HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
White Plains

$81+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to White Plains with Cheapflights

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”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 6, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$265
(Kiwi.com)

One-way from

$81
(Kiwi.com)

Popular in

November

Cheapest in

December

Average price

$435

Good round-trip deal

$436 or less

Good one-way deal

$303 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 ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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

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 January 6, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/4. 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.
Mon 2/169:41 pmORD - HPN
2 stops12h 47mMultiple Airlines
Mon 2/2312:08 pmHPN - ORD
1 stop12h 29mMultiple Airlines
Deal found 1/4$265
This American Airlines deal was found by Cheapflights users on 1/6. 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 1/2810:05 amORD - HPN
1 stop11h 54mAmerican Airlines
Tue 2/107:00 amHPN - ORD
1 stop12h 10mAmerican Airlines
Deal found 1/6$285
This Kiwi.com deal was found by Cheapflights users on 1/4. 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 4/92:00 pmORD - HPN
1 stop20h 28mMultiple Airlines
Mon 4/1312:08 pmHPN - ORD
2 stops29h 39mMultiple Airlines
Deal found 1/4$327
This American Airlines deal was found by Cheapflights users on 1/4. 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 3/286:38 pmORD - HPN
Nonstop2h 21mAmerican Airlines
Wed 4/15:29 pmHPN - ORD
Nonstop2h 48mAmerican Airlines
Deal found 1/4$349
This Delta deal was found by Cheapflights users on 1/6. 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 1/2711:15 amORD - HPN
1 stop9h 45mDelta
Sat 2/75:15 pmHPN - ORD
1 stop7h 41mDelta
Deal found 1/6$356
This Delta deal was found by Cheapflights users on 1/6. 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 1/275:30 amORD - HPN
1 stop11h 30mDelta
Mon 2/96:40 pmHPN - ORD
1 stop15h 02mDelta
Deal found 1/6$357
This Delta deal was found by Cheapflights users on 1/6. 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 1/315:30 amORD - HPN
1 stop5h 36mDelta
Wed 2/1112:38 pmHPN - ORD
1 stop9h 27mDelta
Deal found 1/6$367
This Delta deal was found by Cheapflights users on 1/4. 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 3/287:10 amORD - HPN
1 stop3h 33mDelta
Wed 4/13:13 pmHPN - ORD
1 stop5h 36mDelta
Deal found 1/4$369
This Delta deal was found by Cheapflights users on 1/5. 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 3/149:35 amORD - HPN
1 stop6h 00mDelta
Mon 3/165:17 pmHPN - ORD
1 stop21h 00mDelta
Deal found 1/5$376
This Delta deal was found by Cheapflights users on 1/5. 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 3/310:49 amMDW - HPN
1 stop6h 11mDelta
Thu 3/2612:48 pmHPN - MDW
1 stop5h 07mDelta
Deal found 1/5$400
This Delta deal was found by Cheapflights users on 1/4. 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 1/175:31 pmMDW - HPN
1 stop15h 17mDelta
Wed 2/254:29 pmHPN - MDW
1 stop7h 02mDelta
Deal found 1/4$401
This Delta deal was found by Cheapflights users on 1/6. 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 1/76:45 amMDW - HPN
1 stop6h 41mDelta
Wed 1/144:29 pmHPN - MDW
1 stop6h 38mDelta
Deal found 1/6$415

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 January 6, 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

