$144+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Sep 27 — Oct 41
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 August, booked 85 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 August 28, 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 August 28, 2026.
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/214:29 pm -
1 stop7h 04m
Sat 10/246:04 am -
1 stop7h 25m
Deal found 8/23![Delta logo]()
$381
This American Airlines deal was found by Cheapflights users on 8/25. 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 10/74:30 pm -
Nonstop2h 52m
Wed 10/147:30 pm -
Nonstop2h 26m
Deal found 8/25![American Airlines logo]()
$381
This American Airlines deal was found by Cheapflights users on 8/26. 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 10/107:21 am -
Nonstop2h 44m
Sat 10/172:00 pm -
Nonstop2h 24m
Deal found 8/26![American Airlines logo]()
$382
This CheapOair deal was found by Cheapflights users on 8/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:30 am -
1 stop16h 27m
Tue 10/272:42 pm -
1 stop7h 17m
Deal found 8/24![JetBlue logo]()
$390
This American Airlines deal was found by Cheapflights users on 8/25. 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 12/912:13 pm -
Nonstop2h 46m
Sun 12/1312:45 pm -
Nonstop2h 14m
Deal found 8/25![American Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:06 am -
Nonstop2h 44m
Sun 9/278:05 am -
Nonstop2h 24m
Deal found 8/25![American Airlines logo]()
$398
This Expedia deal was found by Cheapflights users on 8/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:59 am -
1 stop13h 31m
Mon 10/262:42 pm -
1 stop7h 17m
Deal found 8/24![JetBlue logo]()
$400
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/712:30 pm -
1 stop6h 30m
Wed 10/146:04 am -
1 stop5h 04m
Deal found 8/25![Delta logo]()
$401
This American Airlines deal was found by Cheapflights users on 8/27. 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 10/1011:01 am -
1 stop6h 59m
Tue 10/134:50 pm -
1 stop5h 39m
Deal found 8/27![American Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 8/25. 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 9/226:40 pm -
1 stop5h 04m
Sat 9/266:05 am -
1 stop7h 24m
Deal found 8/25![Delta logo]()
$407
This JetBlue deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/94:25 pm -
1 stop8h 03m
Sun 12/132:50 pm -
1 stop7h 10m
Deal found 8/24![JetBlue logo]()
$407
This American Airlines deal was found by Cheapflights users on 8/24. 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 9/64:30 pm -
Nonstop2h 49m
Wed 9/91:44 pm -
Nonstop2h 21m
Deal found 8/24![American Airlines logo]()
$413
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 August 28, 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 August 28, 2026.
This Delta deal was found by Cheapflights users on 8/23. 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 10/2012:30 pm -
1 stop6h 30m
Sat 10/246:04 am -
1 stop4h 59m
Deal found 8/23![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 8/23. 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 9/226:40 pm -
1 stop6h 19m
Tue 9/298:55 am -
1 stop5h 50m
Deal found 8/23![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 8/23. 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 10/276:40 pm -
1 stop6h 17m
Sat 10/316:30 am -
1 stop6h 59m
Deal found 8/23![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 8/23. 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 12/96:40 pm -
1 stop5h 15m
Sun 12/136:00 am -
1 stop5h 14m
Deal found 8/23![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 8/27. 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 9/223:10 pm -
1 stop7h 23m
Sat 9/265:30 am -
1 stop7h 59m
Deal found 8/27![Delta logo]()
$427
This Delta deal was found by Cheapflights users on 8/23. 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 10/276:00 am -
2 stops7h 47m
Sat 10/319:29 am -
1 stop5h 19m
Deal found 8/23![Delta logo]()
$435
This Delta deal was found by Cheapflights users on 8/26. 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 10/244:29 pm -
1 stop7h 04m
Mon 10/269:29 am -
1 stop5h 19m
Deal found 8/26![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/214:29 pm -
1 stop7h 04m
Mon 10/269:29 am -
1 stop5h 19m
Deal found 8/27![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 8/24. 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 10/235:22 pm -
1 stop6h 11m
Mon 10/269:29 am -
1 stop5h 19m
Deal found 8/24![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 8/24. 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 12/116:40 pm -
1 stop5h 15m
Sun 12/139:37 am -
1 stop5h 11m
