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White Plains

$102+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
out 29 — nov 51
qua 10/29
qua 11/5
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to White Plains Westchester County are usually found in January or April, booked 81 days in advance, depart on a Tuesday or Saturday and return on a Wednesday

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 setembro 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$295
(Kiwi.com)

One-way from

$102
(Kiwi.com)

Popular in

September

Cheapest in

January

Average price

$493

Good round-trip deal

$420 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.
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From Chicago (CHI) to White Plains Westchester County
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One-way flight from Chicago (CHI) to White Plains Westchester County
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Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to White Plains Westchester County.
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Price to beat on a one-way flight from Chicago (CHI) to White Plains Westchester County.
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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 setembro 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 10/232:41 pmORD - HPN
1 stop19h 47mMultiple Airlines
seg 10/278:25 amHPN - ORD
2 stops31h 20mMultiple Airlines
Deal found 9/27$295
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 11/141:50 pmORD - HPN
2 stops20h 23mMultiple Airlines
seg 11/1712:10 pmHPN - ORD
1 stop12h 18mMultiple Airlines
Deal found 9/27$320
This American Airlines deal was found by Cheapflights users on 9/27. 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.
ter 12/92:12 pmORD - HPN
Nonstop2h 17mAmerican Airlines
sáb 12/134:30 pmHPN - ORD
Nonstop2h 53mAmerican Airlines
Deal found 9/27$349
This Delta deal was found by Cheapflights users on 9/29. 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.
seg 11/177:11 pmORD - HPN
1 stop15h 48mDelta
seg 11/246:41 pmHPN - ORD
1 stop6h 21mDelta
Deal found 9/29$351
This Delta deal was found by Cheapflights users on 9/29. 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.
ter 10/217:10 amORD - HPN
1 stop7h 39mDelta
qua 10/2912:55 pmHPN - ORD
1 stop8h 28mDelta
Deal found 9/29$358
This American Airlines deal was found by Cheapflights users on 9/27. 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.
qua 11/51:15 pmORD - HPN
1 stop3h 58mAmerican Airlines
sáb 11/83:09 pmHPN - ORD
1 stop5h 20mAmerican Airlines
Deal found 9/27$368
This Delta deal was found by Cheapflights users on 9/27. 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.
ter 12/96:45 amORD - HPN
1 stop4h 14mDelta
sáb 12/136:00 amHPN - ORD
1 stop7h 06mDelta
Deal found 9/27$369
This Delta deal was found by Cheapflights users on 9/29. 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.
sáb 12/209:29 amMDW - HPN
1 stop5h 20mDelta
sáb 1/1712:45 pmHPN - MDW
1 stop6h 49mDelta
Deal found 9/29$369
This Delta deal was found by Cheapflights users on 9/29. 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.
ter 10/217:10 amORD - HPN
1 stop7h 39mDelta
sex 10/3112:45 pmHPN - ORD
1 stop7h 04mDelta
Deal found 9/29$376
This American Airlines deal was found by Cheapflights users on 9/27. 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.
sáb 12/202:13 pmORD - HPN
Nonstop2h 13mAmerican Airlines
sáb 1/1712:46 pmHPN - ORD
Nonstop2h 34mAmerican Airlines
Deal found 9/27$379
This American Airlines deal was found by Cheapflights users on 9/27. 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.
sex 10/316:29 pmORD - HPN
Nonstop2h 30mAmerican Airlines
seg 11/35:59 pmHPN - ORD
Nonstop2h 47mAmerican Airlines
Deal found 9/27$380
This Delta deal was found by Cheapflights users on 9/27. 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.
seg 11/179:41 amMDW - HPN
1 stop5h 53mDelta
sáb 11/226:42 pmHPN - MDW
1 stop5h 58mDelta
Deal found 9/27$400

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 setembro 29, 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

ter 12/23

4:13 pm-10:15 pm

1 stop5h 02m

White Plains Westchester County

ter 12/30

12:55 pm-5:22 pm

1 stop5h 27m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

ter 12/9

6:45 am-2:28 pm

1 stop6h 43m

White Plains Westchester County

sáb 12/13

3:08 pm-9:40 pm

1 stop7h 32m

$369

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

sáb 12/20

9:29 am-3:49 pm

1 stop5h 20m

White Plains Westchester County

sáb 1/17

4:19 pm-9:46 pm

1 stop6h 27m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

sáb 12/20

2:13 pm-5:26 pm

Nonstop2h 13m

White Plains Westchester County

sáb 1/17

12:00 pm-1:45 pm

Nonstop2h 45m

$379

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

ter 10/21

7:10 am-3:49 pm

1 stop7h 39m

White Plains Westchester County

ter 10/28

12:55 pm-8:23 pm

1 stop8h 28m

$383

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

sex 10/31

1:25 pm-11:59 am

1 stop21h 34m

White Plains Westchester County

dom 11/2

5:00 am-9:20 am

1 stop5h 20m

$393

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

qua 12/24

1:22 pm-10:15 pm

1 stop7h 53m

White Plains Westchester County

seg 12/29

6:55 pm-12:02 am

1 stop6h 07m

$400

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

ter 12/23

7:00 am-11:59 am

1 stop3h 59m

White Plains Westchester County

seg 12/29

5:16 pm-8:36 pm

1 stop4h 20m

$400

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

dom 12/21

7:00 am-11:59 am

1 stop3h 59m

White Plains Westchester County

sáb 12/27

5:16 pm-8:56 pm

1 stop4h 40m

$400

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

seg 11/17

5:23 am-12:00 pm

1 stop5h 37m

White Plains Westchester County

seg 11/24

6:41 pm-12:02 am

1 stop6h 21m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

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 September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-White Plains flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-White Plains flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-White Plains flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-White Plains flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to White Plains

Have a flexible travel schedule? Discover the best time to fly to White Plains from Chicago with our price prediction graph.
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

How far ahead should I book a flight from Chicago to White Plains?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to White Plains. Price data was last updated on September 26, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to White Plains, you should look to book at least 81 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 $276). Flying from Chicago to White Plains in March is currently the most expensive (average of $339). 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 setembro 29, 2025.

It’s typically best to fly out from Chicago to White Plains in the morning. Doing so could potentially save you 9% 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 setembro 29, 2025.

The most flights from CHI to HPN are scheduled on a Monday (7 on average). You will have fewer flight options on Wednesday, 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 setembro 29, 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
8.0
Very good
7,964 reviews

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
Delta
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

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
10,000 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

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 6 daily inbound flights from Chicago from 1 airline.

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

    Airlines like Delta and American Airlines fly from Chicago to White Plains in about 2h 13m. The time it takes to get you to your destination can typically vary by up to 2h 49m. 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 ($364), offers the cheapest pricing from Chicago to White Plains. American Airlines is 18% 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: Alaska Airlines (84%), Qatar Airways (78%), American Airlines( 77%).

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

    On average you can expect to pay $513 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 $244.

  • 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 $276). Flying from Chicago to White Plains in March is currently the most expensive (average of $339). 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 setembro 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$364Average$458FlexibilityNo cancel feeOn-time71%

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