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White Plains

$200+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to White Plains Westchester County are usually found in September or January, booked 73 days in advance, depart on a Tuesday or Wednesday 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 August 14, 2025.

Round-trip from

$307
(Delta)

One-way from

$200
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$423

Good round-trip deal

$419 or less

Good one-way deal

$316 or less
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. 4% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/14. 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 9/67:15 amORD - HPN
1 stop7h 34mDelta
Tue 9/912:37 pmHPN - ORD
1 stop8h 46mDelta
Deal found 8/14$307
This Delta deal was found by Cheapflights users on 8/14. 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 9/67:15 amORD - HPN
1 stop7h 34mDelta
Mon 9/85:15 pmHPN - ORD
1 stop15h 49mDelta
Deal found 8/14$327
This Delta deal was found by Cheapflights users on 8/14. 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.
Fri 9/511:05 amORD - HPN
1 stop23h 52mDelta
Tue 9/912:37 pmHPN - ORD
1 stop8h 46mDelta
Deal found 8/14$337
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/138:15 amORD - HPN
Nonstop2h 14mAmerican Airlines
Tue 9/167:01 amHPN - ORD
Nonstop2h 32mAmerican Airlines
Deal found 8/14$349
This Delta deal was found by Cheapflights users on 8/14. 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 9/137:20 amORD - HPN
1 stop6h 09mDelta
Tue 9/165:20 pmHPN - ORD
1 stop4h 00mDelta
Deal found 8/14$369
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/308:15 amORD - HPN
Nonstop2h 14mAmerican Airlines
Sun 10/56:00 amHPN - ORD
Nonstop2h 30mAmerican Airlines
Deal found 8/13$380
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/912:49 pmORD - HPN
Nonstop2h 10mAmerican Airlines
Sat 9/137:01 amHPN - ORD
Nonstop2h 32mAmerican Airlines
Deal found 8/13$384
This Delta deal was found by Cheapflights users on 8/13. 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.
Sat 8/307:15 amORD - HPN
1 stop3h 42mDelta
Sun 8/316:00 amHPN - ORD
1 stop7h 16mDelta
Deal found 8/13$404
This Delta deal was found by Cheapflights users on 8/13. 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 11/69:35 amMDW - HPN
1 stop5h 14mDelta
Sun 11/96:00 amHPN - MDW
1 stop6h 55mDelta
Deal found 8/13$431
This Delta deal was found by Cheapflights users on 8/13. 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.
Sat 8/166:04 amMDW - HPN
1 stop4h 56mDelta
Wed 8/203:10 pmHPN - MDW
1 stop7h 34mDelta
Deal found 8/13$439
This Delta deal was found by Cheapflights users on 8/13. 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 8/1510:31 amMDW - HPN
1 stop6h 31mDelta
Wed 8/203:10 pmHPN - MDW
1 stop7h 34mDelta
Deal found 8/13$511
This Delta deal was found by Cheapflights users on 8/13. 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 9/3010:35 amMDW - HPN
1 stop6h 25mDelta
Sun 10/56:00 amHPN - MDW
1 stop6h 48mDelta
Deal found 8/13$559

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 August 14, 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

Sat 9/6

7:15 am-3:49 pm

1 stop7h 34m

White Plains Westchester County

Tue 9/9

12:37 pm-8:23 pm

1 stop8h 46m

$307

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 9/6

7:15 am-3:49 pm

1 stop7h 34m

White Plains Westchester County

Mon 9/8

5:15 pm-8:04 am

1 stop15h 49m

$327

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Fri 9/5

11:05 am-11:57 am

1 stop23h 52m

White Plains Westchester County

Tue 9/9

12:37 pm-8:23 pm

1 stop8h 46m

$337

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 10/1

8:15 am-11:29 am

Nonstop2h 14m

White Plains Westchester County

Sat 10/4

6:00 am-7:30 am

Nonstop2h 30m

$349

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 10/22

2:09 pm-5:27 pm

Nonstop2h 18m

White Plains Westchester County

Sat 10/25

5:57 pm-7:38 pm

Nonstop2h 41m

$349

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 9/13

8:15 am-11:29 am

Nonstop2h 14m

White Plains Westchester County

Tue 9/16

6:00 am-7:30 am

Nonstop2h 30m

$349

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 11/6

9:35 am-3:49 pm

1 stop5h 14m

White Plains Westchester County

Sun 11/9

6:00 am-11:55 am

1 stop6h 55m

$431

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 10/1

6:00 am-11:59 am

1 stop4h 59m

White Plains Westchester County

Sun 10/5

6:00 am-11:48 am

1 stop6h 48m

$559

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 9/30

6:00 am-12:00 pm

1 stop5h 00m

White Plains Westchester County

Sun 10/5

6:00 am-11:48 am

1 stop6h 48m

$559

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 10/16

9:35 am-3:49 pm

1 stop5h 14m

White Plains Westchester County

Sun 10/19

12:55 pm-6:25 pm

1 stop6h 30m

$589

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 33 results
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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 August 8, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to White Plains, you should look to book at least 73 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 August 14, 2025.

It’s typically best to fly out from Chicago to White Plains in the morning. Doing so could potentially save you 11% 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 August 14, 2025.

The most flights from CHI to HPN are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 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 August 14, 2025.
Peruse reviews from past customers who have flown with Delta, American Airlines, and Spirit 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
7,980 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

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
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

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
7,980 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
Spirit Airlines
6.3
Okay
8,045 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

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.

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

    According to our current data, American Airlines ($349), 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 (80%), American Airlines (72%), Envoy Air( 72%).

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

    On average you can expect to pay $496 for a flight from Chicago to White Plains. The cheapest flight overall is $263 while the most popular route, (Chicago O'Hare Intl - White Plains Westchester County) is currently priced at $359.

  • 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$349Average$454FlexibilityNo cancel feeOn-time71%

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