$138+ Cheap flights from Chicago (CHI) to White Plains (HPN)
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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Jun 21 — Jun 281
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to White Plains 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 Chicago to White Plains
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Cheapest flights from Chicago to White PlainsExplore the most affordable flight options available from Chicago to White Plains. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 22, 2026.
Explore the most affordable flight options available from Chicago to White Plains. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 22, 2026.
This American Airlines deal was found by Cheapflights users on 5/21. 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 8/157:29 pm
ORD
- HPN
Nonstop2h 22m
American Airlines
Sat 8/224:30 pm
HPN
- ORD
Nonstop2h 48m
American Airlines
Deal found 5/21![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 5/20. 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 8/116:42 pm
MDW
- HPN
1 stop16h 14m
Delta
Mon 8/315:10 pm
HPN
- MDW
1 stop16h 32m
Delta
Deal found 5/20![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 5/17. 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 6/107:17 pm
ORD
- HPN
1 stop15h 41m
Delta
Tue 6/165:10 pm
HPN
- ORD
1 stop15h 55m
Delta
Deal found 5/17![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 5/20. 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 8/86:51 am
ORD
- HPN
1 stop4h 05m
Delta
Wed 9/212:45 pm
HPN
- ORD
1 stop8h 39m
Delta
Deal found 5/20![Delta logo]()
$410
This Delta deal was found by Cheapflights users on 5/20. 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 8/89:24 am
MDW
- HPN
1 stop5h 24m
Delta
Mon 8/315:10 pm
HPN
- MDW
1 stop16h 32m
Delta
Deal found 5/20![Delta logo]()
$410
This Delta deal was found by Cheapflights users on 5/17. 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 6/107:17 pm
ORD
- HPN
1 stop15h 41m
Delta
Mon 6/155:10 pm
HPN
- ORD
1 stop15h 55m
Delta
Deal found 5/17![Delta logo]()
$413
This Delta deal was found by Cheapflights users on 5/17. 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 8/156:40 am
ORD
- HPN
1 stop6h 49m
Delta
Sat 8/2212:48 pm
HPN
- ORD
1 stop7h 07m
Delta
Deal found 5/17![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 5/20. 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 8/89:24 am
MDW
- HPN
1 stop5h 24m
Delta
Sat 8/296:00 am
HPN
- MDW
1 stop5h 10m
Delta
Deal found 5/20![Delta logo]()
$415
This American Airlines deal was found by Cheapflights users on 5/17. 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 6/107:37 pm
ORD
- HPN
Nonstop2h 22m
American Airlines
Tue 6/1612:00 pm
HPN
- ORD
Nonstop2h 37m
American Airlines
Deal found 5/17![American Airlines logo]()
$425
This Delta deal was found by Cheapflights users on 5/20. 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 8/107:25 pm
ORD
- HPN
1 stop15h 31m
Delta
Tue 9/112:45 pm
HPN
- ORD
1 stop8h 39m
Delta
Deal found 5/20![Delta logo]()
$432
This Delta deal was found by Cheapflights users on 5/20. 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 8/106:42 pm
MDW
- HPN
1 stop16h 14m
Delta
Mon 8/315:10 pm
HPN
- MDW
1 stop16h 32m
Delta
Deal found 5/20![Delta logo]()
$432
This American Airlines deal was found by Cheapflights users on 5/20. 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 5/2911:55 am
ORD
- HPN
1 stop7h 34m
American Airlines
Tue 6/27:10 am
HPN
- ORD
Nonstop2h 43m
American Airlines
Deal found 5/20![American Airlines logo]()
$435
Best flights from Chicago to White PlainsDiscover carefully curated flight deals from Chicago to White Plains that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 22, 2026.
Discover carefully curated flight deals from Chicago to White Plains that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 22, 2026.
