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White Plains

$95+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Mar 23 — Mar 301
Mon 3/23
Mon 3/30
1 adult, Economy
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Cheap 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 February 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Fri 5/81:27 pm
ORD
-
HPN
2 stops20h 50m
Multiple Airlines
Mon 5/116:09 pm
HPN
-
ORD
1 stop6h 07m
Multiple Airlines
Deal found 2/18$253
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:27 pm
ORD
-
HPN
2 stops20h 50m
Multiple Airlines
Sun 5/108:00 am
HPN
-
ORD
1 stop16h 16m
Multiple Airlines
Deal found 2/19$293
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/256:38 pm
ORD
-
HPN
Nonstop2h 21m
American Airlines
Sat 3/284:30 pm
HPN
-
ORD
Nonstop2h 48m
American Airlines
Deal found 2/20$355
This Delta deal was found by Cheapflights users on 2/20. 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 12/11:15 pm
ORD
-
HPN
1 stop7h 21m
Delta
Sat 12/512:45 pm
HPN
-
ORD
1 stop4h 52m
Delta
Deal found 2/20$375
This Delta deal was found by Cheapflights users on 2/20. 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 4/146:00 am
MDW
-
HPN
1 stop5h 00m
Delta
Tue 4/2112:30 pm
HPN
-
MDW
1 stop6h 28m
Delta
Deal found 2/20$375
This American Airlines deal was found by Cheapflights users on 2/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/18:09 am
ORD
-
HPN
Nonstop2h 20m
American Airlines
Wed 8/512:00 pm
HPN
-
ORD
Nonstop2h 36m
American Airlines
Deal found 2/17$385
This American Airlines deal was found by Cheapflights users on 2/20. 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 6/512:37 pm
ORD
-
HPN
Nonstop2h 17m
American Airlines
Tue 6/97:10 am
HPN
-
ORD
Nonstop2h 41m
American Airlines
Deal found 2/20$389
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/306:15 am
ORD
-
HPN
1 stop9h 22m
Delta
Tue 4/73:13 pm
HPN
-
ORD
1 stop5h 36m
Delta
Deal found 2/19$390
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1212:34 pm
ORD
-
HPN
1 stop21h 54m
Multiple Airlines
Sun 3/1512:08 pm
HPN
-
ORD
2 stops12h 30m
Multiple Airlines
Deal found 2/17$394
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
MDW
-
HPN
1 stop5h 14m
Delta
Wed 8/512:45 pm
HPN
-
MDW
1 stop6h 46m
Delta
Deal found 2/19$405
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:30 am
MDW
-
HPN
1 stop6h 59m
Delta
Tue 6/912:45 pm
HPN
-
MDW
1 stop6h 46m
Delta
Deal found 2/19$409
This Delta deal was found by Cheapflights users on 2/18. 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 3/39:50 am
MDW
-
HPN
1 stop5h 42m
Delta
Sat 3/75:12 pm
HPN
-
MDW
1 stop6h 19m
Delta
Deal found 2/18$435

Find 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 February 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$253
(Kiwi.com)

One-way from

$95
(Kiwi.com)

Popular in

January

Cheapest in

December

Average price

$479

Good round-trip deal

$389 or less

Good one-way deal

$289 or less
Provider with most accurate pricing for Chicago (CHI)-White Plains Westchester County flight deals.
Search Deals
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. 2% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 21, 2026.
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 3/25

