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$225+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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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 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 June 12, 2025.

Round-trip from

$369
(American Airlines)

One-way from

$242
(Mytrip)

Popular in

June

Cheapest in

July

Average price

$491

Good round-trip deal

$394 or less

Good one-way deal

$239 or less
From White Plains Westchester County to Chicago (CHI)
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One-way flight from White Plains Westchester County to Chicago (CHI)
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Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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 7/1211:29 amHPN - ORD
1 stop5h 23mAmerican Airlines
Tue 7/153:33 pmORD - HPN
1 stop6h 55mAmerican Airlines
Deal found 6/11$369
This Delta deal was found by Cheapflights users on 6/11. 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 9/106:50 pmHPN - ORD
2 stops13h 36mDelta
Sat 9/137:00 amORD - HPN
2 stops13h 38mDelta
Deal found 6/11$371
This Delta deal was found by Cheapflights users on 6/12. 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 7/253:03 pmHPN - MDW
1 stop7h 39mDelta
Sat 7/266:00 amMDW - HPN
1 stop5h 01mDelta
Deal found 6/12$383
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/128:25 amHPN - ORD
1 stop11h 54mMultiple Airlines
Sun 9/143:29 pmORD - HPN
2 stops28h 01mMultiple Airlines
Deal found 6/10$412

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 June 12, 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 - ORD

HPNORD

White Plains Westchester County

Sat 7/12

11:29 am-3:52 pm

1 stop5h 23m

Chicago O'Hare Intl

Tue 7/15

3:33 pm-11:28 pm

1 stop6h 55m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 9/10

6:50 pm-7:26 am

2 stops13h 36m

Chicago O'Hare Intl

Sat 9/13

7:00 am-9:38 pm

2 stops13h 38m

$371

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 7/25

3:03 pm-9:42 pm

1 stop7h 39m

Chicago Midway

Sat 7/26

6:00 am-12:01 pm

1 stop5h 01m

$383

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 9/12

8:25 am-7:19 pm

1 stop11h 54m

Chicago O'Hare Intl

Sun 9/14

3:29 pm-8:30 pm

2 stops28h 01m

$412

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sun 9/28

12:09 pm-2:15 pm

2 stops27h 06m

$225

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 7/30

4:23 pm-9:30 pm

1 stop6h 07m

$256

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 8/15

6:00 am-7:36 am

Nonstop2h 36m

$264

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 7/10

12:55 pm-6:40 pm

1 stop6h 45m

$275

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sun 6/29

12:05 pm-2:03 pm

3 stops26h 58m

$494

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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 June 9, 2025.

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 $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 June 12, 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 June 12, 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).

Rainfall in Chicago by month

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

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

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 June 12, 2025.
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
7,946 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.2

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
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.2

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
7,946 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.2

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.

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

    Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $369. Another option worth looking into is Delta, starting at $371 round trip. Users have found that American Airlines is 19% 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 (81%), Envoy Air (81%), Alaska Airlines( 79%).

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

    The cheapest flight price from White Plains to Chicago is $144. On average you can expect to pay $751. The most popular route, (White Plains Westchester County - Chicago O'Hare Intl), can usually be booked for $293.

  • 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 White Plains?

Book flights to White Plains if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$324Average$453FlexibilityNo cancel feeOn-time71%

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