This Delta deal was found by Cheapflights users on 5/21. 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 9/27:10 am
ORD
- HPN
1 stop8h 23m
Delta
Mon 9/75:10 pm
HPN
- ORD
1 stop18h 14m
Delta
Deal found 5/21![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 5/20. 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 8/126:51 am
ORD
- HPN
1 stop7h 57m
Delta
Tue 9/15:10 pm
HPN
- ORD
1 stop15h 46m
Delta
Deal found 5/20![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 5/20. 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 8/116:42 pm
MDW
- HPN
1 stop16h 14m
Delta
Sat 8/294:29 pm
HPN
- MDW
1 stop7h 07m
Delta
Deal found 5/20![Delta logo]()
$410
This Delta deal was found by Cheapflights users on 5/20. 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 8/89:24 am
MDW
- HPN
1 stop5h 24m
Delta
Mon 8/315:10 pm
HPN
- MDW
1 stop16h 32m
Delta
Deal found 5/20![Delta logo]()
$410
This Delta deal was found by Cheapflights users on 5/17. 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 8/156:40 am
ORD
- HPN
1 stop6h 49m
Delta
Sat 8/2212:48 pm
HPN
- ORD
1 stop7h 07m
Delta
Deal found 5/17![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 5/18. 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 6/236:00 am
MDW
- HPN
1 stop7h 28m
Delta
Sat 6/2712:38 pm
HPN
- MDW
1 stop5h 27m
Delta
Deal found 5/18![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 5/20. 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 8/107:25 pm
ORD
- HPN
1 stop15h 31m
Delta
Tue 9/112:45 pm
HPN
- ORD
1 stop8h 39m
Delta
Deal found 5/20![Delta logo]()
$432
This Delta deal was found by Cheapflights users on 5/20. 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 8/106:42 pm
MDW
- HPN
1 stop16h 14m
Delta
Mon 8/315:10 pm
HPN
- MDW
1 stop16h 32m
Delta
Deal found 5/20![Delta logo]()
$432
This Delta deal was found by Cheapflights users on 5/20. 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 8/106:42 pm
MDW
- HPN
1 stop16h 14m
Delta
Sat 8/296:00 am
HPN
- MDW
1 stop5h 10m
Delta
Deal found 5/20![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 5/17. 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 6/107:01 am
ORD
- HPN
1 stop3h 57m
Delta
Wed 6/245:10 pm
HPN
- ORD
1 stop4h 21m
Delta
Deal found 5/17![Delta logo]()
$445
This Delta deal was found by Cheapflights users on 5/21. 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 9/311:30 am
ORD
- HPN
1 stop4h 03m
Delta
Wed 9/912:45 pm
HPN
- ORD
1 stop8h 39m
Delta
Deal found 5/21![Delta logo]()
$454
This Delta deal was found by Cheapflights users on 5/20. 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 8/86:51 am
ORD
- HPN
1 stop4h 05m
Delta
Sun 8/306:49 pm
HPN
- ORD
1 stop6h 09m
Delta
Deal found 5/20![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 5/19. 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 8/69:59 am
MDW
- HPN
1 stop5h 38m
Delta
Tue 8/1112:36 pm
HPN
- MDW
1 stop6h 57m
Delta
Deal found 5/19![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 5/19. 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 6/279:17 am
MDW
- HPN
1 stop5h 32m
Delta
Mon 6/294:29 pm
HPN
- MDW
1 stop6h 48m
Delta
Deal found 5/19![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 5/20. 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 8/76:05 am
MDW
- HPN
1 stop4h 58m
Delta
Fri 8/145:17 pm
HPN
- MDW
1 stop17h 00m
Delta
Deal found 5/20![Delta logo]()
$481
This Delta deal was found by Cheapflights users on 5/19. 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 6/279:17 am
MDW
- HPN
1 stop5h 32m
Delta
Wed 7/112:38 pm
HPN
- MDW
1 stop6h 53m
Delta
Deal found 5/19![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 5/19. 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 6/276:00 am
MDW
- HPN
1 stop7h 28m
Delta
Tue 6/304:29 pm
HPN
- MDW
1 stop6h 48m
Delta
Deal found 5/19![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 5/21. 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 7/1011:05 am
MDW
- HPN
1 stop6h 02m
Delta
Tue 7/2112:36 pm
HPN
- MDW
1 stop6h 49m
Delta
Deal found 5/21![Delta logo]()
$489
This Delta deal was found by Cheapflights users on 5/17. 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 7/33:22 pm
ORD
- HPN
1 stop6h 03m
Delta
Mon 7/610:29 am
HPN
- ORD
2 stops9h 00m
Delta
Deal found 5/17![Delta logo]()
$602
This Delta deal was found by Cheapflights users on 5/21. 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 7/235:30 am
ORD
- HPN
1 stop5h 38m
Delta
Mon 7/2712:36 pm
HPN
- ORD
1 stop4h 47m
Delta
Deal found 5/21![Delta logo]()
$603
This Delta deal was found by Cheapflights users on 5/17. 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 7/3111:30 am
ORD
- HPN
2 stops9h 55m
Delta
Wed 8/56:49 pm
HPN
- ORD
1 stop6h 09m
Delta
Deal found 5/17![Delta logo]()
$612
This Delta deal was found by Cheapflights users on 5/21. 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 7/1011:30 am
ORD
- HPN
2 stops9h 55m
Delta
Tue 7/215:12 pm
HPN
- ORD
1 stop4h 19m
Delta
Deal found 5/21![Delta logo]()
$612
