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White Plains

Cheap flights from Chicago (CHI) to White Plains (HPN)

CHI — HPN
May 8 — May 151
Fri 5/8
Fri 5/15
1 adult, Economy
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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”

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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 April 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$265
(Kiwi.com)

One-way from

$114
(Kiwi.com)

Popular in

January

Cheapest in

December

Average price

$423

Good round-trip deal

$459 or less

Good one-way deal

$428 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. 1% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in April 2026
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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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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 April.
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 $93). 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 April 8, 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 afternoon, 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 April 4, 2026.

Travelers seeking maximum savings on their Chicago to White Plains flight should consider departing on Saturday afternoons 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.

How much does it cost to fly round-trip from Chicago to White Plains?

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 April 8, 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
7.1
Good
11,549 reviews

Overall

7.1

Entertainment

6.9

Boarding

7.5

Food

6.4

Crew

7.9

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,549 reviews
American Airlines
7.1
Good
11,549 reviews

Overall

7.1

Entertainment

6.9

Boarding

7.5

Food

6.4

Crew

7.9

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

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 5 daily inbound flights from Chicago from 1 airline.

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

    Airlines like Delta fly from Chicago to White Plains in about 6h 12m. The time it takes to get you to your destination can typically vary by up to . There are 728 mi between Chicago and White Plains.

  • 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: Qatar Airways (75%), American Airlines (74%), Envoy Air( 74%).

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

    On average you can expect to pay $474 for a flight from Chicago to White Plains. The cheapest flight overall is $336 while the most popular route, (Chicago O'Hare Intl - White Plains Westchester County) is currently priced at $270.

  • 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 $93). 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

Browse thousands of different options on Cheapflights for your next trip

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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 April 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$375Average$485FlexibilityNo cancel feeOn-time71%

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