1:38 pm-4:47 pm

Nonstop2h 09m

White Plains Westchester County

Sat 3/28

4:30 pm-6:18 pm

Nonstop2h 48m

$355

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 3/21

7:10 am-11:43 am

1 stop3h 33m

White Plains Westchester County

Tue 3/24

12:35 pm-4:43 pm

1 stop5h 08m

$375

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 8/15

9:30 am-6:13 pm

1 stop7h 43m

White Plains Westchester County

Sat 8/22

4:19 pm-11:57 pm

1 stop8h 38m

$375

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 8/1

10:35 am-4:33 pm

1 stop4h 58m

White Plains Westchester County

Wed 8/5

12:45 pm-6:41 pm

1 stop6h 56m

$375

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 4/15

6:00 am-12:00 pm

1 stop5h 00m

White Plains Westchester County

Tue 4/21

12:30 pm-5:58 pm

1 stop6h 28m

$375

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 3/21

8:14 am-11:29 am

Nonstop2h 15m

White Plains Westchester County

Sun 3/22

4:30 pm-6:18 pm

Nonstop2h 48m

$389

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 8/1

8:09 am-11:29 am

Nonstop2h 20m

White Plains Westchester County

Wed 8/5

6:30 am-12:12 pm

1 stop6h 42m

$395

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 4/1

6:08 am-10:59 am

1 stop3h 51m

White Plains Westchester County

Sun 4/5

12:00 pm-1:43 pm

Nonstop2h 43m

$399

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 3/25

9:50 am-3:49 pm

1 stop4h 59m

White Plains Westchester County

Sat 3/28

12:35 pm-4:18 pm

1 stop4h 43m

$405

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Sat 8/1

6:00 am-12:14 pm

1 stop5h 14m

White Plains Westchester County

Wed 8/5

12:45 pm-6:31 pm

1 stop6h 46m

$405

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/17

Showing 1-10 of 32 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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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

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 $34). Flying from Chicago to White Plains in July is currently the most expensive (average of $103). 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 February 21, 2026.

It’s typically best to fly out from Chicago to White Plains in the morning. Doing so could potentially save you 5% on the flight price compared to flying in the evening, which is usually more expensive.

What is the cheapest day to fly from Chicago to White Plains?

Use this chart to determine the cheapest time to fly round-trip from Chicago to White Plains. Price data was last updated on February 17, 2026.

Travelers seeking maximum savings on their Chicago to White Plains flight should consider departing on Sunday at noon when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 February 21, 2026.

The most flights from CHI to HPN are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, 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 February 21, 2026.
Peruse reviews from past customers who have flown with 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.
American Airlines
7.2
Good
11,334 reviews

Comfort

7.2

Crew

8.0

Boarding

7.5

Overall

7.2

Food

6.4

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Adwitiya,Sep 2025

DEL - JFK

I recently flew AA’s business class from Delhi to New York, and while the experience ticked the basic boxes, it didn’t quite soar. - Dining: I opted for the vegetarian meal, which was… fine. Not memorable, not offensive—just hovering in the realm of “meh.” The menu could use a refresh with more thoughtful, flavorful options. - Seating: AA seems to be chasing quantity over quality, squeezing in as many business class seats as possible. Yes, they’re lie-flat, but noticeably narrower than what you’d find on other international carriers. Comfort was passable, but not premium. Overall, I’d call it “business class lite.” It gets the job done, but lacks the finesse and attention to detail that elevate a journey. A few strategic tweaks—better food, more spacious seating, and a touch more hospitality—could make a world of difference.
American Airlines
7.2
Good
11,334 reviews
American Airlines
7.2
Good
11,334 reviews

Comfort

7.2

Crew

8.0

Boarding

7.5

Overall

7.2

Food

6.4

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Adwitiya,Sep 2025

DEL - JFK

I recently flew AA’s business class from Delhi to New York, and while the experience ticked the basic boxes, it didn’t quite soar. - Dining: I opted for the vegetarian meal, which was… fine. Not memorable, not offensive—just hovering in the realm of “meh.” The menu could use a refresh with more thoughtful, flavorful options. - Seating: AA seems to be chasing quantity over quality, squeezing in as many business class seats as possible. Yes, they’re lie-flat, but noticeably narrower than what you’d find on other international carriers. Comfort was passable, but not premium. Overall, I’d call it “business class lite.” It gets the job done, but lacks the finesse and attention to detail that elevate a journey. A few strategic tweaks—better food, more spacious seating, and a touch more hospitality—could make a world of difference.

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 2h 09m. The time it takes to get you to your destination can typically vary by up to 1h 24m. 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 ($375), 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 (73%), American Airlines (64%), Envoy Air( 64%).

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

    On average you can expect to pay $431 for a flight from Chicago to White Plains. The cheapest flight overall is $243 while the most popular route, (Chicago O'Hare Intl - White Plains Westchester County) is currently priced at $375.

  • 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 $34). Flying from Chicago to White Plains in July is currently the most expensive (average of $103). 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 February 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$375Average$480FlexibilityNo cancel feeOn-time71%

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