$138+ Cheap flights from White Plains (HPN) to Chicago (CHI)
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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Jun 21 — Jun 281
Round-trip
1 adult, Economy
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Find cheap flights from White Plains to Chicago 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.Cheapflights Tip: The best prices from White Plains Westchester County to Chicago are usually found in January or September, booked 72 days in advance, depart on a Saturday or Wednesday and return on a Saturday
Cheap flight deals from White Plains to Chicago
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Best
Last-minute
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Cheapest flights from White Plains to ChicagoExplore the most affordable flight options available from White Plains to Chicago. 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 White Plains to Chicago. 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.
Fri 5/296:30 am
HPN
- ORD
1 stop4h 24m
American Airlines
Wed 6/37:37 pm
ORD
- HPN
Nonstop2h 21m
American Airlines
Deal found 5/21![American Airlines logo]()
$435
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.
Thu 6/256:19 am
HPN
- ORD
Nonstop2h 41m
American Airlines
Sat 6/276:21 pm
ORD
- HPN
Nonstop2h 28m
American Airlines
Deal found 5/20![American Airlines logo]()
$439
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:39 pm
HPN
- ORD
Nonstop2h 50m
American Airlines
Fri 7/107:39 pm
ORD
- HPN
Nonstop2h 20m
American Airlines
Deal found 5/19![American Airlines logo]()
$441
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 5/234:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Wed 5/2710:59 am
MDW
- HPN
1 stop6h 01m
Delta
Deal found 5/21![Delta logo]()
$445
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.
Thu 5/2810:29 am
HPN
- ORD
1 stop7h 27m
Delta
Sat 6/611:09 am
ORD
- HPN
1 stop3h 40m
Delta
Deal found 5/20![Delta logo]()
$445
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:29 pm
HPN
- ORD
1 stop18h 10m
JetBlue
Wed 7/152:35 pm
ORD
- HPN
1 stop7h 24m
JetBlue
Deal found 5/18![JetBlue logo]()
$448
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 7/145:12 pm
HPN
- ORD
1 stop15h 47m
Delta
Sun 7/195:30 am
ORD
- HPN
1 stop5h 38m
Delta
Deal found 5/18![Delta logo]()
$454
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/137:24 am
HPN
- ORD
Nonstop2h 41m
American Airlines
Tue 6/168:10 am
ORD
- HPN
Nonstop2h 19m
American Airlines
Deal found 5/19![American Airlines logo]()
$455
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:30 pm
HPN
- ORD
2 stops11h 14m
JetBlue
Tue 9/82:35 pm
ORD
- HPN
1 stop7h 10m
JetBlue
Deal found 5/21![JetBlue logo]()
$458
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.
Thu 7/912:36 pm
HPN
- MDW
1 stop6h 49m
Delta
Tue 7/216:00 am
MDW
- HPN
1 stop7h 29m
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 6/256:29 am
HPN
- ORD
1 stop7h 07m
Delta
Sat 6/275:30 am
ORD
- HPN
1 stop7h 58m
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.
Sat 5/234:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Sat 5/309:22 am
MDW
- HPN
1 stop5h 27m
Delta
Deal found 5/20![Delta logo]()
$475
Best flights from White Plains to ChicagoDiscover carefully curated flight deals from White Plains to Chicago 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 White Plains to Chicago 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 5/17. 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 7/294:29 pm
HPN
- MDW
1 stop6h 46m
Delta
Sun 8/29:19 am
MDW
- HPN
1 stop5h 28m
Delta
Deal found 5/17![Delta logo]()
$487
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.
Thu 7/236:00 am
HPN
- ORD
1 stop5h 10m
Delta
Tue 7/288:03 am
ORD
- HPN
1 stop5h 26m
Delta
Deal found 5/18![Delta logo]()
$487
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.
Fri 7/244:29 pm
HPN
- MDW
1 stop6h 46m
Delta
Sun 7/266:00 am
MDW
- HPN
1 stop5h 08m
Delta
Deal found 5/18![Delta logo]()
$503
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.