Last-minute flights from Chicago to White PlainsDiscover last-minute flight deals from Chicago to White Plains. Data last updated May 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to White Plains. Data last updated May 22, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/21. 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 5/239:22 am
MDW
- HPN
1 stop5h 27m
Delta
Sun 5/244:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Deal found 5/21![Delta logo]()
$445
This American Airlines deal was found by Cheapflights users on 5/20. 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 5/2911:55 am
ORD
- HPN
1 stop7h 34m
American Airlines
Tue 6/27:10 am
HPN
- ORD
Nonstop2h 43m
American Airlines
Deal found 5/20![American Airlines logo]()
$435
This Delta deal was found by Cheapflights users on 5/20. 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 5/295:30 am
ORD
- HPN
1 stop5h 32m
Delta
Sat 6/65:15 pm
HPN
- ORD
1 stop3h 59m
Delta
Deal found 5/20![Delta logo]()
$445
This Delta deal was found by Cheapflights users on 5/17. 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 6/107:17 pm
ORD
- HPN
1 stop15h 41m
Delta
Tue 6/165:10 pm
HPN
- ORD
1 stop15h 55m
Delta
Deal found 5/17![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 5/17. 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 6/107:17 pm
ORD
- HPN
1 stop15h 41m
Delta
Mon 6/155:10 pm
HPN
- ORD
1 stop15h 55m
Delta
Deal found 5/17![Delta logo]()
$413
This American Airlines deal was found by Cheapflights users on 5/17. 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 6/107:37 pm
ORD
- HPN
Nonstop2h 22m
American Airlines
Tue 6/1612:00 pm
HPN
- ORD
Nonstop2h 37m
American Airlines
Deal found 5/17![American Airlines logo]()
$425
This Delta deal was found by Cheapflights users on 5/17. 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 6/107:17 pm
ORD
- HPN
1 stop15h 41m
Delta
Sat 6/1312:38 pm
HPN
- ORD
1 stop4h 52m
Delta
Deal found 5/17![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 5/17. 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 6/136:35 am
ORD
- HPN
1 stop6h 53m
Delta
Tue 6/1612:38 pm
HPN
- ORD
1 stop8h 53m
Delta
Deal found 5/17![Delta logo]()
$440
This American Airlines deal was found by Cheapflights users on 5/21. 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 6/207:29 pm
ORD
- HPN
Nonstop2h 22m
American Airlines
Sat 6/275:46 pm
HPN
- ORD
Nonstop2h 54m
American Airlines
Deal found 5/21![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 5/21. 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 6/206:00 am
MDW
- HPN
1 stop7h 28m
Delta
Sat 6/2712:38 pm
HPN
- MDW
1 stop5h 27m
Delta
Deal found 5/21![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 5/19. 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 6/273:25 pm
ORD
- HPN
1 stop6h 00m
Delta
Thu 7/25:10 pm
HPN
- ORD
1 stop4h 21m
Delta
Deal found 5/19![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 5/19. 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 6/279:17 am
MDW
- HPN
1 stop5h 32m
Delta
Mon 6/294:29 pm
HPN
- MDW
1 stop6h 48m
Delta
Deal found 5/19![Delta logo]()
$459
One-way flights from Chicago to White PlainsSearch for one-way flight options from Chicago to White Plains. Find affordable one-way fares based on user searches. Data last updated May 22, 2026.
Search for one-way flight options from Chicago to White Plains. Find affordable one-way fares based on user searches. Data last updated May 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 8/181:50 pm
ORD
- HPN
2 stops20h 30m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 8/121:50 pm
ORD
- HPN
2 stops30h 10m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 7/76:00 am
MDW
- HPN
2 stops28h 20m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 8/191:50 pm
ORD
- HPN
2 stops30h 10m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 7/151:50 pm
ORD
- HPN
2 stops30h 10m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/106:55 am
ORD
- HPN
2 stops37h 05m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 8/148:05 am
ORD
- HPN
3 stops26h 15m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 7/312:04 pm
MDW
- HPN
2 stops22h 16m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/161:29 pm
ORD
- HPN
3 stops44h 58m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 8/131:50 pm
ORD
- HPN
2 stops26h 39m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/174:59 pm
ORD
- HPN
2 stops17h 28m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 8/1012:44 am
ORD
- HPN
3 stops33h 36m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$181
Find flight deals from Chicago to White Plains
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to White Plains (HPN). 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 May 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $395 (American Airlines) |
One-way from | $138 (Kiwi.com) |
Popular in | May |
Cheapest in | July |
Average price | $523 |
Good round-trip deal | $439 or less |
Good one-way deal | $285 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to White Plains 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 May 22, 2026.
