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Cheap flights from Chicago to Kingston from $145

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 10/19. 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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0 bags

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Find the cheapest flights from Chicago to Kingston

Cheap round-trip flights

Spirit Airlines Logo
5:59 pm - 12:13 pmORD-KIN
17h 14m1 stop
Spirit Airlines Logo
1:28 pm - 11:42 pmKIN-ORD
11h 14m1 stop
$342Spirit Airlines
Find Deal
Sat, Nov 8 - Thu, Nov 13
Spirit Airlines Logo
6:00 pm - 11:09 amORD-KIN
17h 09m2 stops
Spirit Airlines Logo
12:14 pm - 11:45 pmKIN-ORD
11h 31m1 stop
$373Spirit Airlines
Find Deal
Sat, Oct 11 - Sun, Oct 19
Spirit Airlines Logo
7:43 pm - 11:09 amORD-KIN
15h 26m1 stop
Spirit Airlines Logo
12:14 pm - 11:45 pmKIN-ORD
11h 31m1 stop
$376Spirit Airlines
Find Deal
Sat, Oct 11 - Sun, Oct 19
Spirit Airlines Logo
7:43 pm - 11:09 amORD-KIN
15h 26m1 stop
Spirit Airlines Logo
1:28 pm - 9:00 pmKIN-ORD
8h 32m1 stop
$381Spirit Airlines
Find Deal
Wed, Oct 29 - Wed, Nov 5
Spirit Airlines Logo
7:43 pm - 11:09 amORD-KIN
15h 26m1 stop
Spirit Airlines Logo
12:14 pm - 11:45 pmKIN-ORD
11h 31m1 stop
$382Spirit Airlines
Find Deal
Thu, Oct 16 - Mon, Oct 20
Spirit Airlines Logo
7:43 pm - 11:09 amORD-KIN
15h 26m1 stop
Spirit Airlines Logo
12:14 pm - 1:03 amKIN-ORD
12h 49m1 stop
$386Spirit Airlines
Find Deal
Wed, Oct 15 - Sun, Oct 26
Logo
7:43 pm - 11:09 amORD-KIN
15h 26m1 stop
Logo
7:55 am - 6:38 pmKIN-ORD
10h 43m1 stop
$407
Find Deal
Wed, Oct 22 - Sat, Oct 25
Delta Logo
12:48 pm - 8:00 pmMDW-KIN
7h 12m1 stop
Delta Logo
9:00 am - 10:14 pmKIN-MDW
13h 14m1 stop
$433Delta
Find Deal
Sun, Oct 12 - Sun, Oct 19
Delta Logo
1:18 pm - 8:00 pmORD-KIN
6h 42m1 stop
Delta Logo
9:00 am - 11:59 pmKIN-ORD
14h 59m1 stop
$433Delta
Find Deal
Sat, Oct 11 - Sun, Oct 19
Delta Logo
6:00 am - 8:00 pmMDW-KIN
14h 00m1 stop
Delta Logo
10:00 am - 6:25 pmKIN-MDW
9h 25m2 stops
$438Delta
Find Deal
Wed, Oct 29 - Wed, Nov 5

Spirit Airlines flights from Chicago to Kingston

Our best Spirit Airlines deals on Chicago to Kingston flight tickets
Spirit Airlines
Nov 8
ORD5:59 pmChicago O'Hare Intl
17h 14m
1 stop
KIN12:13 pmKingston Norman Manley
Nov 13
KIN1:28 pmKingston Norman Manley
11h 14m
1 stop
ORD11:42 pmChicago O'Hare Intl
$342
Find similar
Spirit Airlines
Oct 11
ORD6:00 pmChicago O'Hare Intl
17h 09m
2 stops
KIN11:09 amKingston Norman Manley
Oct 19
KIN12:14 pmKingston Norman Manley
11h 31m
1 stop
ORD11:45 pmChicago O'Hare Intl
$373
Find similar
Spirit Airlines
Oct 11
ORD7:43 pmChicago O'Hare Intl
15h 26m
1 stop
KIN11:09 amKingston Norman Manley
Oct 19
KIN12:14 pmKingston Norman Manley
11h 31m
1 stop
ORD11:45 pmChicago O'Hare Intl
$376
Find similar

Delta flights from Chicago to Kingston

Our best Delta deals on Chicago to Kingston flight tickets
Delta
Oct 12
MDW12:48 pmChicago Midway
7h 12m
1 stop
KIN8:00 pmKingston Norman Manley
Oct 19
KIN9:00 amKingston Norman Manley
13h 14m
1 stop
MDW10:14 pmChicago Midway
$433
Find similar
Delta
Oct 29
MDW6:00 amChicago Midway
14h 00m
1 stop
KIN8:00 pmKingston Norman Manley
Nov 5
KIN10:00 amKingston Norman Manley
9h 25m
2 stops
MDW6:25 pmChicago Midway
$438
Find similar
Delta
Feb 21
MDW6:00 amChicago Midway
13h 00m
1 stop
KIN8:00 pmKingston Norman Manley
Feb 28
KIN9:00 amKingston Norman Manley
7h 25m
1 stop
MDW3:25 pmChicago Midway
$445
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 September 15, 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

Sat 11/8

5:59 pm-12:13 pm

1 stop17h 14m

Kingston Norman Manley

Thu 11/13

1:28 pm-11:42 pm

1 stop11h 14m

$342

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 10/11

6:00 pm-11:09 am

2 stops17h 09m

Kingston Norman Manley

Sun 10/19

12:14 pm-11:45 pm

1 stop11h 31m

$373

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 10/11

7:43 pm-11:09 am

1 stop15h 26m

Kingston Norman Manley

Sun 10/19

12:14 pm-11:45 pm

1 stop11h 31m

$376

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 10/29

7:43 pm-11:09 am

1 stop15h 26m

Kingston Norman Manley

Wed 11/5

1:28 pm-9:00 pm

1 stop8h 32m

$381

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 10/16

7:43 pm-11:09 am

1 stop15h 26m

Kingston Norman Manley

Mon 10/20

12:14 pm-11:45 pm

1 stop11h 31m

$382

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 10/15

7:43 pm-11:09 am

1 stop15h 26m

Kingston Norman Manley

Sun 10/26

12:14 pm-1:03 am

1 stop12h 49m

$386

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 10/22

7:43 pm-11:09 am

1 stop15h 26m

Kingston Norman Manley

Sat 10/25

7:55 am-6:38 pm

1 stop10h 43m

$407

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sun 10/12

12:48 pm-8:00 pm

1 stop7h 12m

Kingston Norman Manley

Sun 10/19

9:00 am-10:14 pm

1 stop13h 14m

$433

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 10/11

1:18 pm-8:00 pm

1 stop6h 42m

Kingston Norman Manley

Sun 10/19

9:00 am-11:59 pm

1 stop14h 59m

$433

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 10/29

6:00 am-8:00 pm

1 stop14h 00m

Kingston Norman Manley

Wed 11/5

10:00 am-6:25 pm

2 stops9h 25m

$438

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 September instead. Flights to Kingston in September, while not as cheap as those in February, still average around $414.

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.
Search flight deals

  • 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 55m.

  • 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
DeltaPriceFrom $295Free CancellationRating
7.9
7,954 reviews
Search Delta flights
Spirit AirlinesPriceFrom $310Free CancellationRating
6.3
8,015 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $450Free CancellationRating
7.2
10,000 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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