Fri 9/254:19 pm
HPN
- MDW
1 stop6h 27m
Delta
Sun 9/276:00 am
MDW
- HPN
1 stop5h 13m
Delta
Deal found 5/18![Delta logo]()
$503
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 9/113:15 pm
HPN
- ORD
1 stop7h 19m
Delta
Sun 9/135:30 am
ORD
- HPN
1 stop5h 43m
Delta
Deal found 5/21![Delta logo]()
$503
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 7/3112:36 pm
HPN
- ORD
1 stop4h 47m
Delta
Sun 8/25:30 am
ORD
- HPN
1 stop5h 38m
Delta
Deal found 5/17![Delta logo]()
$503
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.
Thu 7/25:10 pm
HPN
- ORD
1 stop4h 21m
Delta
Thu 7/95:30 am
ORD
- HPN
1 stop5h 38m
Delta
Deal found 5/17![Delta logo]()
$503
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 9/1012:45 pm
HPN
- MDW
1 stop6h 46m
Delta
Sun 9/136:00 am
MDW
- HPN
1 stop5h 13m
Delta
Deal found 5/21![Delta logo]()
$531
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 9/114:19 pm
HPN
- MDW
1 stop6h 27m
Delta
Sun 9/136:00 am
MDW
- HPN
1 stop5h 13m
Delta
Deal found 5/17![Delta logo]()
$531
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 7/314:29 pm
HPN
- MDW
1 stop6h 46m
Delta
Sun 8/29:19 am
MDW
- HPN
1 stop5h 28m
Delta
Deal found 5/21![Delta logo]()
$531
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.
Thu 6/185:10 pm
HPN
- ORD
1 stop4h 21m
Delta
Sun 6/215:30 am
ORD
- HPN
1 stop5h 39m
Delta
Deal found 5/18![Delta logo]()
$531
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.
Wed 6/1012:38 pm
HPN
- ORD
1 stop4h 48m
Delta
Tue 6/167:01 am
ORD
- HPN
1 stop3h 57m
Delta
Deal found 5/19![Delta logo]()
$575
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 7/2912:36 pm
HPN
- ORD
1 stop6h 53m
Delta
Sun 8/26:30 am
ORD
- HPN
2 stops8h 17m
Delta
Deal found 5/17![Delta logo]()
$612
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 6/134:29 pm
HPN
- MDW
1 stop6h 48m
Delta
Tue 6/161:26 pm
MDW
- HPN
2 stops7h 59m
Delta
Deal found 5/17![Delta logo]()
$632
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 9/2412:45 pm
HPN
- MDW
2 stops10h 01m
Delta
Sun 9/276:00 am
MDW
- HPN
1 stop5h 13m
Delta
Deal found 5/21![Delta logo]()
$646
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 9/1010:29 am
HPN
- ORD
1 stop7h 16m
Delta
Sun 9/139:30 am
ORD
- HPN
2 stops11h 12m
Delta
Deal found 5/21![Delta logo]()
$646
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.
Fri 7/1712:54 pm
HPN
- ORD
2 stops8h 37m
Delta
Sun 7/195:30 am
ORD
- HPN
1 stop5h 38m
Delta
Deal found 5/18![Delta logo]()
$656
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.
Thu 7/306:29 am
HPN
- ORD
2 stops11h 30m
Delta
Sun 8/25:30 am
ORD
- HPN
1 stop5h 38m
Delta
Deal found 5/17![Delta logo]()
$656
Last-minute flights from White Plains to ChicagoDiscover last-minute flight deals from White Plains to Chicago. Data last updated May 22, 2026 and is based on user searches.
Discover last-minute flight deals from White Plains to Chicago. 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 5/234:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Wed 5/2710:59 am
MDW
- HPN
1 stop6h 01m
Delta
Deal found 5/21![Delta logo]()
$445
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 5/234:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Sat 5/309:22 am
MDW
- HPN
1 stop5h 27m
Delta
Deal found 5/20![Delta logo]()
$475
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 5/235:15 pm
HPN
- ORD
1 stop3h 59m
Delta
Sat 5/307:00 am
ORD
- HPN
1 stop3h 51m
Delta
Deal found 5/20![Delta logo]()
$475
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.
