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$106+ Cheap flights from White Plains (HPN) to Chicago (CHI)

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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Mar 21 — Mar 281
Sat 3/21
Sat 3/28
1 adult, Economy
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Cheapflights Tip: The best prices from White Plains Westchester County to Chicago are usually found in January or September, booked 78 days in advance, depart on a Saturday or Tuesday and return on a Saturday

Cheap flight deals from White Plains to Chicago

Cheapest flights from White Plains to Chicago
Explore the most affordable flight options available from White Plains to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 19, 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.
Mon 5/116:09 pm
HPN
-
ORD
1 stop6h 07m
Multiple Airlines
Wed 5/131:40 pm
ORD
-
HPN
2 stops30h 19m
Multiple Airlines
Deal found 2/18$223
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 5/112:08 pm
HPN
-
ORD
1 stop12h 08m
Multiple Airlines
Sun 5/31:12 pm
ORD
-
HPN
1 stop21h 16m
Multiple Airlines
Deal found 2/15$262
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.
Tue 3/1012:08 pm
HPN
-
ORD
2 stops12h 30m
Multiple Airlines
Thu 3/1212:34 pm
ORD
-
HPN
1 stop21h 54m
Multiple Airlines
Deal found 2/17$265
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.
Mon 5/412:08 pm
HPN
-
ORD
1 stop11h 58m
Multiple Airlines
Wed 5/61:40 pm
ORD
-
HPN
2 stops30h 19m
Multiple Airlines
Deal found 2/18$268
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.
Tue 3/1712:08 pm
HPN
-
ORD
2 stops12h 30m
Multiple Airlines
Thu 3/1912:34 pm
ORD
-
HPN
1 stop21h 54m
Multiple Airlines
Deal found 2/18$280
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.
Tue 4/2112:08 pm
HPN
-
ORD
2 stops12h 02m
Multiple Airlines
Thu 4/231:12 pm
ORD
-
HPN
1 stop21h 16m
Multiple Airlines
Deal found 2/18$312
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.
Tue 4/1412:08 pm
HPN
-
ORD
2 stops20h 55m
Multiple Airlines
Thu 4/161:12 pm
ORD
-
HPN
1 stop21h 16m
Multiple Airlines
Deal found 2/17$314
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 4/1712:08 pm
HPN
-
ORD
1 stop12h 08m
Multiple Airlines
Mon 4/206:57 am
ORD
-
HPN
2 stops27h 31m
Multiple Airlines
Deal found 2/15$323
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 4/1712:08 pm
HPN
-
ORD
1 stop12h 08m
Multiple Airlines
Sun 4/1910:25 am
ORD
-
HPN
2 stops24h 03m
Multiple Airlines
Deal found 2/15$324
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 4/185:20 pm
HPN
-
MDW
1 stop6h 08m
Delta
Tue 4/216:00 am
MDW
-
HPN
1 stop7h 29m
Delta
Deal found 2/19$375
This Delta deal was found by Cheapflights users on 2/15. 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 4/176:54 pm
HPN
-
MDW
1 stop16h 02m
Delta
Sun 4/199:27 am
MDW
-
HPN
1 stop5h 22m
Delta
Deal found 2/15$380
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/145:15 pm
HPN
-
MDW
1 stop6h 16m
Delta
Sat 3/219:30 am
MDW
-
HPN
1 stop6h 05m
Delta
Deal found 2/17$405

Find flight deals from White Plains to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from White Plains (HPN) to Chicago (CHI). 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 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$223
(Kiwi.com)

One-way from

$106
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$483

Good round-trip deal

$336 or less

Good one-way deal

$250 or less
Provider with most accurate pricing for White Plains Westchester County-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for White Plains Westchester County-Chicago (CHI) flights.
Search Deals
From White Plains Westchester County to Chicago (CHI)
Search Deals
One-way flight from White Plains Westchester County to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 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 White Plains Westchester County to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from White Plains Westchester County to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from White Plains to Chicago 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 19, 2026.
Use the filters below to find and compare flights from White Plains to Chicago that are best for you.

