What are the cheapest airlines flying from White Plains to Chicago round-trip?

Flying on Delta is currently your cheapest option to Chicago, with prices starting at $333. Another option worth looking into is American Airlines, starting at $349 round trip. Users have found that Delta is 27% cheaper than the other options available to this destination.

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

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

What are the cheapest flights from White Plains to Chicago?

The cheapest flight price from White Plains to Chicago is $120. On average you can expect to pay $769. The most popular route, (White Plains Westchester County - Chicago O'Hare Intl), can usually be booked for $261.

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: Qatar Airways (79%), American Airlines (78%), Envoy Air( 78%).

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

Users have found that flying from White Plains to Chicago on a Sunday typically leans towards higher prices. However, this doesn’t mean you still can’t find a deal. Flexibility with other aspects of your flight can still land a great price for your trip.

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

Travelers have found it’s best to book a flight 31 days in advance to save up to 88% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 31 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from White Plains to Chicago 1-2 weeks in advance for as low as $211, or $359 for flights within the next 24 hours.

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

September can be a great time to fly to Chicago from White Plains with a flight ticket averaging about $226. Cheapflights users have found deals in the month of September for as cheap as $74. The most expensive prices can be found in the month of December.

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.

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 3 outbound flights to Chicago per day from 2 airlines. White Plains Westchester County is conveniently located just 3.7 mi from White Plains’s city center.

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.

$182+ Flights from White Plains to Chicago

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1. Tell us where you want to go

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3. Compare prices and book

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Cheapflights Tip: The best prices from White Plains Westchester County to Chicago are usually found in July or September, booked 57 days in advance, depart on a Wednesday or Saturday and return on a Saturday

Cheap flight deals from White Plains to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$333 (Delta)
One-way from	$182 (Delta)
Popular in	June
Cheapest in	July
Average price	$451
Good round-trip deal	$376 or less
Good one-way deal	$148 or less

Provider with most accurate pricing for White Plains Westchester County-Chicago (CHI) flight deals.

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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. 3% potential increase in price ($16 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 March 2025

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Price to beat on a round-trip flight from White Plains Westchester County to Chicago (CHI).

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Price to beat on a one-way flight from White Plains Westchester County to Chicago (CHI).

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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 March 27, 2025.

Fri 4/185:15 pmHPN - ORD

1 stop17h 09mDelta

Fri 4/256:15 pmORD - HPN

1 stop16h 35mDelta

Deal found 3/25

$333

Tue 5/206:00 amHPN - ORD

Nonstop2h 30mAmerican Airlines

Sat 5/248:22 amORD - HPN

Nonstop2h 07mAmerican Airlines

Deal found 3/26

$349

Tue 5/204:29 pmHPN - MDW

1 stop5h 58mDelta

Sat 5/249:20 amMDW - HPN

1 stop6h 10mDelta

Deal found 3/25

$369

Fri 5/1612:06 pmHPN - ORD

2 stops12h 23mMultiple Airlines

Sun 5/184:35 pmORD - HPN

2 stops17h 46mMultiple Airlines

Deal found 3/26

$524

Best flights from White Plains to Chicago
Discover carefully curated flight deals from White Plains to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 27, 2025.

Fri 4/185:15 pmHPN - ORD

1 stop17h 09mDelta

Fri 4/256:15 pmORD - HPN

1 stop16h 35mDelta

Deal found 3/25

$333

Tue 5/206:00 amHPN - ORD

Nonstop2h 30mAmerican Airlines

Sat 5/248:22 amORD - HPN

Nonstop2h 07mAmerican Airlines

Deal found 3/26

$349

Fri 5/1612:06 pmHPN - ORD

2 stops12h 23mMultiple Airlines

Sun 5/184:35 pmORD - HPN

2 stops17h 46mMultiple Airlines

Deal found 3/26

$524

Tue 5/204:29 pmHPN - MDW

1 stop5h 58mDelta

Sat 5/249:20 amMDW - HPN

1 stop6h 10mDelta

Deal found 3/25

$369

Last-minute flights from White Plains to Chicago
Discover last-minute flight deals from White Plains to Chicago. Data last updated March 27, 2025 and is based on user searches.

