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Cheap flights from Chicago Midway Airport to Kingston from $445

This is the cheapest round-trip 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 1/23. 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

Enter your travel dates to find the best prices.
Delta Logo
10:48 am - 8:00 pmMDW-KIN
8h 12m1 stop
Delta Logo
9:00 am - 3:38 pmKIN-MDW
7h 38m1 stop
$445Delta
Find Deal
Fri, Jan 23 - Sat, Jan 31
Delta Logo
9:32 am - 8:00 pmMDW-KIN
9h 28m2 stops
Delta Logo
9:00 am - 10:22 pmKIN-MDW
14h 22m1 stop
$450Delta
Find Deal
Fri, Jan 23 - Sat, Jan 31
Multiple Airlines Logo
5:10 pm - 12:12 pmMDW-KIN
18h 02m2 stops
Multiple Airlines Logo
3:30 pm - 3:20 pmKIN-MDW
24h 50m1 stop
$455Multiple Airlines
Find Deal
Wed, Jan 7 - Sat, Jan 10
Delta Logo
6:00 am - 8:00 pmMDW-KIN
13h 00m1 stop
Delta Logo
9:00 am - 3:38 pmKIN-MDW
7h 38m1 stop
$529Delta
Find Deal
Fri, Jan 23 - Sat, Jan 31
Delta Logo
9:32 am - 8:00 pmMDW-KIN
9h 28m2 stops
Delta Logo
9:00 am - 10:22 pmKIN-MDW
14h 22m1 stop
$534Delta
Find Deal
Fri, Jan 23 - Sat, Jan 31
Delta Logo
6:00 am - 8:00 pmMDW-KIN
13h 00m1 stop
Delta Logo
9:00 am - 5:45 pmKIN-MDW
9h 45m1 stop
$613Delta
Find Deal
Thu, Feb 26 - Mon, Mar 2
Delta Logo
9:30 am - 8:05 pmMDW-KIN
10h 35m2 stops
Delta Logo
9:00 am - 9:45 pmKIN-MDW
12h 45m1 stop
$618Delta
Find Deal
Sun, May 10 - Sat, May 16
Multiple Airlines Logo
8:15 am - 12:14 pmMDW-KIN
26h 59m2 stops
Multiple Airlines Logo
3:15 am - 3:20 pmKIN-MDW
13h 05m1 stop
$635Multiple Airlines
Find Deal
Mon, Dec 29 - Thu, Jan 1
Delta Logo
11:21 am - 8:00 pmMDW-KIN
7h 39m1 stop
Delta Logo
9:00 am - 3:38 pmKIN-MDW
7h 38m1 stop
$638Delta
Find Deal
Sat, Jan 10 - Sat, Jan 31
Delta Logo
6:00 am - 8:05 pmMDW-KIN
14h 05m1 stop
Delta Logo
9:00 am - 6:31 pmKIN-MDW
9h 31m2 stops
$643Delta
Find Deal
Sun, May 3 - Sat, May 16

Delta flights from Chicago Midway Airport to Kingston

Our best Delta deals on Chicago Midway Airport to Kingston flight tickets
Delta
Jan 23
MDW10:48 amChicago Midway
8h 12m
1 stop
KIN8:00 pmKingston Norman Manley
Jan 31
KIN9:00 amKingston Norman Manley
7h 38m
1 stop
MDW3:38 pmChicago Midway
$445
Find similar
Delta
Jan 23
MDW9:32 amChicago Midway
9h 28m
2 stops
KIN8:00 pmKingston Norman Manley
Jan 31
KIN9:00 amKingston Norman Manley
14h 22m
1 stop
MDW10:22 pmChicago Midway
$450
Find similar
Delta
Jan 23
MDW6:00 amChicago Midway
13h 00m
1 stop
KIN8:00 pmKingston Norman Manley
Jan 31
KIN9:00 amKingston Norman Manley
7h 38m
1 stop
MDW3:38 pmChicago Midway
$529
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 November 25, 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

Fri 1/23

10:48 am-8:00 pm

1 stop8h 12m

Kingston Norman Manley

Sat 1/31

9:00 am-3:38 pm

1 stop7h 38m

$445

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 1/23

9:32 am-8:00 pm

2 stops9h 28m

Kingston Norman Manley

Sat 1/31

9:00 am-10:22 pm

1 stop14h 22m

$450

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 1/7

5:10 pm-12:12 pm

2 stops18h 02m

Kingston Norman Manley

Sat 1/10

3:30 pm-3:20 pm

1 stop24h 50m

$455

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 1/23

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

Sat 1/31

9:00 am-3:38 pm

1 stop7h 38m

$529

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 1/23

9:32 am-8:00 pm

2 stops9h 28m

Kingston Norman Manley

Sat 1/31

9:00 am-10:22 pm

1 stop14h 22m

$534

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 2/26

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

Mon 3/2

9:00 am-5:45 pm

1 stop9h 45m

$613

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sun 5/10

9:30 am-8:05 pm

2 stops10h 35m

Kingston Norman Manley

Sat 5/16

9:00 am-9:45 pm

1 stop12h 45m

$618

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 12/29

8:15 am-12:14 pm

2 stops26h 59m

Kingston Norman Manley

Thu 1/1

3:15 am-3:20 pm

1 stop13h 05m

$635

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 1/10

11:21 am-8:00 pm

1 stop7h 39m

Kingston Norman Manley

Sat 1/31

9:00 am-3:38 pm

1 stop7h 38m

$638

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sun 5/3

6:00 am-8:05 pm

1 stop14h 05m

Kingston Norman Manley

Sat 5/16

9:00 am-6:31 pm

2 stops9h 31m

$643

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 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

Fastest flight time

9h 30m

Direct flights

None
The fastest flight from Chicago Midway Airport to Kingston takes 9h 30m
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 39m, 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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