Fly from

White Plains

Fly to

Chicago

Route

Depart

Return

Price

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Mon 3/23

1:10 pm-11:50 am

2 stops23h 40m

Chicago O'Hare Intl

Sun 3/29

12:34 pm-11:28 am

1 stop21h 54m

$333

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Mon 4/20

12:08 pm-11:06 pm

1 stop11h 58m

Chicago O'Hare Intl

Thu 4/23

1:12 pm-11:28 am

1 stop21h 16m

$335

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 7/21

12:45 pm-6:31 pm

1 stop6h 46m

Chicago Midway

Tue 7/28

9:30 am-4:33 pm

1 stop6h 03m

$375

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 4/18

5:20 pm-10:28 pm

1 stop6h 08m

Chicago Midway

Tue 4/21

6:00 am-2:29 pm

1 stop7h 29m

$375

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 7/4

3:15 pm-9:34 pm

1 stop7h 19m

Chicago O'Hare Intl

Wed 7/8

7:10 am-11:44 am

1 stop3h 34m

$375

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 7/25

12:45 pm-4:36 pm

1 stop4h 51m

Chicago O'Hare Intl

Sat 8/1

7:10 am-11:44 am

1 stop3h 34m

$375

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 6/27

5:10 pm-8:24 pm

1 stop4h 14m

Chicago O'Hare Intl

Sat 7/4

12:10 pm-9:41 pm

1 stop8h 31m

$375

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 4/17

6:54 pm-9:56 am

1 stop16h 02m

Chicago Midway

Sun 4/19

9:27 am-3:49 pm

1 stop5h 22m

$380

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 4/17

6:54 pm-8:37 am

1 stop14h 43m

Chicago O'Hare Intl

Sun 4/19

11:00 am-3:49 pm

1 stop3h 49m

$380

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 3/3

11:28 am-3:17 pm

1 stop4h 49m

Chicago O'Hare Intl

Sat 3/21

1:38 pm-4:47 pm

Nonstop2h 09m

$395

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/17

Showing 1-10 of 44 results
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Compare providers for flights from White Plains to Chicago

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 White Plains to Chicago 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 White Plains-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on White Plains-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from White Plains-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on White Plains-Chicago 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 White Plains-Chicago 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 White Plains to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from White Plains 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 White Plains to Chicago

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

Use this chart to determine the optimal time to book a round-trip flight from White Plains to Chicago. Price data was last updated on February 18, 2026.

The best time to book flights from White Plains to Chicago is 78 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from White Plains to Chicago?

Currently, December is the cheapest month in which you can book a flight from White Plains to Chicago (average of $48). Flying from White Plains to Chicago in July is currently the most expensive (average of $119). 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 HPN to CHI?

Find hourly flight availability from White Plains to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 19, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from White Plains to Chicago as you normally would.

Weekly flight availability from White Plains to Chicago

Explore weekly flight availability from White Plains to Chicago. 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 19, 2026.

The most flights from HPN to CHI 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).

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated February 19, 2026.
Peruse reviews from past customers who have flown with Delta and American Airlines from White Plains to Chicago 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
7.9
Good
8,215 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
7.9
Good
8,215 reviews
Delta
7.9
Good
8,215 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
11,321 reviews
Delta
7.9
Good
8,215 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

Related info for your journey

Find useful and relevant information for your journey from White Plains to Chicago. 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 from for flights from White Plains to Chicago?

    Most people fly from White Plains Westchester County (HPN) if they book a flight from White Plains to Chicago. On average, Westchester County has 7 outbound flights to Chicago per day from 1 airline. White Plains Westchester County is conveniently located just 3.7 mi from White Plains’s city center.

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

    Delta can get you from White Plains to Chicago in just under 6h 46m. Your travel time can differ by up to . The distance between White Plains and Chicago is about 728 mi.

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

    Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $370. Users have found that American Airlines is 22% cheaper than the other options available to this destination.

  • What are the most reliable airlines from White Plains to Chicago?

    Before booking your flight to Chicago from White Plains, check out the most reliable airlines to get you to your destination on time: American Airlines (85%), Envoy Air (85%), Alaska Airlines( 76%).

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

    The cheapest flight price from White Plains to Chicago is $156. On average you can expect to pay $585. The most popular route, (White Plains Westchester County - Chicago O'Hare Intl), can usually be booked for $223.

  • Can I find deals for flights from White Plains to Chicago that include hotel bookings?

    Yes. In addition to deals on White Plains to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from White Plains to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from White Plains to Chicago.

  • Can I find deals for business class flights from White Plains to Chicago?

    Yes. Cheapflights offers flight deals from White Plains to Chicago 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 White Plains to Chicago?

    Currently, December is the cheapest month in which you can book a flight from White Plains to Chicago (average of $48). Flying from White Plains to Chicago in July is currently the most expensive (average of $119). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for White Plains to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from White Plains to Chicago

Discover the top airline that operate flights from White Plains to Chicago. 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 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$370Average$483FlexibilityNo cancel feeOn-time71%

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