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Cheap flights from Chicago Midway Airport to Kingston from $270

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 4/14. 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
12:52 pm - 8:00 pm
MDW
-
KIN
7h 08m
1 stop
Delta Logo
9:00 am - 10:28 pm
KIN
-
MDW
13h 28m
1 stop
$556Delta
Mon, Apr 27 - Thu, Apr 30
Delta Logo
6:23 am - 8:00 pm
MDW
-
KIN
13h 37m
1 stop
Delta Logo
9:00 am - 4:12 pm
KIN
-
MDW
7h 12m
1 stop
$640Delta
Sun, May 31 - Tue, Jun 2
Delta Logo
9:22 am - 8:00 pm
MDW
-
KIN
10h 38m
2 stops
Delta Logo
9:00 am - 9:09 pm
KIN
-
MDW
12h 09m
1 stop
$645Delta
Mon, May 11 - Fri, May 15
Multiple Airlines Logo
12:27 pm - 11:07 am
MDW
-
KIN
22h 40m
2 stops
Multiple Airlines Logo
6:25 pm - 2:35 pm
KIN
-
MDW
20h 10m
1 stop
$646Multiple Airlines
Tue, May 26 - Wed, Jun 3
Multiple Airlines Logo
6:00 am - 2:12 pm
MDW
-
KIN
8h 12m
2 stops
Multiple Airlines Logo
6:25 pm - 9:45 am
KIN
-
MDW
15h 20m
1 stop
$693Multiple Airlines
Mon, Apr 27 - Fri, May 1
Multiple Airlines Logo
3:20 pm - 2:30 pm
MDW
-
KIN
23h 10m
1 stop
Multiple Airlines Logo
6:25 pm - 2:35 pm
KIN
-
MDW
20h 10m
1 stop
$695Multiple Airlines
Tue, May 26 - Wed, Jun 3
Multiple Airlines Logo
6:00 am - 2:12 pm
MDW
-
KIN
8h 12m
2 stops
Multiple Airlines Logo
3:30 pm - 9:45 am
KIN
-
MDW
18h 15m
1 stop
$700Multiple Airlines
Mon, Apr 27 - Fri, May 1
Delta Logo
11:05 am - 8:00 pm
MDW
-
KIN
8h 55m
1 stop
Delta Logo
9:00 am - 4:16 pm
KIN
-
MDW
7h 16m
1 stop
$724Delta
Thu, Jun 11 - Wed, Jun 17
Delta Logo
9:17 am - 8:00 pm
MDW
-
KIN
10h 43m
2 stops
Delta Logo
9:00 am - 4:16 pm
KIN
-
MDW
7h 16m
1 stop
$729Delta
Thu, Jun 11 - Wed, Jun 17
Delta Logo
12:47 pm - 8:00 pm
MDW
-
KIN
7h 13m
1 stop
Delta Logo
9:00 am - 10:28 pm
KIN
-
MDW
13h 28m
1 stop
$768Delta
Wed, Apr 8 - Sat, Apr 18

Delta flights from Chicago Midway Airport to Kingston

Our best Delta deals on Chicago Midway Airport to Kingston flight tickets
Delta
Apr 27
MDW12:52 pmChicago Midway
7h 08m
1 stop
KIN8:00 pmKingston Norman Manley
Apr 30
KIN9:00 amKingston Norman Manley
13h 28m
1 stop
MDW10:28 pmChicago Midway
$556
Delta
May 31
MDW6:23 amChicago Midway
13h 37m
1 stop
KIN8:00 pmKingston Norman Manley
Jun 2
KIN9:00 amKingston Norman Manley
7h 12m
1 stop
MDW4:12 pmChicago Midway
$640
Delta
May 11
MDW9:22 amChicago Midway
10h 38m
2 stops
KIN8:00 pmKingston Norman Manley
May 15
KIN9:00 amKingston Norman Manley
12h 09m
1 stop
MDW9:09 pmChicago Midway
$645

WestJet flights from Chicago Midway Airport to Kingston

Our best WestJet deals on Chicago Midway Airport to Kingston flight tickets
WestJet
Apr 8
MDW1:10 pmChicago Midway
25h 20m
2 stops
KIN2:30 pmKingston Norman Manley
Apr 14
KIN4:30 pmKingston Norman Manley
16h 17m
2 stops
MDW8:47 amChicago Midway
$3,982
WestJet
Apr 8
MDW6:34 pmChicago Midway
19h 56m
2 stops
KIN2:30 pmKingston Norman Manley
Apr 13
KIN3:30 pmKingston Norman Manley
21h 13m
2 stops
MDW12:43 pmChicago Midway
$4,056

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 March 26, 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

Cheapest round-trip

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 4/27

12:52 pm-8:00 pm

1 stop7h 08m

Kingston Norman Manley

Thu 4/30

9:00 am-10:28 pm

1 stop13h 28m

$556

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sun 5/31

6:23 am-8:00 pm

1 stop13h 37m

Kingston Norman Manley

Tue 6/2

9:00 am-4:12 pm

1 stop7h 12m

$640

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 5/11

9:22 am-8:00 pm

2 stops10h 38m

Kingston Norman Manley

Fri 5/15

9:00 am-9:09 pm

1 stop12h 09m

$645

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 5/26

12:27 pm-11:07 am

2 stops22h 40m

Kingston Norman Manley

Wed 6/3

6:25 pm-2:35 pm

1 stop20h 10m

$646

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 4/27

6:00 am-2:12 pm

2 stops8h 12m

Kingston Norman Manley

Fri 5/1

6:25 pm-9:45 am

1 stop15h 20m

$693

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 5/26

3:20 pm-2:30 pm

1 stop23h 10m

Kingston Norman Manley

Wed 6/3

6:25 pm-2:35 pm

1 stop20h 10m

$695

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 4/27

6:00 am-2:12 pm

2 stops8h 12m

Kingston Norman Manley

Fri 5/1

3:30 pm-9:45 am

1 stop18h 15m

$700
Quickest round-trip

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 6/11

11:05 am-8:00 pm

1 stop8h 55m

Kingston Norman Manley

Wed 6/17

9:00 am-4:16 pm

1 stop7h 16m

$724

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 6/11

9:17 am-8:00 pm

2 stops10h 43m

Kingston Norman Manley

Wed 6/17

9:00 am-4:16 pm

1 stop7h 16m

$729

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 4/8

12:47 pm-8:00 pm

1 stop7h 13m

Kingston Norman Manley

Sat 4/18

9:00 am-10:28 pm

1 stop13h 28m

$768

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 airline that flies from Chicago Midway to Kingston Norman Manley?

WestJet and Delta are the most popular carriers operating from Chicago Midway to Kingston Norman Manley

What airlines fly to Kingston?

Southwest, Frontier and Delta 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 70% 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

6h 59m

Direct flights

None
The fastest flight from Chicago Midway Airport to Kingston takes 6h 59m
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 6h 59m, 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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