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Cheap flights from Chicago to Kingston from $157

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 5/11. 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
4:36 pm - 11:35 am
ORD
-
KIN
18h 59m
1 stop
Spirit Airlines Logo
3:18 pm - 9:36 am
KIN
-
ORD
18h 18m
1 stop
$409Spirit Airlines
Mon, Apr 13 - Mon, Apr 27
Spirit Airlines Logo
11:25 am - 11:35 am
ORD
-
KIN
24h 10m
2 stops
Spirit Airlines Logo
3:18 pm - 9:36 am
KIN
-
ORD
18h 18m
1 stop
$426Spirit Airlines
Mon, Apr 13 - Mon, Apr 27
Multiple Airlines Logo
5:05 am - 2:12 pm
ORD
-
KIN
9h 07m
1 stop
Multiple Airlines Logo
3:05 pm - 9:05 am
KIN
-
ORD
18h 00m
1 stop
$443Multiple Airlines
Wed, May 13 - Wed, May 20
Multiple Airlines Logo
5:05 am - 2:12 pm
ORD
-
KIN
9h 07m
1 stop
Multiple Airlines Logo
3:05 pm - 7:45 am
KIN
-
ORD
16h 40m
2 stops
$444Multiple Airlines
Wed, May 13 - Wed, May 20
Spirit Airlines Logo
11:25 am - 11:35 am
ORD
-
KIN
24h 10m
2 stops
Spirit Airlines Logo
3:18 pm - 10:23 am
KIN
-
ORD
19h 05m
2 stops
$451Spirit Airlines
Mon, Apr 13 - Mon, Apr 27
Multiple Airlines Logo
5:05 am - 2:12 pm
ORD
-
KIN
9h 07m
1 stop
Multiple Airlines Logo
3:18 pm - 7:55 am
KIN
-
ORD
40h 37m
2 stops
$461Multiple Airlines
Mon, Apr 27 - Mon, May 4
Multiple Airlines Logo
5:57 pm - 12:35 pm
ORD
-
KIN
18h 38m
1 stop
Multiple Airlines Logo
3:18 pm - 12:24 am
KIN
-
ORD
9h 06m
1 stop
$462Multiple Airlines
Mon, Apr 27 - Fri, May 1
Air Canada Logo
6:21 pm - 1:55 pm
ORD
-
KIN
43h 34m
2 stops
Air Canada Logo
3:05 pm - 12:11 pm
KIN
-
ORD
21h 06m
2 stops
$469Air Canada
Wed, May 13 - Wed, May 20
Delta Logo
10:41 am - 8:00 pm
MDW
-
KIN
9h 19m
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
10:41 am - 8:00 pm
MDW
-
KIN
9h 19m
1 stop
Delta Logo
9:00 am - 10:28 pm
KIN
-
MDW
13h 28m
1 stop
$626Delta
Mon, Apr 27 - Thu, Apr 30

Air Canada flights from Chicago to Kingston

Our best Air Canada deals on Chicago to Kingston flight tickets
Air Canada
May 13
ORD6:21 pmChicago O'Hare Intl
43h 34m
2 stops
KIN1:55 pmKingston Norman Manley
May 20
KIN3:05 pmKingston Norman Manley
21h 06m
2 stops
ORD12:11 pmChicago O'Hare Intl
$469
Air Canada
Jun 11
ORD9:55 amChicago O'Hare Intl
28h 00m
1 stop
KIN1:55 pmKingston Norman Manley
Jun 17
KIN3:05 pmKingston Norman Manley
45h 06m
2 stops
ORD12:11 pmChicago O'Hare Intl
$588

American Airlines flights from Chicago to Kingston

Our best American Airlines deals on Chicago to Kingston flight tickets
American Airlines
May 15
ORD6:50 amChicago O'Hare Intl
6h 32m
1 stop
KIN1:22 pmKingston Norman Manley
May 23
KIN6:21 amKingston Norman Manley
15h 08m
1 stop
ORD9:29 pmChicago O'Hare Intl
$536
American Airlines
May 14
ORD6:50 amChicago O'Hare Intl
6h 32m
1 stop
KIN1:22 pmKingston Norman Manley
May 17
KIN7:00 amKingston Norman Manley
12h 57m
1 stop
ORD7:57 pmChicago O'Hare Intl
$541
American Airlines
May 14
ORD7:15 amChicago O'Hare Intl
11h 39m
2 stops
KIN6:54 pmKingston Norman Manley
May 17
KIN7:00 amKingston Norman Manley
12h 57m
1 stop
ORD7:57 pmChicago O'Hare Intl
$546

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 March 17, 2026.
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

Cheapest round-trip

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 4/13

4:36 pm-11:35 am

1 stop18h 59m

Kingston Norman Manley

Mon 4/27

3:18 pm-9:36 am

1 stop18h 18m

$409

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 4/13

11:25 am-11:35 am

2 stops24h 10m

Kingston Norman Manley

Mon 4/27

3:18 pm-9:36 am

1 stop18h 18m

$426

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 5/13

5:05 am-2:12 pm

1 stop9h 07m

Kingston Norman Manley

Wed 5/20

3:05 pm-9:05 am

1 stop18h 00m

$443

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 5/13

5:05 am-2:12 pm

1 stop9h 07m

Kingston Norman Manley

Wed 5/20

3:05 pm-7:45 am

2 stops16h 40m

$444

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 4/13

11:25 am-11:35 am

2 stops24h 10m

Kingston Norman Manley

Mon 4/27

3:18 pm-10:23 am

2 stops19h 05m

$451

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 4/27

5:05 am-2:12 pm

1 stop9h 07m

Kingston Norman Manley

Mon 5/4

3:18 pm-7:55 am

2 stops40h 37m

$461

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 4/27

5:57 pm-12:35 pm

1 stop18h 38m

Kingston Norman Manley

Fri 5/1

3:18 pm-12:24 am

1 stop9h 06m

$462

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 5/13

6:21 pm-1:55 pm

2 stops43h 34m

Kingston Norman Manley

Wed 5/20

3:05 pm-12:11 pm

2 stops21h 06m

$469
Quickest round-trip

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 4/27

10:41 am-8:00 pm

1 stop9h 19m

Kingston Norman Manley

Thu 4/30

9:00 am-10:28 pm

1 stop13h 28m

$556

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 4/27

10:41 am-8:00 pm

1 stop9h 19m

Kingston Norman Manley

Thu 4/30

9:00 am-10:28 pm

1 stop13h 28m

$626

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, April 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 $440. If you aren’t able to travel during the month of April, then book flights to Kingston from Chicago during August instead. Flights to Kingston in August, while not as cheap as those in April, still average around $471.

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

Fastest flight time

9h 01m

Direct flights

None
The fastest flight from Chicago to Kingston takes 9h 01m
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 9h 01m.

  • 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 $100Free CancellationRating
6.3
8,520 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $433Free CancellationRating
7.1
11,466 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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