$101+ Cheap flights from Illinois to Westchester County
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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HPN
Mar 4 — Mar 111
1 adult, Economy
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Find cheap flights from Illinois to Westchester County 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
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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 Illinois to Westchester County
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Cheapest flights from Illinois to Westchester CountyExplore the most affordable flight options available from Illinois to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.
Explore the most affordable flight options available from Illinois to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.
This American Airlines deal was found by Cheapflights users on 2/1. 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 3/119:37 am
STL
- HPN
1 stop6h 10m
American Airlines
Wed 3/185:30 pm
HPN
- STL
1 stop4h 51m
American Airlines
Deal found 2/1![American Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 1/30. 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 3/116:00 am
STL
- HPN
1 stop7h 29m
Delta
Wed 3/1812:48 pm
HPN
- STL
1 stop6h 05m
Delta
Deal found 1/30![Delta logo]()
$279
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/143:03 pm
BMI
- HPN
1 stop5h 56m
American Airlines
Mon 2/165:29 pm
HPN
- BMI
1 stop5h 12m
American Airlines
Deal found 2/1![American Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 8/205:52 pm
STL
- HPN
1 stop4h 32m
American Airlines
Tue 8/2511:00 am
HPN
- STL
1 stop6h 14m
American Airlines
Deal found 2/1![American Airlines logo]()
$298
This Delta deal was found by Cheapflights users on 1/31. 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 3/66:35 am
STL
- HPN
1 stop4h 21m
Delta
Mon 3/96:00 am
HPN
- STL
1 stop6h 09m
Delta
Deal found 1/31![Delta logo]()
$337
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Fri 5/85:46 am
STL
- HPN
1 stop4h 41m
American Airlines
Sun 5/107:00 am
HPN
- STL
1 stop5h 45m
American Airlines
Deal found 2/1![American Airlines logo]()
$347
This American Airlines deal was found by Cheapflights users on 1/31. 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 3/251:38 pm
ORD
- HPN
Nonstop2h 09m
American Airlines
Sat 3/285:29 pm
HPN
- ORD
Nonstop2h 48m
American Airlines
Deal found 1/31![American Airlines logo]()
$355
This Delta deal was found by Cheapflights users on 2/1. 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 8/811:00 am
MLI
- HPN
1 stop6h 12m
Delta
Mon 8/106:00 am
HPN
- MLI
1 stop5h 26m
Delta
Deal found 2/1![Delta logo]()
$355
This Delta deal was found by Cheapflights users on 1/31. 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 5/298:53 am
STL
- HPN
1 stop6h 43m
Delta
Tue 6/26:40 pm
HPN
- STL
1 stop6h 19m
Delta
Deal found 1/31![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 1/31. 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 2/146:35 am
STL
- HPN
1 stop4h 21m
Delta
Sat 2/2112:36 pm
HPN
- STL
1 stop5h 06m
Delta
Deal found 1/31![Delta logo]()
$360
This Delta deal was found by Cheapflights users on 2/1. 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 3/56:00 am
BMI
- HPN
1 stop5h 06m
Delta
Mon 3/96:00 am
HPN
- BMI
1 stop6h 19m
Delta
Deal found 2/1![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 1/31. 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 3/258:55 am
ORD
- HPN
1 stop6h 42m
Delta
Sat 3/283:13 pm
HPN
- ORD
1 stop5h 36m
Delta
Deal found 1/31![Delta logo]()
$375
Best flights from Illinois to Westchester CountyDiscover carefully curated flight deals from Illinois to Westchester County that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 2, 2026.
Discover carefully curated flight deals from Illinois to Westchester County that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 2, 2026.
