$173+ Cheap flights from Chicago (CHI) to Kingston (KIN)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KIN
Sep 7 — Sep 141
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Kingston with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Kingston
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to KingstonExplore the most affordable flight options available from Chicago to Kingston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 8, 2026.
Explore the most affordable flight options available from Chicago to Kingston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 8, 2026.
This Orbitz deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/13:45 pm -
2 stops42h 50m
Wed 11/1112:45 pm -
1 stop29h 58m
Deal found 8/7![Air Canada logo]()
$461
This Orbitz deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:40 am -
2 stops29h 15m
Thu 9/31:55 pm -
1 stop9h 49m
Deal found 8/7![Multiple Airlines logo]()
$465
This Air Canada deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:58 pm -
2 stops40h 37m
Thu 11/1212:45 pm -
1 stop29h 58m
Deal found 8/5![Air Canada logo]()
$485
This Cheapflightsfares deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:00 am -
1 stop6h 45m
Sat 10/1010:10 am -
1 stop11h 46m
Deal found 8/6![JetBlue logo]()
$491
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:37 am -
2 stops23h 58m
Thu 11/1212:45 pm -
1 stop27h 53m
Deal found 8/7![Air Canada logo]()
$503
This FlightHub deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:25 am -
1 stop27h 00m
Sat 9/52:15 am -
1 stop14h 01m
Deal found 8/4![Multiple Airlines logo]()
$511
This Orbitz deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:00 am -
1 stop5h 45m
Wed 11/1112:45 pm -
1 stop27h 53m
Deal found 8/7![Multiple Airlines logo]()
$515
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:05 am -
1 stop14h 05m
Sat 9/269:10 am -
1 stop13h 34m
Deal found 8/5![Delta logo]()
$556
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:29 am -
2 stops10h 41m
Mon 9/219:10 am -
1 stop13h 34m
Deal found 8/4![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:54 am -
1 stop9h 19m
Wed 9/99:10 am -
1 stop13h 34m
Deal found 8/5![Delta logo]()
$675
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/79:29 am -
2 stops10h 46m
Sat 10/179:15 am -
2 stops8h 45m
Deal found 8/5![Delta logo]()
$680
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:05 am -
1 stop14h 08m
Sat 8/229:13 am -
1 stop13h 23m
Deal found 8/4![Delta logo]()
$698
Best flights from Chicago to KingstonDiscover carefully curated flight deals from Chicago to Kingston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 8, 2026.
Discover carefully curated flight deals from Chicago to Kingston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 8, 2026.
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/910:57 am -
2 stops47h 38m
Thu 11/1212:45 pm -
2 stops54h 35m
Deal found 8/7![Air Canada logo]()
$499
This Copa Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:20 pm -
1 stop22h 38m
Sat 10/102:57 pm -
1 stop10h 00m
Deal found 8/5![Copa Airlines logo]()
$516
This JetBlue deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:00 am -
1 stop5h 45m
Thu 11/124:55 pm -
1 stop7h 49m
Deal found 8/7![JetBlue logo]()
$532
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:05 am -
1 stop14h 05m
Mon 9/289:10 am -
1 stop7h 05m
Deal found 8/3![Delta logo]()
$556
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/205:30 am -
2 stops32h 21m
Sun 9/272:57 pm -
1 stop10h 05m
Deal found 8/6![United Airlines logo]()
$796
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:05 am -
1 stop12h 05m
Mon 9/149:10 am -
1 stop11h 46m
Deal found 8/3![Delta logo]()
$556
This KAYAK deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:35 am -
1 stop29h 17m
Fri 11/132:58 pm -
1 stop22h 48m
