 7
Multiple Airlines Logo
9:51 pm - 11:00 am
MDW
-
KIN
13h 09m
2 stops
Multiple Airlines Logo
2:30 pm - 10:05 am
KIN
-
MDW
19h 35m
1 stop
$590Multiple Airlines
Mon, Mar 30 - Tue, Apr 7
Delta Logo
6:00 am - 8:00 pm
MDW
-
KIN
13h 00m
1 stop
Delta Logo
9:00 am - 5:45 pm
KIN
-
MDW
9h 45m
1 stop
$594Delta
Fri, Feb 6 - Thu, Feb 19
Multiple Airlines Logo
9:51 pm - 11:00 am
MDW
-
KIN
13h 09m
2 stops
Multiple Airlines Logo
3:30 pm - 10:05 am
KIN
-
MDW
18h 35m
1 stop
$599Multiple Airlines
Mon, Mar 30 - Mon, Apr 6
Multiple Airlines Logo
9:51 pm - 11:00 am
MDW
-
KIN
13h 09m
2 stops
Multiple Airlines Logo
2:30 pm - 10:05 am
KIN
-
MDW
19h 35m
1 stop
$603Multiple Airlines
Mon, Mar 30 - Sat, Apr 4

Delta flights from Chicago Midway Airport to Kingston

Our best Delta deals on Chicago Midway Airport to Kingston flight tickets
Delta
Feb 23
MDW6:00 amChicago Midway
13h 00m
1 stop
KIN8:00 pmKingston Norman Manley
Mar 2
KIN9:00 amKingston Norman Manley
14h 31m
1 stop
MDW10:31 pmChicago Midway
$466
Delta
Mar 11
MDW6:00 amChicago Midway
14h 00m
1 stop
KIN8:00 pmKingston Norman Manley
Mar 18
KIN9:00 amKingston Norman Manley
8h 54m
2 stops
MDW5:54 pmChicago Midway
$471
Delta
Mar 4
MDW12:45 pmChicago Midway
6h 15m
1 stop
KIN8:00 pmKingston Norman Manley
Mar 11
KIN9:00 amKingston Norman Manley
8h 22m
1 stop
MDW5:22 pmChicago Midway
$550

WestJet flights from Chicago Midway Airport to Kingston

Our best WestJet deals on Chicago Midway Airport to Kingston flight tickets
WestJet
Feb 2
MDW6:35 pmChicago Midway
19h 55m
2 stops
KIN3:30 pmKingston Norman Manley
Feb 6
KIN4:30 pmKingston Norman Manley
21h 16m
2 stops
MDW12:46 pmChicago Midway
$3,416
WestJet
Feb 4
MDW6:35 pmChicago Midway
43h 55m
2 stops
KIN3:30 pmKingston Norman Manley
Feb 11
KIN4:30 pmKingston Norman Manley
21h 16m
2 stops
MDW12:46 pmChicago Midway
$3,419
WestJet
Feb 2
MDW1:26 pmChicago Midway
25h 04m
2 stops
KIN3:30 pmKingston Norman Manley
Feb 6
KIN4:30 pmKingston Norman Manley
21h 16m
2 stops
MDW12:46 pmChicago Midway
$3,425

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 January 27, 2026.
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 2/23

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

Mon 3/2

9:00 am-10:31 pm

1 stop14h 31m

$466

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 3/11

9:35 am-8:00 pm

2 stops10h 25m

Kingston Norman Manley

Wed 3/18

9:00 am-5:54 pm

2 stops8h 54m

$471

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 3/4

12:45 pm-8:00 pm

1 stop6h 15m

Kingston Norman Manley

Wed 3/11

9:00 am-5:22 pm

1 stop8h 22m

$550

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 3/4

9:34 am-8:00 pm

2 stops9h 26m

Kingston Norman Manley

Wed 3/11

9:00 am-5:22 pm

1 stop8h 22m

$555

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 2/23

11:05 am-2:30 pm

1 stop26h 25m

Kingston Norman Manley

Mon 3/2

1:17 pm-10:29 pm

2 stops10h 12m

$570

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 3/27

11:00 am-1:30 pm

1 stop26h 30m

Kingston Norman Manley

Tue 4/7

12:17 pm-10:19 pm

2 stops10h 02m

$578

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 3/30

9:51 pm-11:00 am

2 stops13h 09m

Kingston Norman Manley

Tue 4/7

2:30 pm-10:05 am

1 stop19h 35m

$590

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 2/6

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

Thu 2/19

9:00 am-5:45 pm

1 stop9h 45m

$594

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 3/30

9:51 pm-11:00 am

2 stops13h 09m

Kingston Norman Manley

Mon 4/6

3:30 pm-10:05 am

1 stop18h 35m

$599

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 3/30

9:51 pm-11:00 am

2 stops13h 09m

Kingston Norman Manley

Sat 4/4

2:30 pm-10:05 am

1 stop19h 35m

$603

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 airline that flies from Chicago Midway to Kingston Norman Manley?

Delta is the most popular carrier operating from Chicago Midway to Kingston Norman Manley

What airlines fly to Kingston?

Southwest, Delta and Frontier are the top three most popular airlines that fly to Kingston from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 72% of people opting to fly with this airline when traveling to Kingston. Keep in mind that there are 3 different airlines that fly to Kingston on a routine basis, so you have a few additional options to choose from.

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

Fastest flight time

7h 13m

Direct flights

None
The fastest flight from Chicago Midway Airport to Kingston takes 7h 13m
There are no direct flights from Chicago Midway Airport to Kingston. There are no popular flight routes from Chicago Midway Airport to Kingston.
Search flight deals

  • 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 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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