Use the filters below to find and compare flights from Chicago to White Plains that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Wed 9/2
7:10 am-4:33 pm
1 stop8h 23m
White Plains Westchester County
Mon 9/7
5:10 pm-10:24 am
1 stop18h 14m
$405
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Wed 8/12
6:51 am-3:48 pm
1 stop7h 57m
White Plains Westchester County
Tue 9/1
5:10 pm-7:56 am
1 stop15h 46m
$405
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Tue 8/11
6:42 pm-11:56 am
1 stop16h 14m
White Plains Westchester County
Sat 8/29
4:29 pm-10:36 pm
1 stop7h 07m
$410
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Sat 8/8
9:24 am-3:48 pm
1 stop5h 24m
White Plains Westchester County
Mon 8/31
5:10 pm-8:42 am
1 stop16h 32m
$410
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Sat 8/15
6:40 am-2:29 pm
1 stop6h 49m
White Plains Westchester County
Sat 8/22
12:48 pm-6:55 pm
1 stop7h 07m
$415
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Tue 6/23
6:00 am-2:28 pm
1 stop7h 28m
White Plains Westchester County
Sat 6/27
12:38 pm-5:05 pm
1 stop5h 27m
$415
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Mon 8/10
7:25 pm-11:56 am
1 stop15h 31m
White Plains Westchester County
Tue 9/1
12:45 pm-8:24 pm
1 stop8h 39m
$432
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Mon 8/10
6:42 pm-11:56 am
1 stop16h 14m
White Plains Westchester County
Mon 8/31
5:10 pm-8:42 am
1 stop16h 32m
$432
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Mon 8/10
6:42 pm-11:56 am
1 stop16h 14m
White Plains Westchester County
Sat 8/29
6:00 am-10:10 am
1 stop5h 10m
$437
Quickest round-trip
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Wed 6/10
7:01 am-11:58 am
1 stop3h 57m
White Plains Westchester County
Wed 6/24
5:10 pm-8:31 pm
1 stop4h 21m
$445
Showing 1-10 of 46 resultsSorted by cheapest first
Compare providers for flights from Chicago to White Plains
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 White Plains in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-White Plains flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-White Plains flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-White Plains flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-White Plains 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-White Plains 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 White Plains
Have a flexible travel schedule? Discover the best time to fly to White Plains from Chicago with our price prediction graph.
CHI-HPN
ORD-HPN
MDW-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 Chicago to White Plains
CHI-HPN
ORD-HPN
MDW-HPN
What is the cheapest month to book a flight from Chicago to White Plains?
Currently, March is the cheapest month in which you can book a flight from Chicago to White Plains (average of $124). Flying from Chicago to White Plains in February is currently the most expensive (average of $415). 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 CHI to HPN?
Find hourly flight availability from Chicago to White Plains. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 22, 2026.
It’s typically best to fly out from Chicago to White Plains in the morning. Doing so could potentially save you 4% on the flight price compared to flying in the afternoon, which is usually more expensive.
Weekly flight availability from Chicago to White Plains
Explore weekly flight availability from Chicago to White Plains. 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 May 22, 2026.
The most flights from CHI to HPN are scheduled on a Thursday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Chicago to White Plains?
What is the cheapest day to fly from Chicago to White Plains?
Use this chart to determine the cheapest time to fly round-trip from Chicago to White Plains. Price data was last updated on May 16, 2026.
Travelers seeking maximum savings on their Chicago to White Plains flight should consider departing on Saturday afternoons 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.
Reviews of airlines servicing White Plains
Get insights into the airlines that provide service to White Plains. 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 White Plains. Reviews last updated May 22, 2026.
Peruse reviews from past customers who have flown with American Airlines from Chicago to White Plains to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.5
Overall
7.1
Entertainment
6.9
Food
6.4
Comfort
7.2
Crew
7.9
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Boarding
7.5
Overall
7.1
Entertainment
6.9
Food
6.4
Comfort
7.2
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 White Plains. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Chicago and White Plains flights
Browse other Chicago and White Plains flight options. Last updated on May 22, 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 May 22, 2026.
Popular flight searches
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Other flights to White Plains
Explore flights to White Plains departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 22, 2026.
Top airline flying from Chicago to White Plains
Discover the top airline that operate flights from Chicago to White Plains. 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 May 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$380 | Average$486 | FlexibilityNo cancel fee | On-time71% |