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Cheap flights from Kingston to Chicago from $266

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Kingston to Chicago departing on 5/22. 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 Kingston to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
12:41 pm - 12:24 am
KIN
-
ORD
11h 43m
1 stop
American Airlines Logo
5:00 am - 7:54 pm
ORD
-
KIN
14h 54m
1 stop
$378American Airlines
Sat, May 23 - Thu, May 28
American Airlines Logo
6:21 am - 6:11 pm
KIN
-
ORD
11h 50m
2 stops
American Airlines Logo
7:00 am - 7:54 pm
ORD
-
KIN
12h 54m
1 stop
$382American Airlines
Sat, May 23 - Thu, May 28
JetBlue Logo
4:05 pm - 11:44 pm
KIN
-
ORD
7h 39m
1 stop
JetBlue Logo
7:00 am - 12:43 pm
ORD
-
KIN
5h 43m
1 stop
$433JetBlue
Thu, Oct 15 - Thu, Oct 22
American Airlines Logo
6:21 am - 9:29 pm
KIN
-
ORD
15h 08m
1 stop
American Airlines Logo
6:00 pm - 11:41 am
ORD
-
KIN
17h 41m
1 stop
$488American Airlines
Sun, May 24 - Thu, May 28
American Airlines Logo
6:22 am - 11:30 pm
KIN
-
ORD
17h 08m
1 stop
American Airlines Logo
6:00 pm - 11:40 am
ORD
-
KIN
17h 40m
1 stop
$499American Airlines
Sun, Jun 7 - Sat, Jun 13
Air Canada Logo
3:05 pm - 9:00 am
KIN
-
ORD
17h 55m
1 stop
Air Canada Logo
8:20 pm - 1:55 pm
ORD
-
KIN
17h 35m
1 stop
$500Air Canada
Wed, Jun 10 - Sun, Jun 14
Air Canada Logo
3:05 pm - 9:00 am
KIN
-
ORD
17h 55m
1 stop
Air Canada Logo
6:22 pm - 1:55 pm
ORD
-
KIN
19h 33m
2 stops
$505Air Canada
Wed, Jun 10 - Sun, Jun 14
American Airlines Logo
12:42 pm - 12:19 am
KIN
-
ORD
11h 37m
1 stop
American Airlines Logo
5:00 am - 8:09 pm
ORD
-
KIN
15h 09m
1 stop
$510American Airlines
Fri, Jun 26 - Wed, Jul 22
American Airlines Logo
6:22 am - 7:59 pm
KIN
-
ORD
13h 37m
1 stop
American Airlines Logo
9:00 am - 8:09 pm
ORD
-
KIN
11h 09m
2 stops
$514American Airlines
Fri, Jun 26 - Wed, Jul 22
Air Canada Logo
3:05 pm - 6:52 pm
KIN
-
ORD
27h 47m
2 stops
Air Canada Logo
6:22 pm - 1:55 pm
ORD
-
KIN
43h 33m
2 stops
$516Air Canada
Wed, Jun 10 - Sun, Jun 14

JetBlue flights from Kingston to Chicago

Our best JetBlue deals on Kingston to Chicago flight tickets
JetBlue
Oct 15
KIN4:05 pmKingston Norman Manley
7h 39m
1 stop
ORD11:44 pmChicago O'Hare Intl
Oct 22
ORD7:00 amChicago O'Hare Intl
5h 43m
1 stop
KIN12:43 pmKingston Norman Manley
$433
JetBlue
May 27
KIN11:59 pmKingston Norman Manley
9h 55m
1 stop
ORD9:54 amChicago O'Hare Intl
Sep 2
ORD6:00 amChicago O'Hare Intl
17h 47m
1 stop
KIN11:47 pmKingston Norman Manley
$540
JetBlue
May 27
KIN11:59 pmKingston Norman Manley
9h 55m
1 stop
ORD9:54 amChicago O'Hare Intl
Jun 3
ORD6:15 amChicago O'Hare Intl
16h 33m
1 stop
KIN10:48 pmKingston Norman Manley
$549