Deal found 8/24![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 8/24. 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 9/312:48 pm -
2 stops9h 59m
Sat 9/51:50 pm -
1 stop7h 31m
Deal found 8/24![Delta logo]()
$461
This Delta deal was found by Cheapflights users on 8/25. 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 9/912:50 pm -
1 stop6h 51m
Sun 9/135:30 am -
1 stop5h 33m
Deal found 8/25![Delta logo]()
$468
This Delta deal was found by Cheapflights users on 8/23. 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 11/56:00 am -
2 stops7h 59m
Mon 11/96:49 am -
1 stop6h 40m
Deal found 8/23![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 8/24. 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 9/84:25 pm -
1 stop7h 19m
Wed 9/911:35 am -
1 stop5h 25m
Deal found 8/24![Delta logo]()
$479
This Delta deal was found by Cheapflights users on 8/24. 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 9/295:20 pm -
1 stop4h 10m
Thu 10/18:55 am -
1 stop5h 50m
Deal found 8/24![Delta logo]()
$479
This Delta deal was found by Cheapflights users on 8/24. 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 9/312:48 pm -
2 stops9h 59m
Mon 9/76:59 am -
1 stop3h 57m
Deal found 8/24![Delta logo]()
$484
This Delta deal was found by Cheapflights users on 8/24. 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 9/2312:50 pm -
2 stops9h 43m
Fri 9/253:40 pm -
1 stop5h 35m
Deal found 8/24![Delta logo]()
$484
This Delta deal was found by Cheapflights users on 8/27. 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 9/116:00 am -
1 stop5h 36m
Mon 9/149:24 am -
1 stop5h 21m
Deal found 8/27![Delta logo]()
$488
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/124:25 pm -
1 stop7h 19m
Mon 9/149:24 am -
1 stop5h 21m
Deal found 8/27![Delta logo]()
$488
This Delta deal was found by Cheapflights users on 8/27. 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 10/212:40 pm -
1 stop4h 33m
Mon 10/55:30 am -
1 stop5h 33m
Deal found 8/27![Delta logo]()
$498
Last-minute flights from White Plains to ChicagoDiscover last-minute flight deals from White Plains to Chicago. Data last updated August 28, 2026 and is based on user searches.
Discover last-minute flight deals from White Plains to Chicago. Data last updated August 28, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/24. 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 9/64:30 pm -
Nonstop2h 49m
Wed 9/91:44 pm -
Nonstop2h 21m
Deal found 8/24![American Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 8/24. 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 9/66:00 am -
1 stop5h 10m
Wed 9/99:29 am -
1 stop5h 16m
Deal found 8/24![Delta logo]()
$433
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:00 am -
Nonstop2h 44m
Wed 9/165:00 pm -
1 stop5h 26m
Deal found 8/24![American Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 8/25. 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 9/95:20 pm -
1 stop4h 10m
Sat 9/121:51 pm -
1 stop7h 24m
Deal found 8/25![Delta logo]()
$433
This Delta deal was found by Cheapflights users on 8/24. 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 9/114:25 pm -
1 stop7h 19m
Mon 9/149:24 am -
1 stop5h 21m
Deal found 8/24![Delta logo]()
$456
This American Airlines deal was found by Cheapflights users on 8/23. 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 9/184:30 pm -
Nonstop2h 47m
Tue 9/228:05 am -
Nonstop2h 24m
Deal found 8/23![American Airlines logo]()
$422
This Delta deal was found by Cheapflights users on 8/23. 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 9/226:40 pm -
1 stop6h 19m
Tue 9/298:55 am -
1 stop5h 50m
Deal found 8/23![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 8/25. 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 9/226:40 pm -
1 stop5h 04m
Sat 9/266:05 am -
1 stop7h 24m
Deal found 8/25![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 8/25. 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 9/223:10 pm -
1 stop7h 23m
Sat 9/265:30 am -
1 stop7h 59m
Deal found 8/25![Delta logo]()
$407
This American Airlines deal was found by Cheapflights users on 8/27. 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 9/226:00 am -
Nonstop2h 44m
Sat 9/261:22 pm -
1 stop4h 04m
Deal found 8/27![American Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 8/24. 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 9/234:25 pm -
1 stop7h 19m
Wed 9/306:05 am -
1 stop4h 58m
Deal found 8/24![Delta logo]()
$381
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals ”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:06 am -
Nonstop2h 44m
Sun 9/278:05 am -
Nonstop2h 24m
Deal found 8/25![American Airlines logo]()
$397
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 August 28, 2026.
