HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$147+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from White Plains to Chicago 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.

Cheapflights Tip: The best prices from White Plains Westchester County to Chicago are usually found in September or November, booked 28 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

Cheap 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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$349
(American Airlines)

One-way from

$147
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$401

Good round-trip deal

$376 or less

Good one-way deal

$256 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. 2% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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

Find 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 September 29, 2025.

This American Airlines deal was found by Cheapflights users on 9/28. 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 10/287:20 amHPN - ORD
Nonstop2h 36mAmerican Airlines
Tue 11/48:10 pmORD - HPN
Nonstop2h 19mAmerican Airlines
Deal found 9/28$349
This American Airlines deal was found by Cheapflights users on 9/28. 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 10/253:00 pmHPN - ORD
2 stops20h 43mAmerican Airlines
Sun 10/262:09 pmORD - HPN
Nonstop2h 18mAmerican Airlines
Deal found 9/28$364
This Kiwi.com deal was found by Cheapflights users on 9/27. 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.
Sun 11/168:00 amHPN - ORD
2 stops27h 41mMultiple Airlines
Thu 11/2010:00 amORD - HPN
1 stop24h 28mMultiple Airlines
Deal found 9/27$366
This Delta deal was found by Cheapflights users on 9/28. 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 10/2812:55 pmHPN - ORD
1 stop4h 16mDelta
Tue 11/45:20 amORD - HPN
1 stop8h 09mDelta
Deal found 9/28$369
This American Airlines deal was found by Cheapflights users on 9/29. 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 10/316:00 amHPN - ORD
Nonstop2h 36mAmerican Airlines
Sun 11/28:21 amORD - HPN
Nonstop2h 08mAmerican Airlines
Deal found 9/29$380
This American Airlines deal was found by Cheapflights users on 9/29. 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 10/285:57 pmHPN - ORD
Nonstop2h 41mAmerican Airlines
Wed 11/1212:48 pmORD - HPN
Nonstop2h 11mAmerican Airlines
Deal found 9/29$384
This American Airlines deal was found by Cheapflights users on 9/28. 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 11/266:00 amHPN - ORD
Nonstop2h 44mAmerican Airlines
Sat 11/298:10 pmORD - HPN
Nonstop2h 19mAmerican Airlines
Deal found 9/28$389
This American Airlines deal was found by Cheapflights users on 9/27. 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 11/256:30 amHPN - ORD
1 stop5h 28mAmerican Airlines
Sat 11/298:10 pmORD - HPN
Nonstop2h 19mAmerican Airlines
Deal found 9/27$399
This Delta deal was found by Cheapflights users on 9/28. 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 12/36:40 pmHPN - MDW
1 stop6h 09mDelta
Sun 12/79:34 amMDW - HPN
1 stop5h 15mDelta
Deal found 9/28$400
This Delta deal was found by Cheapflights users on 9/29. 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 10/3112:45 pmHPN - ORD
1 stop7h 04mDelta
Sun 11/28:57 amORD - HPN
1 stop6h 41mDelta
Deal found 9/29$400
This Delta deal was found by Cheapflights users on 9/28. 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 10/2512:55 pmHPN - MDW
1 stop6h 30mDelta
Tue 10/2810:35 amMDW - HPN
1 stop6h 25mDelta
Deal found 9/28$404
This Delta deal was found by Cheapflights users on 9/29. 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 11/136:00 amHPN - MDW
1 stop6h 52mDelta
Sun 11/169:41 amMDW - HPN
1 stop5h 53mDelta
Deal found 9/29$431

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 September 29, 2025.
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 - MDW

HPNMDW

White Plains Westchester County

Wed 12/3

6:40 pm-11:49 pm

1 stop6h 09m

Chicago Midway

Sun 12/7

9:34 am-3:49 pm

1 stop5h 15m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 12/5

10:27 am-4:18 pm

1 stop6h 51m

Chicago Midway

Wed 12/10

9:34 am-3:49 pm

1 stop5h 15m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 2/18

4:19 pm-9:46 pm

1 stop6h 27m

Chicago Midway

Sun 2/22

9:20 am-4:40 pm

1 stop6h 20m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 11/8

6:00 am-10:13 am

1 stop5h 13m

Chicago O'Hare Intl

Mon 11/10

8:55 am-3:49 pm

1 stop5h 54m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 10/31

12:45 pm-6:49 pm

1 stop7h 04m

Chicago O'Hare Intl

Sun 11/2

8:57 am-4:38 pm

1 stop6h 41m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 11/15

6:00 am-10:17 am

1 stop5h 17m

Chicago O'Hare Intl

Thu 11/20

5:23 am-12:00 pm

1 stop5h 37m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 11/1

6:00 am-10:20 am

1 stop5h 20m

Chicago O'Hare Intl

Sun 11/2

5:20 am-12:00 pm

1 stop5h 40m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Mon 10/27

5:20 pm-8:23 pm

1 stop4h 03m

Chicago O'Hare Intl

Tue 11/4

10:30 am-3:49 pm

1 stop4h 19m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 12/5

12:45 pm-6:43 pm

1 stop6h 58m

Chicago O'Hare Intl

Wed 12/10

5:30 am-12:00 pm

1 stop5h 30m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 1/1

12:55 pm-5:26 pm

1 stop5h 31m

Chicago Midway

Sun 1/4

9:29 am-3:49 pm

1 stop5h 20m

$431

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/28

Showing 1-10 of 36 results
1
2
3
4

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 September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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 September 26, 2025.

The best time to book flights from White Plains to Chicago is 28 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, August is the cheapest month in which you can book a flight from White Plains to Chicago (average of $245). Flying from White Plains to Chicago in March is currently the most expensive (average of $321). 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 September 29, 2025.

It’s optimal to fly from White Plains to Chicago in the afternoon. By choosing this option you can save up to 68% on the cost of your flight, compared to a flight in the morning.

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 September 29, 2025.

The most flights from HPN to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).

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 September 29, 2025.
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
8.0
Very good
7,964 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

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
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

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
10,000 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

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 8 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 09m. 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 $349. Users have found that American Airlines is 25% 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: Sun Country Air (100%), American Airlines (83%), Envoy Air( 83%).

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

    The cheapest flight price from White Plains to Chicago is $128. On average you can expect to pay $824. The most popular route, (White Plains Westchester County - Chicago O'Hare Intl), can usually be booked for $263.

  • 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, August is the cheapest month in which you can book a flight from White Plains to Chicago (average of $245). Flying from White Plains to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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 White Plains to Chicago

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

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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$349Average$473FlexibilityNo 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.