Air Canada flights from Kingston to Chicago

Our best Air Canada deals on Kingston to Chicago flight tickets
Air Canada
Jun 10
KIN3:05 pmKingston Norman Manley
17h 55m
1 stop
ORD9:00 amChicago O'Hare Intl
Jun 14
ORD8:20 pmChicago O'Hare Intl
17h 35m
1 stop
KIN1:55 pmKingston Norman Manley
$500
Air Canada
Jun 10
KIN3:05 pmKingston Norman Manley
17h 55m
1 stop
ORD9:00 amChicago O'Hare Intl
Jun 14
ORD6:22 pmChicago O'Hare Intl
19h 33m
2 stops
KIN1:55 pmKingston Norman Manley
$505
Air Canada
Jun 10
KIN3:05 pmKingston Norman Manley
27h 47m
2 stops
ORD6:52 pmChicago O'Hare Intl
Jun 14
ORD6:22 pmChicago O'Hare Intl
43h 33m
2 stops
KIN1:55 pmKingston Norman Manley
$516

momondo Fare Finder

 
Customize your flight search to find flights from Kingston to Chicago 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 May 13, 2026.
Use the filters below to find and compare flights from Kingston to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 5/23

12:41 pm-12:24 am

1 stop11h 43m

Chicago O'Hare Intl

Thu 5/28

5:00 am-7:54 pm

1 stop14h 54m

$378

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 5/23

6:21 am-6:11 pm

2 stops11h 50m

Chicago O'Hare Intl

Thu 5/28

7:00 am-7:54 pm

1 stop12h 54m

$382
Quickest round-trip

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 10/15

4:05 pm-11:44 pm

1 stop7h 39m

Chicago O'Hare Intl

Thu 10/22

7:00 am-12:43 pm

1 stop5h 43m

$433

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sun 5/24

6:21 am-9:29 pm

1 stop15h 08m

Chicago O'Hare Intl

Thu 5/28

6:00 pm-11:41 am

1 stop17h 41m

$488

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sun 6/7

6:22 am-11:30 pm

1 stop17h 08m

Chicago O'Hare Intl

Sat 6/13

6:00 pm-11:40 am

1 stop17h 40m

$499

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 6/10

3:05 pm-9:00 am

1 stop17h 55m

Chicago O'Hare Intl

Sun 6/14

8:20 pm-1:55 pm

1 stop17h 35m

$500

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 6/10

3:05 pm-9:00 am

1 stop17h 55m

Chicago O'Hare Intl

Sun 6/14

6:22 pm-1:55 pm

2 stops19h 33m

$505

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 6/26

12:42 pm-12:19 am

1 stop11h 37m

Chicago O'Hare Intl

Wed 7/22

5:00 am-8:09 pm

1 stop15h 09m

$510

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 6/26

6:22 am-7:59 pm

1 stop13h 37m

Chicago O'Hare Intl

Wed 7/22

9:00 am-8:09 pm

2 stops11h 09m

$514

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 6/10

3:05 pm-6:52 pm

2 stops27h 47m

Chicago O'Hare Intl

Sun 6/14

6:22 pm-1:55 pm

2 stops43h 33m

$516

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 Chicago from

How to get the cheapest flight ticket from Kingston to Chicago

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 month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Kingston, with most prices found around $343. If you’re not able to fly to Chicago in May, then June is your next best option. Flight prices from Kingston to Chicago during June average around $380.

When to book flights from Kingston to Chicago

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

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

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

Fastest flight time

7h 39m

Direct flights

None
The fastest flight from Kingston to Chicago takes 7h 39m
There are no direct flights from Kingston to Chicago. There are no popular flight routes from Kingston to Chicago.
Search flight deals

Frequently asked questions about flying from Kingston to Chicago

  • How far is Kingston Norman Manley to Chicago by plane?

    Kingston Norman Manley and Chicago are 1767.3 mi apart from one another. Typically, this will take 7h 39m by plane in normal conditions.

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Kingston Norman Manley Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Kingston to Chicago

Compare and see reviews for airlines that fly from Kingston to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $415Free CancellationRating
7.1
11,662 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Kingston to Chicago?

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 Chicago from Kingston.

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

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

How can momondo help me find flights from Kingston to Chicago?

Once you have performed a search for Kingston to Chicago 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 Kingston to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Kingston 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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport