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Cheap flights from Chicago to Kingston from $182

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 to Kingston departing on 12/14. 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 to Kingston

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
5:10 am - 12:01 pmORD-KIN
5h 51m1 stop
Spirit Airlines Logo
2:24 pm - 11:13 pmKIN-ORD
9h 49m1 stop
$352Spirit Airlines
Find Deal
Wed, Nov 19 - Thu, Nov 20
Spirit Airlines Logo
3:43 pm - 12:14 pmORD-KIN
19h 31m1 stop
Spirit Airlines Logo
1:19 pm - 8:01 pmKIN-ORD
7h 42m1 stop
$353Spirit Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
Multiple Airlines Logo
5:00 am - 1:21 pmORD-KIN
7h 21m1 stop
Multiple Airlines Logo
1:19 pm - 1:57 pmKIN-ORD
25h 38m1 stop
$357Multiple Airlines
Find Deal
Tue, Dec 2 - Wed, Dec 10
Multiple Airlines Logo
11:42 am - 12:13 pmORD-KIN
23h 31m1 stop
Multiple Airlines Logo
1:28 pm - 9:23 amKIN-ORD
20h 55m1 stop
$362Multiple Airlines
Find Deal
Thu, Jan 22 - Tue, Jan 27
Spirit Airlines Logo
5:00 am - 12:14 pmORD-KIN
6h 14m1 stop
Spirit Airlines Logo
1:19 pm - 12:09 amKIN-ORD
11h 50m1 stop
$372Spirit Airlines
Find Deal
Wed, Dec 10 - Fri, Dec 12
American Airlines Logo
2:40 pm - 10:34 pmORD-KIN
6h 54m1 stop
American Airlines Logo
7:00 am - 6:07 pmKIN-ORD
12h 07m1 stop
$434American Airlines
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Fri, Dec 5 - Thu, Dec 11
Delta Logo
6:00 am - 8:00 pmMDW-KIN
13h 00m1 stop
Delta Logo
9:00 am - 3:40 pmKIN-MDW
7h 40m1 stop
$445Delta
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Sat, Jan 31 - Sat, Feb 7
Delta Logo
9:34 am - 8:00 pmMDW-KIN
9h 26m2 stops
Delta Logo
9:00 am - 3:40 pmKIN-MDW
7h 40m1 stop
$450Delta
Find Deal
Sat, Jan 31 - Sat, Feb 7
WestJet Logo
7:02 pm - 3:33 pmMDW-KIN
19h 31m3 stops
WestJet Logo
4:30 pm - 6:32 pmKIN-MDW
27h 02m2 stops
$1,790WestJet
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Mon, Dec 15 - Mon, Jan 5
WestJet Logo
7:02 pm - 3:33 pmMDW-KIN
19h 31m3 stops
WestJet Logo
4:30 pm - 1:09 pmKIN-MDW
21h 39m3 stops
$1,881WestJet
Find Deal
Mon, Dec 15 - Mon, Jan 5

American Airlines flights from Chicago to Kingston

Our best American Airlines deals on Chicago to Kingston flight tickets
American Airlines
Dec 5
ORD2:40 pmChicago O'Hare Intl
6h 54m
1 stop
KIN10:34 pmKingston Norman Manley
Dec 11
KIN7:00 amKingston Norman Manley
12h 07m
1 stop
ORD6:07 pmChicago O'Hare Intl
$434
Find similar
American Airlines
Nov 9
ORD5:00 amChicago O'Hare Intl
16h 13m
1 stop
KIN10:13 pmKingston Norman Manley
Dec 3
KIN1:42 pmKingston Norman Manley
10h 15m
1 stop
ORD10:57 pmChicago O'Hare Intl
$562
Find similar
American Airlines
Nov 9
ORD10:25 amChicago O'Hare Intl
10h 48m
1 stop
KIN10:13 pmKingston Norman Manley
Dec 3
KIN1:42 pmKingston Norman Manley
10h 57m
2 stops
ORD11:39 pmChicago O'Hare Intl
$566
Find similar