This American Airlines deal was found by Cheapflights users on 2/1. 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 3/119:37 am
STL
- HPN
1 stop6h 10m
American Airlines
Wed 3/185:30 pm
HPN
- STL
1 stop4h 51m
American Airlines
Deal found 2/1![American Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 1/30. 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 3/116:00 am
STL
- HPN
1 stop7h 29m
Delta
Wed 3/1812:48 pm
HPN
- STL
1 stop6h 05m
Delta
Deal found 1/30![Delta logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Fri 5/86:57 am
ORD
- HPN
2 stops9h 32m
Multiple Airlines
Sun 5/108:00 am
HPN
- ORD
1 stop16h 16m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$377
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/143:03 pm
BMI
- HPN
1 stop5h 56m
American Airlines
Mon 2/165:29 pm
HPN
- BMI
1 stop5h 12m
American Airlines
Deal found 2/1![American Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 7/305:56 pm
STL
- HPN
1 stop4h 32m
American Airlines
Tue 8/46:30 am
HPN
- STL
1 stop4h 31m
American Airlines
Deal found 2/1![American Airlines logo]()
$298
This Delta deal was found by Cheapflights users on 1/31. 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 3/66:35 am
STL
- HPN
1 stop4h 21m
Delta
Mon 3/96:00 am
HPN
- STL
1 stop6h 09m
Delta
Deal found 1/31![Delta logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Thu 3/2612:34 pm
ORD
- HPN
1 stop21h 54m
Multiple Airlines
Mon 3/301:10 pm
HPN
- ORD
2 stops12h 12m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 2/1. 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 5/291:27 pm
STL
- HPN
1 stop7h 53m
Delta
Tue 6/212:45 pm
HPN
- STL
1 stop6h 01m
Delta
Deal found 2/1![Delta logo]()
$359
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Fri 5/85:46 am
STL
- HPN
1 stop4h 41m
American Airlines
Sun 5/107:00 am
HPN
- STL
1 stop5h 45m
American Airlines
Deal found 2/1![American Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 1/31. 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 2/146:35 am
STL
- HPN
1 stop4h 21m
Delta
Sat 2/2112:36 pm
HPN
- STL
1 stop5h 06m
Delta
Deal found 1/31![Delta logo]()
$360
This American Airlines deal was found by Cheapflights users on 1/31. 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 3/251:38 pm
ORD
- HPN
Nonstop2h 09m
American Airlines
Sat 3/285:29 pm
HPN
- ORD
Nonstop2h 48m
American Airlines
Deal found 1/31![American Airlines logo]()
$355
This Delta deal was found by Cheapflights users on 2/1. 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 3/56:00 am
BMI
- HPN
1 stop5h 06m
Delta
Mon 3/96:00 am
HPN
- BMI
1 stop6h 19m
Delta
Deal found 2/1![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 1/31. 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 3/258:55 am
ORD
- HPN
1 stop6h 42m
Delta
Sat 3/283:13 pm
HPN
- ORD
1 stop5h 36m
Delta
Deal found 1/31![Delta logo]()
$375
This American Airlines deal was found by Cheapflights users on 1/30. 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.
Tue 3/175:15 am
PIA
- HPN
1 stop5h 14m
American Airlines
Sun 3/226:30 am
HPN
- PIA
1 stop7h 17m
American Airlines
Deal found 1/30![American Airlines logo]()
$375
This Delta deal was found by Cheapflights users on 2/1. 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 6/109:30 am
MDW
- HPN
1 stop6h 03m
Delta
Tue 6/1612:45 pm
HPN
- MDW
1 stop6h 46m
Delta
Deal found 2/1![Delta logo]()
$375
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Fri 2/1311:31 am
BMI
- HPN
1 stop4h 28m
American Airlines
Mon 2/165:29 pm
HPN
- BMI
1 stop5h 12m
American Airlines
Deal found 2/1![American Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 3/266:38 pm
ORD
- HPN
Nonstop2h 21m
American Airlines
Tue 3/316:30 am
HPN
- ORD
Nonstop2h 50m
American Airlines
Deal found 2/1![American Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 1/31. 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 3/296:00 am
STL
- HPN
1 stop5h 03m
Delta
Sun 4/55:17 pm
HPN
- STL
1 stop4h 25m
Delta
Deal found 1/31![Delta logo]()
$398
This American Airlines deal was found by Cheapflights users on 2/1. 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 4/256:05 am
ORD
- HPN
1 stop5h 55m
American Airlines
Sun 4/265:59 pm
HPN
- ORD
Nonstop2h 55m
American Airlines
Deal found 2/1![American Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 1/31. 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 2/146:00 am
STL
- HPN
1 stop5h 06m
Delta
Sun 2/2212:36 pm
HPN
- STL