Search for one-way flight options from White Plains to Chicago. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:45 pm -
2 stops44h 00m
Deal found 8/23![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/227:45 pm -
3 stops40h 55m
Deal found 8/23![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 10/217:45 pm -
2 stops44h 51m
Deal found 8/23![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 9/297:45 pm -
3 stops44h 00m
Deal found 8/24![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 10/277:45 pm -
3 stops40h 38m
Deal found 8/24![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:45 pm -
2 stops23h 38m
Deal found 8/26![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 9/287:45 pm -
3 stops44h 35m
Deal found 8/24![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:45 pm -
2 stops23h 01m
Deal found 8/24![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 9/297:45 pm -
2 stops23h 06m
Deal found 8/24![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/81:29 pm -
2 stops29h 22m
Deal found 8/26![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:45 pm -
2 stops23h 01m
Deal found 8/24![Multiple Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 9/287:45 pm -
2 stops23h 01m
Deal found 8/24![Multiple Airlines logo]()
$200
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 August 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $381 (Delta) |
One-way from | $144 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $439 |
Good round-trip deal | $421 or less |
Good one-way deal | $298 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 7,457,451 searches. Data last updated August 28, 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 White Plains Westchester County - MDW Chicago Midway
HPNMDW
White Plains Westchester County
Tue 10/20
12:30 pm-6:00 pm
1 stop6h 30m
Chicago Midway
Sat 10/24
6:04 am-12:03 pm
1 stop4h 59m
$381
White PlainsChicago
HPN White Plains Westchester County - ORD Chicago O'Hare Intl
HPNORD
White Plains Westchester County
Tue 9/22
6:40 pm-11:59 pm
1 stop6h 19m
Chicago O'Hare Intl
Tue 9/29
8:55 am-3:45 pm
1 stop5h 50m
$381
White PlainsChicago
HPN White Plains Westchester County - ORD Chicago O'Hare Intl
HPNORD
White Plains Westchester County
Tue 10/27
6:40 pm-11:57 pm
1 stop6h 17m
Chicago O'Hare Intl
Sat 10/31
6:30 am-2:29 pm
1 stop6h 59m
$381
White PlainsChicago
HPN White Plains Westchester County - MDW Chicago Midway
HPNMDW
White Plains Westchester County
Wed 12/9
6:40 pm-10:55 pm
1 stop5h 15m
Chicago Midway
Sun 12/13
6:00 am-12:14 pm
1 stop5h 14m
$417
White PlainsChicago
HPN White Plains Westchester County - ORD Chicago O'Hare Intl
HPNORD
White Plains Westchester County
Tue 9/22
3:10 pm-9:33 pm
1 stop7h 23m
Chicago O'Hare Intl
Sat 9/26
5:30 am-2:29 pm
1 stop7h 59m
$427
White PlainsChicago
HPN White Plains Westchester County - MDW Chicago Midway
HPNMDW
White Plains Westchester County
Tue 10/27
6:00 am-12:47 pm
2 stops7h 47m
Chicago Midway
Sat 10/31
9:29 am-3:48 pm
1 stop5h 19m
$435
White PlainsChicago
HPN White Plains Westchester County - MDW Chicago Midway
HPNMDW
White Plains Westchester County
Sat 10/24
4:29 pm-10:33 pm
1 stop7h 04m
Chicago Midway
Mon 10/26
9:29 am-3:48 pm
1 stop5h 19m
$437
White PlainsChicago
HPN White Plains Westchester County - MDW Chicago Midway
HPNMDW
White Plains Westchester County
Wed 10/21
4:29 pm-10:33 pm
1 stop7h 04m
Chicago Midway
Mon 10/26
9:29 am-3:48 pm
1 stop5h 19m
$437
White PlainsChicago
HPN White Plains Westchester County - MDW Chicago Midway
HPNMDW
White Plains Westchester County
Fri 10/23
5:22 pm-10:33 pm
1 stop6h 11m
Chicago Midway
Mon 10/26
9:29 am-3:48 pm
1 stop5h 19m
$453
White PlainsChicago
HPN White Plains Westchester County - MDW Chicago Midway
HPNMDW
White Plains Westchester County
Fri 12/11
6:40 pm-10:55 pm
1 stop5h 15m
Chicago Midway
Sun 12/13
9:37 am-3:48 pm
1 stop5h 11m
$453
Showing 1-10 of 42 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 August.
| 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, August is the cheapest month in which you can book a flight from White Plains to Chicago (average of $465). Flying from White Plains to Chicago in June is currently the most expensive (average of $535). 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 August 28, 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 August 28, 2026.
The most flights from HPN to CHI are scheduled on a Wednesday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from White Plains to Chicago?
Airfare is below average for this route at the moment.
White Plains to Chicago flights typically cost between $419 and $563 in October.The cheapest round-trip price found within the last 5 days was $381 on Delta (Oct 21-Oct 24).
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 69 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 August 28, 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.
Entertainment
7.8
Comfort
7.8
Crew
8.5
Food
7.2
Overall
7.8
Boarding
8.1
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Entertainment
7.8
Comfort
7.8
Crew
8.5
Food
7.2
Overall
7.8
Boarding
8.1
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Entertainment
7.8
Comfort
7.8
Crew
8.5
Food
7.2
Overall
7.8
Boarding
8.1
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
Valparaiso
Hammond
Saint Joseph
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 August 28, 2026.
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White Plains and Chicago flights
Browse other White Plains and Chicago flight options. Last updated on August 28, 2026.
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Browse through other flights departing from White Plains. Flights are based on user searches made on Cheapflights and were last updated on August 28, 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 7,457,451 searches. Data last updated August 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$386 | Average$521 | FlexibilityNo cancel fee | On-time71% |