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White Plains

$74+ Cheap flights from Chicago (CHI) to White Plains (HPN)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Dec 19 — Dec 261
Fri 12/19
Fri 12/26
1 adult, Economy
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Find flight deals from Chicago to White Plains

Cheapest flights from Chicago to White Plains
Explore the most affordable flight options available from Chicago to White Plains. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 19, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
Thu 12/117:40 amORD - HPN
1 stop26h 48mMultiple Airlines
Mon 12/158:00 amHPN - ORD
2 stops37h 01mMultiple Airlines
Deal found 11/18$318
This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
Thu 12/117:40 amORD - HPN
1 stop26h 48mMultiple Airlines
Tue 12/168:00 amHPN - ORD
2 stops37h 01mMultiple Airlines
Deal found 11/18$325
This American Airlines deal was found by Cheapflights users on 11/19. 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 12/202:13 pmORD - HPN
Nonstop2h 13mAmerican Airlines
Sat 1/1712:00 pmHPN - ORD
Nonstop2h 45mAmerican Airlines
Deal found 11/19$349
This American Airlines deal was found by Cheapflights users on 11/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/218:10 amORD - HPN
Nonstop2h 19mAmerican Airlines
Tue 12/304:30 pmHPN - ORD
Nonstop2h 52mAmerican Airlines
Deal found 11/18$380
This American Airlines deal was found by Cheapflights users on 11/19. 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 12/202:13 pmORD - HPN
Nonstop2h 13mAmerican Airlines
Mon 12/296:30 amHPN - ORD
1 stop5h 20mAmerican Airlines
Deal found 11/19$390
This Kiwi.com deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:00 amORD - HPN
2 stops30h 39mMultiple Airlines
Fri 12/1212:10 pmHPN - ORD
1 stop9h 32mMultiple Airlines
Deal found 11/18$394
This Delta deal was found by Cheapflights users on 11/17. 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 12/317:00 amORD - HPN
1 stop3h 59mDelta
Thu 1/112:55 pmHPN - ORD
1 stop8h 41mDelta
Deal found 11/17$407
This American Airlines deal was found by Cheapflights users on 11/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/201:12 pmORD - HPN
1 stop6h 15mAmerican Airlines
Sat 1/106:00 amHPN - ORD
Nonstop2h 52mAmerican Airlines
Deal found 11/18$409
This Delta deal was found by Cheapflights users on 11/18. 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 12/910:49 amMDW - HPN
1 stop10h 20mDelta
Tue 12/1612:45 pmHPN - MDW
1 stop4h 59mDelta
Deal found 11/18$426
This Delta deal was found by Cheapflights users on 11/17. 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.
Sun 12/219:29 amMDW - HPN
1 stop5h 20mDelta
Mon 12/296:03 amHPN - MDW
1 stop6h 55mDelta
Deal found 11/17$465
This Delta deal was found by Cheapflights users on 11/18. 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.
Wed 12/109:59 amMDW - HPN
1 stop5h 38mDelta
Tue 12/1612:45 pmHPN - MDW
1 stop4h 59mDelta
Deal found 11/18$469
This Delta deal was found by Cheapflights users on 11/17. 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.
Tue 12/309:29 amMDW - HPN
1 stop5h 20mDelta
Sat 1/312:55 pmHPN - MDW
1 stop5h 31mDelta
Deal found 11/17$499

Cheap flight deals from Chicago to White Plains

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to White Plains (HPN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 19, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$217
(Kiwi.com)

One-way from

$74
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$543

Good round-trip deal

$452 or less

Good one-way deal

$398 or less
Provider with most accurate pricing for Chicago (CHI)-White Plains Westchester County flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-White Plains Westchester County flights.
Search Deals
From Chicago (CHI) to White Plains Westchester County
Search Deals
One-way flight from Chicago (CHI) to White Plains Westchester County
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to White Plains Westchester County.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to White Plains Westchester County.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to White Plains that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 19, 2025.
Use the filters below to find and compare flights from Chicago to White Plains that are best for you.