Thu 1/29

9:55 am-10:00 pm

1 stop11h 05m

White Plains Westchester County

Wed 2/11

5:12 pm-9:05 pm

1 stop4h 53m

$356

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 1/27

9:55 am-10:00 pm

1 stop11h 05m

White Plains Westchester County

Wed 2/11

12:38 pm-4:57 pm

1 stop5h 19m

$356

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 1/27

5:30 am-6:00 pm

1 stop11h 30m

White Plains Westchester County

Mon 2/9

6:40 pm-8:42 am

1 stop15h 02m

$357

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 1/29

9:55 am-10:00 pm

1 stop11h 05m

White Plains Westchester County

Mon 2/9

12:59 pm-9:00 pm

1 stop9h 01m

$357

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 3/28

7:10 am-11:43 am

1 stop3h 33m

White Plains Westchester County

Wed 4/1

3:13 pm-7:49 pm

1 stop5h 36m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 1/31

6:50 am-11:56 am

1 stop4h 06m

White Plains Westchester County

Sat 2/7

12:38 pm-4:38 pm

1 stop5h 00m

$385

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 1/28

5:30 am-6:00 pm

1 stop11h 30m

White Plains Westchester County

Fri 2/13

12:36 pm-4:41 pm

1 stop5h 05m

$390

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 1/29

9:55 am-10:00 pm

1 stop11h 05m

White Plains Westchester County

Sun 2/8

12:38 pm-4:28 pm

1 stop4h 50m

$390

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 3/4

5:25 am-12:06 pm

1 stop5h 41m

White Plains Westchester County

Thu 3/26

3:13 pm-7:49 pm

1 stop5h 36m

$400

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

Sun 3/22

5:17 pm-8:14 pm

1 stop3h 57m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

Showing 1-10 of 43 results
1
2
3
...
5

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 January.
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 $34). 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 January 6, 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 January 3, 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 January 6, 2026.

The most flights from CHI to HPN are scheduled on a Monday (6 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (3 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 January 6, 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
11,083 reviews

Overall

7.2

Entertainment

6.9

Comfort

7.2

Food

6.4

Boarding

7.5

Crew

8.0

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
11,083 reviews
American Airlines
7.2
Good
11,083 reviews

Overall

7.2

Entertainment

6.9

Comfort

7.2

Food

6.4

Boarding

7.5

Crew

8.0

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 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 11h 05m. The time it takes to get you to your destination can typically vary by up to . There are 736 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 16% 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 (74%), American Airlines (68%), Envoy Air( 68%).

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

    On average you can expect to pay $465 for a flight from Chicago to White Plains. The cheapest flight overall is $245 while the most popular route, (Chicago O'Hare Intl - White Plains Westchester County) is currently priced at $265.

  • 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 $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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to White Plains

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
Midway to LaGuardia flights
Midway to John F Kennedy Intl flights
St. Louis to LaGuardia flights
St. Louis to Newark flights
Midway to Newark flights
St. Louis to John F Kennedy Intl flights
O'Hare Intl to Buffalo flights
O'Hare Intl to Syracuse flights
O'Hare Intl to Rochester flights
Moline to John F Kennedy Intl flights
O'Hare Intl to Albany flights
Moline to LaGuardia flights
O'Hare Intl to White Plains flights
Moline to Newark flights
Midway to Syracuse flights
Midway to Buffalo flights
Peoria to Newark flights
Peoria to John F Kennedy Intl flights
St. Louis to Buffalo flights
O'Hare Intl to Islip flights
Peoria to LaGuardia flights
St. Louis to Albany flights
Midway to Albany flights
O'Hare Intl to Rutland flights
Midway to Rochester flights
Midway to White Plains flights
St. Louis to Rochester flights
Evansville to Newark flights
Bloomington to LaGuardia flights
St. Louis to Syracuse flights
O'Hare Intl to Ithaca flights
Evansville to LaGuardia flights
Evansville to John F Kennedy Intl flights
Bloomington to John F Kennedy Intl flights
O'Hare Intl to Stewart flights
Moline to Rochester flights
Bloomington to Newark flights
Champaign to LaGuardia flights
Champaign to John F Kennedy Intl flights
Moline to Buffalo flights
St. Louis to White Plains flights
Champaign to Newark flights
Peoria to Buffalo flights
Springfield to LaGuardia flights
Moline to Albany flights
Dubuque to Rochester flights

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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$375Average$476FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.