Deal found 8/4![Copa Airlines logo]()
$566
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:27 am -
1 stop14h 48m
Sat 10/179:15 am -
1 stop7h 48m
Deal found 8/4![Delta logo]()
$556
This JetBlue deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:00 am -
1 stop10h 18m
Sat 8/291:55 pm -
1 stop9h 49m
Deal found 8/6![JetBlue logo]()
$675
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:29 am -
2 stops10h 41m
Sat 9/269:10 am -
2 stops9h 12m
Deal found 8/5![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/41:05 pm -
1 stop5h 55m
Fri 1/159:00 am -
2 stops10h 37m
Deal found 8/3![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:29 am -
2 stops10h 41m
Mon 9/219:10 am -
1 stop13h 34m
Deal found 8/4![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:04 am -
1 stop14h 11m
Sat 10/179:15 am -
2 stops8h 45m
Deal found 8/4![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:29 am -
2 stops10h 41m
Wed 9/239:10 am -
2 stops9h 23m
Deal found 8/4![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:05 am -
2 stops13h 05m
Wed 9/239:10 am -
2 stops11h 20m
Deal found 8/4![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1311:28 am -
1 stop6h 32m
Thu 1/219:00 am -
1 stop14h 10m
Deal found 8/4![Delta logo]()
$765
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:05 am -
1 stop14h 05m
Sat 10/109:15 am -
1 stop13h 18m
Deal found 8/7![Delta logo]()
$804
Last-minute flights from Chicago to KingstonDiscover last-minute flight deals from Chicago to Kingston. Data last updated August 8, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kingston. Data last updated August 8, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:05 am -
1 stop14h 08m
Sat 8/229:13 am -
1 stop13h 23m
Deal found 8/4![Delta logo]()
$698
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:05 am -
1 stop14h 08m
Wed 9/29:13 am -
1 stop13h 23m
Deal found 8/4![Delta logo]()
$694
This Orbitz deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:40 am -
2 stops29h 15m
Thu 9/31:55 pm -
1 stop9h 49m
Deal found 8/7![Multiple Airlines logo]()
$465
This Orbitz deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:40 am -
2 stops25h 45m
Sat 9/52:15 am -
1 stop14h 01m
Deal found 8/4![Multiple Airlines logo]()
$485
This Priceline deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:40 am -
2 stops23h 45m
Wed 9/93:05 pm -
1 stop8h 03m
Deal found 8/5![Multiple Airlines logo]()
$524
This Air Canada deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:40 am -
2 stops23h 45m
Wed 9/93:05 pm -
2 stops19h 10m
Deal found 8/5![Air Canada logo]()
$529
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:54 am -
1 stop9h 19m
Wed 9/99:10 am -
1 stop13h 34m
Deal found 8/5![Delta logo]()
$675
This Copa Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:20 pm -
1 stop22h 31m
Mon 9/142:57 pm -
1 stop10h 05m
Deal found 8/5![Copa Airlines logo]()
$531
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:40 pm -
1 stop13h 45m
Mon 9/143:05 pm -
1 stop17h 55m
Deal found 8/7![Air Canada logo]()
$539
This Copa Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/163:20 pm -
1 stop22h 31m
Wed 9/232:57 pm -
1 stop10h 05m
Deal found 8/4![Copa Airlines logo]()
$516
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1911:35 am -
1 stop8h 35m
Mon 9/219:10 am -
1 stop13h 34m
Deal found 8/4![Delta logo]()
$556
This Priceline deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:00 am -
1 stop6h 45m
Mon 9/283:05 pm -
1 stop16h 55m
Deal found 8/3![Multiple Airlines logo]()
$544
One-way flights from Chicago to KingstonSearch for one-way flight options from Chicago to Kingston. Find affordable one-way fares based on user searches. Data last updated August 8, 2026.
Search for one-way flight options from Chicago to Kingston. Find affordable one-way fares based on user searches. Data last updated August 8, 2026.
