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$127+ Cheap flights from Westchester County 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Westchester County to Chicago

Keep the following information in mind while searching for Westchester County to Chicago flight deals. Data was last updated September 17, 2025.

Round-trip from

$349
(American Airlines)

One-way from

$127
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$213
From Westchester County to Chicago (CHI)
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One-way flight from Westchester County to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Westchester County to Chicago

Cheapest flights from Westchester County to Chicago
Explore the most affordable flight options available from Westchester County to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/216:00 amHPN - ORD
Nonstop2h 36mAmerican Airlines
Sat 10/252:09 pmORD - HPN
Nonstop2h 18mAmerican Airlines
Deal found 9/15$349
This Delta deal was found by Cheapflights users on 9/17. 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.
Wed 11/55:20 pmHPN - MDW
1 stop16h 20mDelta
Sat 11/86:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 9/17$351
This Delta deal was found by Cheapflights users on 9/17. 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.
Tue 11/45:20 pmHPN - ORD
1 stop15h 30mDelta
Sat 11/87:10 amORD - HPN
1 stop3h 49mDelta
Deal found 9/17$351
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Thu 11/68:00 amHPN - ORD
2 stops16h 28mMultiple Airlines
Sun 11/91:50 pmORD - HPN
1 stop20h 38mMultiple Airlines
Deal found 9/17$361
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 9/298:25 amHPN - ORD
2 stops26h 53mMultiple Airlines
Thu 10/211:36 amORD - HPN
1 stop22h 52mMultiple Airlines
Deal found 9/16$364
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 10/11:14 pmHPN - ORD
1 stop28h 37mMultiple Airlines
Sun 10/511:36 amORD - HPN
1 stop22h 52mMultiple Airlines
Deal found 9/16$365
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 10/2112:55 pmHPN - MDW
1 stop6h 30mDelta
Sat 10/2511:10 amMDW - HPN
1 stop3h 39mDelta
Deal found 9/15$369
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 10/215:20 pmHPN - ORD
1 stop4h 03mDelta
Sat 10/255:20 amORD - HPN
1 stop5h 40mDelta
Deal found 9/15$369
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/38:25 amHPN - ORD
2 stops26h 52mMultiple Airlines
Sun 10/511:36 amORD - HPN
1 stop22h 52mMultiple Airlines
Deal found 9/16$378
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:30 pmHPN - ORD
Nonstop2h 41mAmerican Airlines
Sun 11/166:37 pmORD - HPN
Nonstop2h 22mAmerican Airlines
Deal found 9/15$380
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/28:00 amHPN - ORD
2 stops16h 39mMultiple Airlines
Sun 10/511:36 amORD - HPN
1 stop22h 52mMultiple Airlines
Deal found 9/16$381
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:30 pmHPN - ORD
Nonstop2h 41mAmerican Airlines
Mon 11/171:15 pmORD - HPN
1 stop3h 58mAmerican Airlines
Deal found 9/15$390

Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County 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 17, 2025.
Use the filters below to find and compare flights from Westchester County to Chicago that are best for you.

Fly from

Westchester County

Fly to

Chicago

Route

Depart

Return

Price

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 11/5

5:20 pm-8:40 am

1 stop16h 20m

Chicago Midway

Sat 11/8

6:00 am-12:00 pm

1 stop5h 00m

$351

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 10/21

12:55 pm-6:25 pm

1 stop6h 30m

Chicago Midway

Sat 10/25

11:10 am-3:49 pm

1 stop3h 39m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 11/4

12:55 pm-6:25 pm

1 stop6h 30m

Chicago Midway

Sat 11/8

6:00 am-12:00 pm

1 stop5h 00m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 12/3

12:55 pm-6:00 pm

1 stop6h 05m

Chicago Midway

Sun 12/7

9:59 am-4:37 pm

1 stop5h 38m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 10/25

4:29 pm-10:14 pm

1 stop6h 45m

Chicago Midway

Mon 10/27

9:35 am-3:49 pm

1 stop5h 14m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 11/22

4:29 pm-11:32 pm

1 stop8h 03m

Chicago Midway

Fri 11/28

6:00 am-11:59 am

1 stop4h 59m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Mon 10/27

12:55 pm-6:25 pm

1 stop6h 30m

Chicago Midway

Tue 11/4

9:35 am-3:49 pm

1 stop5h 14m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 11/8

5:20 pm-11:58 pm

1 stop7h 38m

Chicago O'Hare Intl

Mon 11/10

10:46 am-3:49 pm

1 stop4h 03m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 10/25

6:40 pm-11:58 pm

1 stop6h 18m

Chicago O'Hare Intl

Mon 11/17

6:45 am-12:07 pm

1 stop4h 22m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 10/25

12:45 pm-6:49 pm

1 stop7h 04m

Chicago O'Hare Intl

Mon 10/27

10:30 am-3:49 pm

1 stop4h 19m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 40 results
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Best time to book a flight from Westchester County to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Westchester County 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 Westchester County to Chicago

What is the cheapest month to book a flight from Westchester County to Chicago?

Currently, August is the cheapest month in which you can book a flight from Westchester County to Chicago (average of $245). Flying from Westchester County 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 REU to CHI?

Find hourly flight availability from Westchester County 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 17, 2025.

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

Weekly flight availability from Westchester County to Chicago

Explore weekly flight availability from Westchester County 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 17, 2025.

The most flights from zzREU to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 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 17, 2025.
See what other customers who have flown with Delta and American Airlines from Westchester County to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Boarding

8.2

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
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Boarding

8.2

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
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Boarding

8.2

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 Westchester County to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Westchester County to Chicago?

    A quick flight from Westchester County to Chicago can take about 16h 20m. Delta provides one of the quickest options available for as low as $351. There are 728 mi between Westchester County and Chicago.

  • What are the most reliable airlines from Westchester County to Chicago?

    Consider Sun Country Air (100%), American Airlines (83%) or Envoy Air (83%) when booking your flight. These represent the most reliable airlines when flying from Westchester County to Chicago.

  • What are the cheapest flights from Westchester County to Chicago?

    Looking for the cheapest flight from Westchester County to Chicago? While on average our users pay $409, our data indicates the cheapest price to be $143. The most popular route (White Plains Westchester County - Chicago O'Hare Intl), is priced around $269.

  • Can I find deals for flights from Westchester County to Chicago that include hotel bookings?

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

  • How can I find direct flights from Westchester County to Chicago?

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

  • Can I find deals for business class flights from Westchester County to Chicago?

    Yes. Cheapflights offers flight deals from Westchester County 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 Westchester County to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Westchester County to Chicago (average of $245). Flying from Westchester County 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

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Alternative routes for Westchester County to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Westchester County to Chicago

Discover the top 2 airlines that operate flights from Westchester County 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$96Average$421FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$349Average$470FlexibilityNo cancel feeOn-time71%

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