1 stop5h 06m
Delta
Deal found 1/31![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 2/1. 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 6/107:10 am
ORD
- HPN
1 stop3h 34m
Delta
Tue 6/164:19 pm
HPN
- ORD
1 stop5h 57m
Delta
Deal found 2/1![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 2/1. 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 2/276:00 am
EVV
- HPN
1 stop5h 06m
Delta
Sun 3/16:40 pm
HPN
- EVV
1 stop4h 40m
Delta
Deal found 2/1![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 2/1. 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 4/255:10 am
ORD
- HPN
1 stop5h 52m
Delta
Sun 4/2612:30 pm
HPN
- ORD
1 stop7h 22m
Delta
Deal found 2/1![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 2/1. 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 4/256:00 am
MDW
- HPN
1 stop7h 29m
Delta
Sun 4/266:00 am
HPN
- MDW
1 stop7h 07m
Delta
Deal found 2/1![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 2/1. 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.
Tue 3/319:35 am
MDW
- HPN
1 stop5h 14m
Delta
Sun 4/512:35 pm
HPN
- MDW
1 stop6h 19m
Delta
Deal found 2/1![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 1/31. 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 2/156:00 am
STL
- HPN
1 stop5h 06m
Delta
Thu 2/1910:28 am
HPN
- STL
1 stop5h 19m
Delta
Deal found 1/31![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 1/31. 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 3/169:35 am
MDW
- HPN
1 stop5h 14m
Delta
Mon 3/2312:35 pm
HPN
- MDW
1 stop6h 19m
Delta
Deal found 1/31![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 2/1. 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 4/246:00 am
MDW
- HPN
1 stop5h 02m
Delta
Sun 4/2612:30 pm
HPN
- MDW
1 stop6h 28m
Delta
Deal found 2/1![Delta logo]()
$443
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Fri 2/274:22 pm
EVV
- HPN
1 stop4h 37m
American Airlines
Sun 3/13:00 pm
HPN
- EVV
2 stops9h 46m
American Airlines
Deal found 2/1![American Airlines logo]()
$892
This Delta deal was found by Cheapflights users on 1/31. 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 2/196:00 am
EVV
- HPN
1 stop5h 06m
Delta
Sun 2/224:29 pm
HPN
- EVV
1 stop6h 51m
Delta
Deal found 1/31![Delta logo]()
$447
Last-minute flights from Illinois to Westchester CountyDiscover last-minute flight deals from Illinois to Westchester County. Data last updated February 2, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Westchester County. Data last updated February 2, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 1/30. 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.
Sun 2/18:18 am
ORD
- HPN
Nonstop2h 10m
American Airlines
Wed 2/185:29 pm
HPN
- ORD
Nonstop2h 48m
American Airlines
Deal found 1/30![American Airlines logo]()
$449
This Delta deal was found by Cheapflights users on 1/30. 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 2/16:50 am
ORD
- HPN
1 stop4h 08m
Delta
Wed 2/183:15 pm
HPN
- ORD
1 stop7h 15m
Delta
Deal found 1/30![Delta logo]()
$469
This Delta deal was found by Cheapflights users on 2/1. 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 2/26:00 am
STL
- HPN
1 stop5h 06m
Delta
Mon 2/95:12 pm
HPN
- STL
1 stop4h 31m
Delta
Deal found 2/1![Delta logo]()
$439
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Fri 2/1311:31 am
BMI
- HPN
1 stop4h 28m
American Airlines
Mon 2/165:29 pm
HPN
- BMI
1 stop5h 12m
American Airlines
Deal found 2/1![American Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/143:03 pm
BMI
- HPN
1 stop5h 56m
American Airlines
Mon 2/165:29 pm
HPN
- BMI
1 stop5h 12m
American Airlines
Deal found 2/1![American Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 1/31. 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 2/146:35 am
STL
- HPN
1 stop4h 21m
Delta
Sat 2/2112:36 pm
HPN
- STL
1 stop5h 06m
Delta
Deal found 1/31![Delta logo]()
$360
This Delta deal was found by Cheapflights users on 1/31. 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 2/146:00 am
STL
- HPN
1 stop5h 06m
Delta
Sun 2/2212:36 pm
HPN
- STL
1 stop5h 06m
Delta
Deal found 1/31![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 1/31. 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 2/156:00 am
STL
- HPN
1 stop5h 06m
Delta
Thu 2/1910:28 am
HPN
- STL
1 stop5h 19m
Delta
Deal found 1/31![Delta logo]()
$417
This American Airlines deal was found by Cheapflights users on 2/2. 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.