Tue 4/112:35 pmHPN - MDW

1 stop6h 27mDelta

Tue 4/89:23 amMDW - HPN

1 stop6h 17mDelta

Deal found 3/26

$439

Tue 4/18:20 amHPN - ORD

3 stops38h 12mMultiple Airlines

Thu 4/39:08 pmORD - HPN

2 stops14h 22mMultiple Airlines

Deal found 3/25

$576

Wed 4/27:15 amHPN - ORD

Nonstop2h 34mAmerican Airlines

Wed 4/212:50 pmORD - HPN

Nonstop2h 09mAmerican Airlines

Deal found 3/26

$411

Wed 4/26:00 amHPN - ORD

1 stop5h 06mDelta

Wed 4/22:55 pmORD - HPN

1 stop6h 20mDelta

Deal found 3/26

$431

Fri 4/185:15 pmHPN - ORD

1 stop17h 09mDelta

Fri 4/256:15 pmORD - HPN

1 stop16h 35mDelta

Deal found 3/25

$333

Tue 4/221:29 pmHPN - ORD

2 stops29h 48mMultiple Airlines

Tue 4/295:36 amORD - HPN

2 stops29h 54mMultiple Airlines

Deal found 3/25

$532

Thu 4/247:15 amHPN - ORD

Nonstop2h 36mAmerican Airlines

Sat 4/266:31 pmORD - HPN

Nonstop2h 22mAmerican Airlines

Deal found 3/25

$375

Thu 4/2412:32 pmHPN - MDW

1 stop6h 48mDelta

Sat 4/269:20 amMDW - HPN

1 stop6h 28mDelta

Deal found 3/25

$395

One-way flights from White Plains to Chicago
Search for one-way flight options from White Plains to Chicago. Find affordable one-way fares based on user searches. Data last updated March 27, 2025.

Thu 4/246:00 amHPN - ORD

1 stop18h 59mDelta

Deal found 3/25

$182

Sat 5/36:30 amHPN - ORD

2 stops11h 15mAmerican Airlines

Deal found 3/25

$199

Tue 7/296:00 amHPN - MDW

1 stop4h 51mDelta

Deal found 3/25

$210

Mon 3/319:20 amHPN - ORD

2 stops28h 25mMultiple Airlines

Deal found 3/25

$292

Cheapflights Fare Finder

Use the filters below to find and compare flights from White Plains to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 4/18

5:15 pm-8:19 am

1 stop16h 04m

Chicago O'Hare Intl

Sat 4/26

6:45 am-4:48 pm

1 stop9h 03m

$333

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 5/20

6:00 am-7:30 am

Nonstop2h 30m

Chicago O'Hare Intl

Sat 5/24

8:22 am-11:29 am

Nonstop2h 07m

$349

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 5/20

4:29 pm-9:27 pm

1 stop5h 58m

Chicago Midway

Sat 5/24

9:20 am-4:30 pm

1 stop6h 10m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 5/16

12:06 pm-11:29 pm

2 stops12h 23m

Chicago O'Hare Intl

Sun 5/18

4:35 pm-11:21 am

2 stops17h 46m

$524

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 4/24

6:00 am-11:59 pm

1 stop18h 59m

$182

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 5/3

6:30 am-4:45 pm

2 stops11h 15m

$199

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 7/29

6:00 am-9:51 am

1 stop4h 51m

$210

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Mon 3/31

9:20 am-11:27 am

2 stops27h 07m

$292

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Compare providers for flights from White Plains to Chicago

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 March.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Priceline	Price Accuracy1 star	Trust 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?

The best time to book flights from White Plains to Chicago is 57 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 $323). 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?

It’s optimal to fly from White Plains to Chicago in the afternoon. By choosing this option you can save up to 69% on the cost of your flight, compared to a flight in the morning.

Weekly flight availability from White Plains to Chicago

The most flights from HPN to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Chicago by month

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Delta and American Airlines from White Plains to Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,895 reviews

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

7,895 reviews

Delta

8.0

Very good

7,895 reviews

Reviews

1 / 20

10.0

Excellent

Kymberlee,Oct 2024

JFK - ATL

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,895 reviews

Reviews

1 / 20

10.0

Excellent

Kymberlee,Oct 2024

JFK - ATL

Related info for your journey

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 3 outbound flights to Chicago per day from 2 airlines. White Plains Westchester County is conveniently located just 3.7 mi from White Plains’s city center.
What are the cheapest airlines flying from White Plains to Chicago round-trip?
Flying on Delta is currently your cheapest option to Chicago, with prices starting at $333. Another option worth looking into is American Airlines, starting at $349 round trip. Users have found that Delta is 27% 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: Qatar Airways (79%), American Airlines (78%), Envoy Air( 78%).
What are the cheapest flights from White Plains to Chicago?
The cheapest flight price from White Plains to Chicago is $120. On average you can expect to pay $769. The most popular route, (White Plains Westchester County - Chicago O'Hare Intl), can usually be booked for $261.
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 $323). 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

Merrillville

New Buffalo

Hammond

Benton Harbor

Porter

Lansing

Valparaiso

Chesterton

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Top 2 airlines flying from White Plains to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$148	Average$387	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$319	Average$467	FlexibilityNo cancel fee	On-time71%

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$182+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from White Plains to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from White Plains Westchester County to Chicago are usually found in July or September, booked 57 days in advance, depart on a Wednesday or Saturday and return on a Saturday

Cheap flight deals from White Plains to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from White Plains to Chicago

Cheapest flights from White Plains to ChicagoExplore 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 March 27, 2025.

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 March 27, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from White Plains to Chicago that are best for you.

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 March.

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.

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 March 21, 2025.

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

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 March 27, 2025.

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 March 27, 2025.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Delta and American Airlines from White Plains to Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

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?

What are the cheapest airlines flying from White Plains to Chicago round-trip?

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

What are the cheapest flights from White Plains to Chicago?

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

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

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

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

Traveling to a place near White Plains?

Browse thousands of different options on Cheapflights for your next trip

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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.

Top 2 airlines flying from White Plains to Chicago

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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 March 27, 2025.