$141+ Cheap flights from White Plains (HPN) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Nov 15 — Nov 221
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 23 days in advance, depart on a Saturday or Wednesday and return on a Saturday
Cheap flight deals from White Plains to Chicago
Cheapest
Best
Last-minute
One-way
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 October 16, 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 October 16, 2026.
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/275:22 pm -
1 stop4h 08m
Wed 11/410:55 am -
1 stop3h 53m
Deal found 10/14![Delta logo]()
$400
This American Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/114:36 pm -
Nonstop2h 54m
Sat 11/146:37 pm -
Nonstop2h 22m
Deal found 10/11![American Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/1412:30 pm -
1 stop4h 48m
Sun 11/157:05 am -
1 stop3h 44m
Deal found 10/14![Delta logo]()
$410
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 12/95:15 pm -
2 stops7h 41m
Sun 12/135:30 am -
1 stop5h 44m
Deal found 10/14![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/113:10 pm -
1 stop7h 23m
Tue 11/178:04 am -
1 stop5h 25m
Deal found 10/12![Delta logo]()
$421
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/275:22 pm -
1 stop4h 08m
Tue 11/37:00 am -
1 stop3h 50m
Deal found 10/14![Delta logo]()
$425
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/135:16 pm -
2 stops7h 38m
Sun 11/157:05 am -
1 stop3h 44m
Deal found 10/13![Delta logo]()
$426
This American Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 12/234:38 pm -
Nonstop2h 51m
Tue 12/296:33 pm -
Nonstop2h 26m
Deal found 10/12![American Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/145:27 pm -
1 stop7h 02m
Tue 11/1712:45 pm -
Nonstop2h 14m
Deal found 10/14![American Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/36:40 pm -
1 stop6h 17m
Wed 11/255:05 pm -
1 stop17h 44m
Deal found 10/13![Delta logo]()
$432
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 October 16, 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 October 16, 2026.
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 12/115:15 pm -
1 stop4h 00m
Sun 12/135:30 am -
1 stop5h 44m
Deal found 10/15![Delta logo]()
$421
This United deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:11 am -
3 stops14h 07m
Tue 11/108:07 pm -
2 stops19h 52m
Deal found 10/13![Multiple Airlines logo]()
$719
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/54:29 pm -
1 stop8h 28m
Tue 11/108:04 am -
1 stop5h 25m
Deal found 10/15![Delta logo]()
$435
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/196:45 pm -
1 stop6h 09m
Sun 11/226:49 am -
1 stop6h 40m
Deal found 10/14![Delta logo]()
$435
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/26:40 pm -
1 stop6h 17m
Mon 11/97:05 am -
1 stop3h 44m
Deal found 10/15![Delta logo]()
$460
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/203:10 pm -
1 stop5h 29m
Sun 11/225:30 am -
1 stop5h 43m
Deal found 10/15![Delta logo]()
$484
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/85:22 pm -
1 stop4h 08m
Wed 11/187:05 am -
1 stop3h 44m
Deal found 10/14![Delta logo]()
$563
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 12/46:00 am -
2 stops11h 43m
Mon 12/79:59 am -
1 stop5h 36m
Deal found 10/15![Delta logo]()
$598
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 1/3012:59 pm -
1 stop6h 33m
Tue 2/27:00 am -
2 stops10h 07m
Deal found 10/15![Delta logo]()
$598
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/116:00 am -
2 stops8h 59m
Sun 11/156:23 am -
2 stops10h 38m
Deal found 10/13![Delta logo]()
$623
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:30 pm -
2 stops7h 41m
Mon 11/26:30 am -
2 stops8h 18m
Deal found 10/13![Delta logo]()
$628
Last-minute flights from White Plains to ChicagoDiscover last-minute flight deals from White Plains to Chicago. Data last updated October 16, 2026 and is based on user searches.
Discover last-minute flight deals from White Plains to Chicago. Data last updated October 16, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/275:22 pm -
1 stop4h 08m
Thu 11/57:00 am -
1 stop3h 50m
Deal found 10/14![Delta logo]()
$400
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/275:22 pm -
1 stop4h 08m
Tue 11/37:00 am -
1 stop3h 50m
Deal found 10/14![Delta logo]()
$425
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/36:40 pm -
1 stop6h 17m
Wed 11/255:05 pm -
1 stop17h 44m
Deal found 10/13![Delta logo]()
$432
This American Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/46:05 am -
Nonstop2h 55m
Tue 11/107:29 pm -
Nonstop2h 19m
Deal found 10/11![American Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/114:36 pm -
Nonstop2h 54m
Sat 11/146:37 pm -
Nonstop2h 22m
Deal found 10/11![American Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/113:10 pm -
1 stop7h 23m
Tue 11/178:04 am -
1 stop5h 25m
Deal found 10/12![Delta logo]()
$421
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/126:00 am -
2 stops11h 18m
Sun 11/157:05 am -
1 stop3h 44m
Deal found 10/14![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/135:16 pm -
2 stops7h 38m
Sun 11/157:05 am -
1 stop3h 44m
Deal found 10/13![Delta logo]()
$426
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/143:10 pm -
1 stop7h 23m
Sun 11/155:30 am -
1 stop5h 43m
Deal found 10/14![Delta logo]()
$410
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/145:27 pm -
1 stop7h 02m
Tue 11/1712:45 pm -
Nonstop2h 14m
Deal found 10/14![American Airlines logo]()
$431
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 October 16, 2026.