Fly from

Chicago

Fly to

White Plains

Route

Depart

Return

Price

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 4/1

11:55 am-6:17 pm

1 stop5h 22m

White Plains Westchester County

Wed 4/8

7:34 am-9:10 am

Nonstop2h 36m

$359

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 3/14

5:50 am-12:11 pm

1 stop5h 21m

White Plains Westchester County

Tue 3/17

12:45 pm-6:46 pm

1 stop7h 01m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 3/11

7:10 am-2:33 pm

1 stop6h 23m

White Plains Westchester County

Tue 3/17

3:15 pm-7:56 pm

1 stop5h 41m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 3/11

10:35 am-4:35 pm

1 stop5h 00m

White Plains Westchester County

Wed 3/18

6:40 pm-11:54 pm

1 stop6h 14m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 4/28

9:30 am-4:40 pm

1 stop6h 10m

White Plains Westchester County

Tue 5/5

5:10 pm-8:35 pm

1 stop4h 25m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 4/4

9:30 am-4:40 pm

1 stop6h 10m

White Plains Westchester County

Tue 4/7

5:10 pm-8:38 pm

1 stop4h 28m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 1/7

6:50 am-11:56 am

1 stop4h 06m

White Plains Westchester County

Sat 1/10

3:10 pm-9:43 pm

1 stop7h 33m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 4/29

9:30 am-6:12 pm

1 stop7h 42m

White Plains Westchester County

Wed 5/6

3:15 pm-7:43 pm

1 stop5h 28m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 4/29

10:35 am-4:33 pm

1 stop4h 58m

White Plains Westchester County

Sat 5/2

4:19 pm-11:55 pm

1 stop8h 36m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 4/1

7:00 am-11:50 am

1 stop3h 50m

White Plains Westchester County

Wed 4/8

12:45 pm-6:46 pm

1 stop7h 01m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 41 results
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Compare providers for flights from Chicago to White Plains

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to White Plains in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-White Plains flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-White Plains flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-White Plains flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-White Plains flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-White Plains flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to White Plains

Have a flexible travel schedule? Discover the best time to fly to White Plains from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to White Plains

What is the cheapest month to book a flight from Chicago to White Plains?

Currently, January is the cheapest month in which you can book a flight from Chicago to White Plains (average of $37). Flying from Chicago to White Plains in July is currently the most expensive (average of $104). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to HPN?

Find hourly flight availability from Chicago to White Plains. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 19, 2025.

It’s typically best to fly out from Chicago to White Plains in the morning. Doing so could potentially save you 6% on the flight price compared to flying in the evening, which is usually more expensive.

Weekly flight availability from Chicago to White Plains

Explore weekly flight availability from Chicago to White Plains. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 19, 2025.

The most flights from CHI to HPN are scheduled on a Monday (8 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (6 on average).

Reviews of airlines servicing White Plains

Get insights into the airlines that provide service to White Plains. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to White Plains. Reviews last updated November 19, 2025.
Peruse reviews from past customers who have flown with Delta and American Airlines from Chicago to White Plains to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,004 reviews

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
Delta
7.9
Good
8,004 reviews
Delta
7.9
Good
8,004 reviews

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
American Airlines
7.2
Good
11,046 reviews
Delta
7.9
Good
8,004 reviews

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Chicago to White Plains. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to White Plains from Chicago?

    Located just 3.7 mi from the city center, White Plains Westchester County is the airport most travelers will use when flying to White Plains from Chicago. Booking flights from Chicago to Westchester County (HPN) should be relatively easy as there are 7 daily inbound flights from Chicago from 1 airline.

  • How long is the flight from Chicago to White Plains?

    Airlines like American Airlines and Delta fly from Chicago to White Plains in about 5h 21m. The time it takes to get you to your destination can typically vary by up to 01m. There are 736 mi between Chicago and White Plains. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Chicago to White Plains round-trip?

    According to our current data, American Airlines ($374), offers the cheapest pricing from Chicago to White Plains. American Airlines is 17% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the most reliable airlines from Chicago to White Plains?

    Before booking your flight to White Plains from Chicago, check out the most reliable airlines to get you to your destination on time: Qatar Airways (84%), Alaska Airlines (80%), American Airlines( 79%).

  • What are the cheapest flights from Chicago to White Plains?

    On average you can expect to pay $510 for a flight from Chicago to White Plains. The cheapest flight overall is $288 while the most popular route, (Chicago O'Hare Intl - White Plains Westchester County) is currently priced at $275.

  • Can I find deals for flights from Chicago to White Plains that include hotel bookings?

    Yes. In addition to deals on Chicago to White Plains flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to White Plains?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to White Plains.

  • Can I find deals for business class flights from Chicago to White Plains?

    Yes. Cheapflights offers flight deals from Chicago to White Plains by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to White Plains?

    Currently, January is the cheapest month in which you can book a flight from Chicago to White Plains (average of $37). Flying from Chicago to White Plains in July is currently the most expensive (average of $104). 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.

See more FAQs

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Alternative routes for Chicago to White Plains

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Chicago to White Plains

Discover the top airline that operate flights from Chicago to White Plains. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$374Average$465FlexibilityNo cancel feeOn-time71%

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