This Orbitz deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:40 am -
2 stops49h 45m
Deal found 8/7![Air Canada logo]()
$173
This Travelocity deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:40 am -
2 stops25h 45m
Deal found 8/3![Air Canada logo]()
$185
This Travelocity deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:35 pm -
1 stop20h 20m
Deal found 8/6![Air Canada logo]()
$228
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:42 am -
1 stop7h 20m
Deal found 8/5![American Airlines logo]()
$229
This KAYAK deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:00 am -
1 stop5h 45m
Deal found 8/5![JetBlue logo]()
$231
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:05 am -
1 stop14h 05m
Deal found 8/5![Delta logo]()
$233
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:40 am -
1 stop13h 30m
Deal found 8/3![Delta logo]()
$233
This American Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:37 am -
1 stop7h 49m
Deal found 8/3![American Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:54 pm -
3 stops43h 16m
Deal found 8/3![Multiple Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2210:56 am -
1 stop9h 17m
Deal found 8/7![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:42 pm -
2 stops25h 31m
Deal found 8/7![Delta logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:05 am -
3 stops12h 40m
Deal found 8/5![Multiple Airlines logo]()
$406
Find flight deals from Chicago to Kingston
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Kingston (KIN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $461 (Orbitz) |
One-way from | $173 (Orbitz) |
Popular in | November |
Cheapest in | October |
Average price | $513 |
Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated August 8, 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
Cheapest round-trip
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Mon 11/9
10:57 am-11:35 am
2 stops47h 38m
Kingston Norman Manley
Thu 11/12
12:45 pm-6:20 pm
2 stops54h 35m
$499
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Sat 10/3
3:20 pm-1:58 pm
1 stop22h 38m
Kingston Norman Manley
Sat 10/10
2:57 pm-12:57 am
1 stop10h 00m
$516
Quickest round-trip
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Mon 11/9
7:00 am-1:45 pm
1 stop5h 45m
Kingston Norman Manley
Thu 11/12
4:55 pm-11:44 pm
1 stop7h 49m
$532
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Fri 9/25
6:05 am-8:10 pm
1 stop14h 05m
Kingston Norman Manley
Mon 9/28
9:10 am-4:15 pm
1 stop7h 05m
$556
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Wed 9/9
8:05 am-8:10 pm
1 stop12h 05m
Kingston Norman Manley
Mon 9/14
9:10 am-8:56 pm
1 stop11h 46m
$556
ChicagoKingston
ORD Chicago O'Hare Intl - KIN Kingston Norman Manley
ORDKIN
Chicago O'Hare Intl
Wed 10/7
5:27 am-8:15 pm
1 stop14h 48m
Kingston Norman Manley
Sat 10/17
9:15 am-5:03 pm
1 stop7h 48m
$556
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Sat 9/19
9:29 am-8:10 pm
2 stops10h 41m
Kingston Norman Manley
Sat 9/26
9:10 am-6:22 pm
2 stops9h 12m
$561
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Mon 1/4
1:05 pm-8:00 pm
1 stop5h 55m
Kingston Norman Manley
Fri 1/15
9:00 am-6:37 pm
2 stops10h 37m
$561
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Sat 9/19
9:29 am-8:10 pm
2 stops10h 41m
Kingston Norman Manley
Mon 9/21
9:10 am-10:44 pm
1 stop13h 34m
$561
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Wed 10/7
6:04 am-8:15 pm
1 stop14h 11m
Kingston Norman Manley
Sat 10/17
9:15 am-6:00 pm
2 stops8h 45m
$561
Showing 1-10 of 36 resultsSorted by cheapest first
Compare providers for flights from Chicago to Kingston
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Kingston in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Kingston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Kingston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Kingston flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Kingston flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Kingston flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Kingston
Have a flexible travel schedule? Discover the best time to fly to Kingston from Chicago with our price prediction graph.
CHI-KIN
ORD-KIN
MDW-KIN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Kingston
CHI-KIN
ORD-KIN
MDW-KIN
What is the cheapest month to book a flight from Chicago to Kingston?
Currently, August is the cheapest month in which you can book a flight from Chicago to Kingston (average of $508). Flying from Chicago to Kingston in December is currently the most expensive (average of $883). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Chicago to Kingston?
Airfare is below average for this route at the moment.
Chicago to Kingston flights typically cost between $464 and $536 in November.The cheapest round-trip price found within the last 5 days was $461 on Air Canada (Nov 1-Nov 11).
Reviews of airlines servicing Kingston
Get insights into the airlines that provide service to Kingston. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kingston. Reviews last updated August 8, 2026.
Read through reviews of airlines operating flights from Chicago to Kingston, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.2
Overall
7.1
Boarding
7.5
Entertainment
6.8
Food
6.4
Crew
7.9
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Comfort
7.2
Overall
7.1
Boarding
7.5
Entertainment
6.8
Food
6.4
Crew
7.9
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Kingston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Kingston?
Book flights to Kingston if you plan to visit one of these locationsPort Antonio
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Kingston flight routes
Other flight options
Other flights from Chicago
Popular flights
Alternative routes for Chicago to Kingston
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Kingston by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Kingston by cabin class
Find flights from Chicago to Kingston, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Kingston
Explore flights to Kingston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 8, 2026.
Chicago and Kingston flights
Browse other Chicago and Kingston flight options. Last updated on August 8, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Kingston
Discover the top 2 airlines that operate flights from Chicago to Kingston. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$433 | Average$660 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$445 | Average$645 | FlexibilityNo cancel fee | On-timeN/A |