Tue 2/176:38 pm
ORD
- HPN
Nonstop2h 21m
American Airlines
Sat 2/214:30 pm
HPN
- ORD
Nonstop2h 48m
American Airlines
Deal found 2/2![American Airlines logo]()
$415
This Delta deal was found by Cheapflights users on 2/2. 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.
Tue 2/1710:35 am
ORD
- HPN
1 stop4h 14m
Delta
Sat 2/2112:56 pm
HPN
- ORD
1 stop7h 23m
Delta
Deal found 2/2![Delta logo]()
$435
This Delta deal was found by Cheapflights users on 1/31. 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 2/206:00 am
EVV
- HPN
1 stop5h 06m
Delta
Sun 2/224:29 pm
HPN
- EVV
1 stop6h 51m
Delta
Deal found 1/31![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 2/1. 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 2/276:00 am
EVV
- HPN
1 stop5h 06m
Delta
Sun 3/16:40 pm
HPN
- EVV
1 stop4h 40m
Delta
Deal found 2/1![Delta logo]()
$407
One-way flights from Illinois to Westchester CountySearch for one-way flight options from Illinois to Westchester County. Find affordable one-way fares based on user searches. Data last updated February 2, 2026.
Search for one-way flight options from Illinois to Westchester County. Find affordable one-way fares based on user searches. Data last updated February 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Tue 3/38:42 pm
ORD
- HPN
2 stops15h 05m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 2/258:30 am
ORD
- HPN
2 stops25h 58m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$108
This Trip.com deal was found by Cheapflights users on 2/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/317:17 am
ORD
- HPN
1 stop13h 34m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Tue 3/319:30 am
MDW
- HPN
2 stops26h 17m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/910:48 am
ORD
- HPN
2 stops23h 40m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Thu 2/264:42 pm
ORD
- HPN
2 stops17h 46m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Thu 2/126:25 am
MDW
- HPN
2 stops28h 03m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 3/23:50 pm
ORD
- HPN
2 stops18h 38m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Tue 4/289:04 am
ORD
- HPN
2 stops26h 43m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/239:22 pm
MDW
- HPN
2 stops38h 25m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sun 2/85:42 pm
STL
- HPN
2 stops16h 46m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$142
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 5/75:46 am
STL
- HPN
1 stop4h 41m
American Airlines
Deal found 2/1![American Airlines logo]()
$159
Find flight deals from Illinois to Westchester County
Keep the following information in mind while searching for Illinois to Westchester County flight deals. Data was last updated February 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $278 (American Airlines) |
One-way from | $101 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $177 |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to Westchester County 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 February 2, 2026.
Use the filters below to find and compare flights from Illinois to Westchester County that are best for you.