Search for one-way flight options from White Plains to Chicago. Find affordable one-way fares based on user searches. Data last updated October 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 12/117:45 pm -
2 stops23h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 12/147:45 pm -
2 stops23h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 12/37:45 pm -
2 stops36h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 1/107:45 pm -
2 stops41h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 12/47:45 pm -
2 stops23h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$152
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/1112:59 pm -
1 stop6h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 12/97:45 pm -
2 stops26h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/1712:07 pm -
3 stops31h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/167:45 pm -
2 stops23h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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.
Sat 12/127:45 pm -
2 stops36h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$158
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 1/126:00 am -
2 stops11h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/117:45 pm -
2 stops24h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$163
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 October 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $400 (Delta) |
One-way from | $141 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $523 |
Good round-trip deal | $427 or less |
Good one-way deal | $279 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 October 16, 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 - ORD Chicago O'Hare Intl
HPNORD
White Plains Westchester County
Thu 11/12
6:45 pm-11:54 pm
1 stop6h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$154
Quickest round-trip
White PlainsChicago
HPN White Plains Westchester County - ORD Chicago O'Hare Intl
HPNORD
White Plains Westchester County
Tue 4/13
3:15 pm-7:34 pm
1 stop5h 19m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$154
White PlainsChicago
HPN White Plains Westchester County - ORD Chicago O'Hare Intl
HPNORD
White Plains Westchester County
Mon 4/12
6:40 pm-11:50 pm
1 stop6h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$154
White PlainsChicago
HPN White Plains Westchester County - ORD Chicago O'Hare Intl
HPNORD
White Plains Westchester County
Mon 11/16
6:00 am-12:20 pm
1 stop7h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$154
White PlainsChicago
HPN White Plains Westchester County - ORD Chicago O'Hare Intl
HPNORD
White Plains Westchester County
Mon 11/9
12:30 pm-6:30 pm
1 stop7h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$154
White PlainsChicago
HPN White Plains Westchester County - ORD Chicago O'Hare Intl
HPNORD
White Plains Westchester County
Wed 11/11
12:58 pm-7:05 pm
1 stop7h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
White PlainsChicago
HPN White Plains Westchester County - ORD Chicago O'Hare Intl
HPNORD
White Plains Westchester County
Sat 2/6
6:00 am-4:37 pm
2 stops11h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
White PlainsChicago
HPN White Plains Westchester County - ORD Chicago O'Hare Intl
HPNORD
White Plains Westchester County
Sat 11/14
12:30 pm-9:33 pm
2 stops10h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
White PlainsChicago
HPN White Plains Westchester County - ORD Chicago O'Hare Intl
HPNORD
White Plains Westchester County
Fri 12/11
5:15 pm-8:15 pm
1 stop4h 00m
Chicago O'Hare Intl
Sun 12/13
5:30 am-12:14 pm
1 stop5h 44m
$421
White PlainsChicago
HPN White Plains Westchester County - ORD Chicago O'Hare Intl
HPNORD
White Plains Westchester County
Thu 11/5
4:29 pm-11:57 pm
1 stop8h 28m
Chicago O'Hare Intl
Tue 11/10
8:04 am-2:29 pm
1 stop5h 25m
$435
Showing 1-10 of 19 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 October.
| 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-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-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 $463). 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 October 16, 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 October 16, 2026.
The most flights from HPN to CHI are scheduled on a Wednesday (9 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (7 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 $475 and $592 in March.The cheapest round-trip price found within the last 5 days was $400 on Delta (Mar 6-Mar 20).
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 89 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 October 16, 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
Overall
7.8
Boarding
8.1
Comfort
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Entertainment
7.8
Overall
7.8
Boarding
8.1
Comfort
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Entertainment
7.8
Overall
7.8
Boarding
8.1
Comfort
7.8
Food
7.2
Crew
8.5
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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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 October 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$387 | Average$520 | FlexibilityNo cancel fee | On-time71% |