Thu 5/286:40 pm
HPN
- ORD
1 stop6h 19m
Delta
Sat 5/303:00 pm
ORD
- HPN
1 stop6h 20m
Delta
Deal found 5/20![Delta logo]()
$445
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.
Fri 5/296:30 am
HPN
- ORD
1 stop4h 24m
American Airlines
Wed 6/37:37 pm
ORD
- HPN
Nonstop2h 21m
American Airlines
Deal found 5/21![American Airlines logo]()
$435
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.
Fri 5/297:10 am
HPN
- ORD
Nonstop2h 43m
American Airlines
Sun 5/318:10 am
ORD
- HPN
Nonstop2h 19m
American Airlines
Deal found 5/21![American Airlines logo]()
$469
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.
Fri 5/296:00 am
HPN
- MDW
1 stop6h 56m
Delta
Mon 6/19:22 am
MDW
- HPN
1 stop5h 27m
Delta
Deal found 5/19![Delta logo]()
$489
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.
Thu 6/412:31 pm
HPN
- MDW
1 stop7h 02m
Delta
Sat 6/69:22 am
MDW
- HPN
1 stop5h 27m
Delta
Deal found 5/18![Delta logo]()
$519
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/137:24 am
HPN
- ORD
Nonstop2h 41m
American Airlines
Tue 6/168:10 am
ORD
- HPN
Nonstop2h 19m
American Airlines
Deal found 5/19![American Airlines logo]()
$455
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.
Thu 6/256:19 am
HPN
- ORD
Nonstop2h 41m
American Airlines
Sat 6/276:21 pm
ORD
- HPN
Nonstop2h 28m
American Airlines
Deal found 5/20![American Airlines logo]()
$439
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 6/256:29 am
HPN
- ORD
1 stop7h 07m
Delta
Sat 6/275:30 am
ORD
- HPN
1 stop7h 58m
Delta
Deal found 5/19![Delta logo]()
$459
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.
Thu 6/255:46 pm
HPN
- ORD
Nonstop2h 54m
American Airlines
Sun 6/2812:42 pm
ORD
- HPN
Nonstop2h 17m
American Airlines
Deal found 5/21![American Airlines logo]()
$483
One-way flights from White Plains to ChicagoSearch for one-way flight options from White Plains to Chicago. Find affordable one-way fares based on user searches. Data last updated May 22, 2026.
Search for one-way flight options from White Plains to Chicago. 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 5/18. 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 8/106:09 pm
HPN
- ORD
2 stops26h 44m
Multiple Airlines
Deal found 5/18![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.
Tue 8/181:29 pm
HPN
- ORD
2 stops43h 34m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$146
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.
Mon 8/176:09 pm
HPN
- ORD
2 stops26h 46m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$149
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.
Sun 8/308:00 am
HPN
- ORD
2 stops25h 03m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$151
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.
Mon 7/136:09 pm
HPN
- ORD
2 stops26h 44m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$155
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1412:27 pm
HPN
- ORD
2 stops11h 43m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$156
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.
Sun 8/168:00 am
HPN
- ORD
2 stops24h 53m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$162
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.
Mon 9/217:40 pm
HPN
- ORD
2 stops29h 15m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$163
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 6/86:09 pm
HPN
- MDW
2 stops29h 02m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$177
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.
Sun 7/128:00 am
HPN
- ORD
2 stops48h 53m
Multiple Airlines
Deal found 5/19![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.
Mon 11/167:40 pm
HPN
- ORD
2 stops29h 10m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$179
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.
Mon 9/217:40 pm
HPN
- MDW
3 stops40h 18m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$180
Find flight deals from White Plains to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from White Plains (HPN) to Chicago (CHI). 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 | $435 (American Airlines) |
One-way from | $138 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $515 |
Good round-trip deal | $472 or less |
Good one-way deal | $278 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from White Plains to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 22, 2026.