Fly from
Illinois
Fly to
Westchester County
Route
Depart
Return
Price
St. LouisWhite Plains
STL - HPN
STLHPN
Lambert-St Louis
Wed 3/11
9:37 am-4:47 pm
1 stop6h 10m
White Plains Westchester County
Wed 3/18
5:30 pm-9:21 pm
1 stop4h 51m
$278
St. LouisWhite Plains
STL - HPN
STLHPN
Lambert-St Louis
Wed 3/11
6:00 am-2:29 pm
1 stop7h 29m
White Plains Westchester County
Wed 3/18
12:48 pm-5:53 pm
1 stop6h 05m
$279
BloomingtonWhite Plains
BMI - HPN
BMIHPN
Bloomington-Normal
Sat 2/14
3:03 pm-9:59 pm
1 stop5h 56m
White Plains Westchester County
Mon 2/16
5:29 pm-9:41 pm
1 stop5h 12m
$291
St. LouisWhite Plains
STL - HPN
STLHPN
Lambert-St Louis
Thu 7/30
5:56 pm-11:28 pm
1 stop4h 32m
White Plains Westchester County
Tue 8/4
6:30 am-10:01 am
1 stop4h 31m
$298
St. LouisWhite Plains
STL - HPN
STLHPN
Lambert-St Louis
Fri 3/6
6:35 am-11:56 am
1 stop4h 21m
White Plains Westchester County
Mon 3/9
6:00 am-11:09 am
1 stop6h 09m
$337
St. LouisWhite Plains
STL - HPN
STLHPN
Lambert-St Louis
Fri 5/8
5:46 am-11:27 am
1 stop4h 41m
White Plains Westchester County
Sun 5/10
7:00 am-11:45 am
1 stop5h 45m
$347
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Wed 3/25
1:38 pm-4:47 pm
Nonstop2h 09m
White Plains Westchester County
Sat 3/28
5:29 pm-7:17 pm
Nonstop2h 48m
$355
St. LouisWhite Plains
STL - HPN
STLHPN
Lambert-St Louis
Fri 5/29
1:27 pm-10:20 pm
1 stop7h 53m
White Plains Westchester County
Tue 6/2
12:45 pm-5:46 pm
1 stop6h 01m
$359
St. LouisWhite Plains
STL - HPN
STLHPN
Lambert-St Louis
Sat 2/14
6:35 am-11:56 am
1 stop4h 21m
White Plains Westchester County
Sat 2/21
12:36 pm-4:42 pm
1 stop5h 06m
$360
BloomingtonWhite Plains
BMI - HPN
BMIHPN
Bloomington-Normal
Thu 3/5
6:00 am-12:06 pm
1 stop5h 06m
White Plains Westchester County
Mon 3/9
6:00 am-11:19 am
1 stop6h 19m
$374
Showing 1-10 of 54 results
Best time to book a flight from Illinois to Westchester County
Have a flexible travel schedule? Discover the best time to fly to Westchester County from Illinois with our price prediction graph.
ORD-HPN
MDW-HPN
STL-HPN
BMI-HPN
EVV-HPN
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 Illinois to Westchester County
USIL-zzREU
ORD-HPN
MDW-HPN
STL-HPN
BMI-HPN
What is the cheapest month to book a flight from Illinois to Westchester County?
Currently, March is the cheapest month in which you can book a flight from Illinois to Westchester County (average of $135). Flying from Illinois to Westchester County in November is currently the most expensive (average of $416). 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.
What is the cheapest time of day to fly from IL to REU?
Find hourly flight availability from Illinois to Westchester County. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 2, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 4% on flights from Illinois to Westchester County by exploring options for tickets in the morning.
What is the cheapest day to fly from Illinois to Westchester County?
Use this chart to determine the cheapest time to fly round-trip from Illinois to Westchester County. Price data was last updated on January 24, 2026.
Travelers seeking maximum savings on their Illinois to Westchester County flight should consider departing on Sunday at noon when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Illinois to Westchester County
Explore weekly flight availability from Illinois to Westchester County. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 2, 2026.
The most flights from USIL to zzREU are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).
Related info for your journey
Find useful and relevant information for your journey from Illinois to Westchester County. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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 for Illinois to Westchester County
See prices for flight routes from nearby airports that may be better suited for you.
Top airline flying from Illinois to Westchester County
Discover the top airline that operate flights from Illinois to Westchester County. 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 February 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$375 | Average$480 | FlexibilityNo cancel fee | On-time71% |