Spirit Airlines flights from Chicago to Kingston

Our best Spirit Airlines deals on Chicago to Kingston flight tickets
Spirit Airlines
Nov 19
ORD5:10 amChicago O'Hare Intl
5h 51m
1 stop
KIN12:01 pmKingston Norman Manley
Nov 20
KIN2:24 pmKingston Norman Manley
9h 49m
1 stop
ORD11:13 pmChicago O'Hare Intl
$352
Find similar
Spirit Airlines
Dec 3
ORD3:43 pmChicago O'Hare Intl
19h 31m
1 stop
KIN12:14 pmKingston Norman Manley
Dec 10
KIN1:19 pmKingston Norman Manley
7h 42m
1 stop
ORD8:01 pmChicago O'Hare Intl
$353
Find similar
Spirit Airlines
Dec 10
ORD5:00 amChicago O'Hare Intl
6h 14m
1 stop
KIN12:14 pmKingston Norman Manley
Dec 12
KIN1:19 pmKingston Norman Manley
11h 50m
1 stop
ORD12:09 amChicago O'Hare Intl
$372
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 3, 2025.
Use the filters below to find and compare flights from Chicago to Kingston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 11/19

5:10 am-12:01 pm

1 stop5h 51m

Kingston Norman Manley

Thu 11/20

2:24 pm-11:13 pm

1 stop9h 49m

$352

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 12/3

3:43 pm-12:14 pm

1 stop19h 31m

Kingston Norman Manley

Wed 12/10

1:19 pm-8:01 pm

1 stop7h 42m

$353

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 12/2

5:00 am-1:21 pm

1 stop7h 21m

Kingston Norman Manley

Wed 12/10

1:19 pm-1:57 pm

1 stop25h 38m

$357

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 1/22

11:42 am-12:13 pm

1 stop23h 31m

Kingston Norman Manley

Tue 1/27

1:28 pm-9:23 am

1 stop20h 55m

$362

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 12/10

5:00 am-12:14 pm

1 stop6h 14m

Kingston Norman Manley

Fri 12/12

1:19 pm-12:09 am

1 stop11h 50m

$372

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 12/5

2:40 pm-10:34 pm

1 stop6h 54m

Kingston Norman Manley

Thu 12/11

7:00 am-6:07 pm

1 stop12h 07m

$434

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 1/31

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

Sat 2/7

9:00 am-3:40 pm

1 stop7h 40m

$445

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 1/31

9:34 am-8:00 pm

2 stops9h 26m

Kingston Norman Manley

Sat 2/7

9:00 am-3:40 pm

1 stop7h 40m

$450

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 12/15

7:02 pm-3:33 pm

3 stops19h 31m

Kingston Norman Manley

Mon 1/5

4:30 pm-6:32 pm

2 stops27h 02m

$1,790

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 12/15

7:02 pm-3:33 pm

3 stops19h 31m

Kingston Norman Manley

Mon 1/5

4:30 pm-1:09 pm

3 stops21h 39m

$1,881

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 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 typical price of a round-trip flight between Chicago and Kingston?

What is the cheapest month to fly to Kingston?

In general, February is the cheapest month to fly from Chicago to Kingston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $380. If you aren’t able to travel during the month of February, then book flights to Kingston from Chicago during April instead. Flights to Kingston in April, while not as cheap as those in February, still average around $440.

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 to Kingston

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

Cheap Chicago to Kingston (CHI to KIN) flight deals and tips

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

Direct flights

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

    The straight-line distance from Chicago to Kingston Norman Manley is 1767.3 mi. By plane, this route typically takes 5h 51m.

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

    Prices for flights from Chicago to Kingston Norman Manley Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago to Kingston Norman Manley Airport?

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Kingston Norman Manley Airport.

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

    The travel and health documents you'll need for your trip to Kingston Norman Manley Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Kingston Norman Manley Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago to Kingston?

Best airlines flying from Chicago to Kingston

Compare and see reviews for airlines that fly from Chicago to Kingston with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $310Free CancellationRating
6.3
8,114 reviews
Search Spirit Airlines flights
DeltaPriceFrom $369Free CancellationRating
7.9
8,001 reviews
Search Delta flights
American AirlinesPriceFrom $433Free CancellationRating
7.2
11,036 reviews
Search American Airlines flights

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?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Kingston for you.

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

momondo does allow users to show only those flights to Kingston from Chicago which offer a flexible booking policy as well as other useful filters and features.

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?

Yes momondo offers price alerts on flights to Kingston from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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