Use the filters below to find and compare flights from White Plains to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
Wed 7/29
4:29 pm-10:15 pm
1 stop6h 46m
Chicago Midway
Sun 8/2
9:19 am-3:47 pm
1 stop5h 28m
$487
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Thu 7/23
6:00 am-10:10 am
1 stop5h 10m
Chicago O'Hare Intl
Tue 7/28
8:03 am-2:29 pm
1 stop5h 26m
$487
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
Fri 7/24
4:29 pm-10:15 pm
1 stop6h 46m
Chicago Midway
Sun 7/26
6:00 am-12:08 pm
1 stop5h 08m
$503
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
Fri 9/25
4:19 pm-9:46 pm
1 stop6h 27m
Chicago Midway
Sun 9/27
6:00 am-12:13 pm
1 stop5h 13m
$503
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Fri 9/11
3:15 pm-9:34 pm
1 stop7h 19m
Chicago O'Hare Intl
Sun 9/13
5:30 am-12:13 pm
1 stop5h 43m
$503
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Fri 7/31
12:36 pm-4:23 pm
1 stop4h 47m
Chicago O'Hare Intl
Sun 8/2
5:30 am-12:08 pm
1 stop5h 38m
$503
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Thu 7/2
5:10 pm-8:31 pm
1 stop4h 21m
Chicago O'Hare Intl
Thu 7/9
5:30 am-12:08 pm
1 stop5h 38m
$503
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
Thu 9/10
12:45 pm-6:31 pm
1 stop6h 46m
Chicago Midway
Sun 9/13
6:00 am-12:13 pm
1 stop5h 13m
$531
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
Fri 9/11
4:19 pm-9:46 pm
1 stop6h 27m
Chicago Midway
Sun 9/13
6:00 am-12:13 pm
1 stop5h 13m
$531
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
Fri 7/31
4:29 pm-10:15 pm
1 stop6h 46m
Chicago Midway
Sun 8/2
9:19 am-3:47 pm
1 stop5h 28m
$531
Showing 1-10 of 38 resultsSorted by cheapest first
Compare providers for flights from White Plains to Chicago
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 White Plains to Chicago 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 White Plains-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on White Plains-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from White Plains-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on White Plains-Chicago 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 White Plains-Chicago 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 White Plains to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from White Plains with our price prediction graph.
HPN-CHI
HPN-MDW
HPN-ORD
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 White Plains to Chicago
HPN-CHI
HPN-MDW
HPN-ORD
What is the cheapest month to book a flight from White Plains to Chicago?
Currently, January is the cheapest month in which you can book a flight from White Plains to Chicago (average of $52). Flying from White Plains to Chicago in May is currently the most expensive (average of $349). 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 HPN to CHI?
Find hourly flight availability from White Plains to Chicago. 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.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from White Plains to Chicago as you normally would.
Weekly flight availability from White Plains to Chicago
Explore weekly flight availability from White Plains to Chicago. 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 HPN to CHI are scheduled on a Thursday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).
How much does it cost to fly round-trip from White Plains to Chicago?
How far ahead should I book a flight from White Plains to Chicago?
The best time to book flights from White Plains to Chicago is 71 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated May 22, 2026.
Peruse reviews from past customers who have flown with Delta and American Airlines from White Plains to Chicago 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
8.1
Overall
7.9
Comfort
7.8
Crew
8.5
Food
7.2
Entertainment
7.8
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Boarding
8.1
Overall
7.9
Comfort
7.8
Crew
8.5
Food
7.2
Entertainment
7.8
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Boarding
8.1
Overall
7.9
Comfort
7.8
Crew
8.5
Food
7.2
Entertainment
7.8
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Related info for your journey
Find useful and relevant information for your journey from White Plains to Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 22, 2026.
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White Plains and Chicago flights
Browse other White Plains and Chicago flight options. Last updated on May 22, 2026.
Other flights from White Plains
Browse through other flights departing from White Plains. Flights are based on user searches made on Cheapflights and were last updated on May 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from White Plains to Chicago
Discover the top airline that operate flights from White Plains to Chicago. 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$501 | FlexibilityNo cancel fee | On-time71% |