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$84+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 11/276:00 amHPN - ORD
Nonstop2h 44mAmerican Airlines
Thu 11/272:10 pmORD - HPN
Nonstop2h 19mAmerican Airlines
Deal found 10/29$379
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Sun 12/214:30 pmHPN - ORD
Nonstop2h 52mAmerican Airlines
Sat 12/278:10 amORD - HPN
Nonstop2h 19mAmerican Airlines
Deal found 10/30$380
This Delta deal was found by Cheapflights users on 10/29. 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 12/116:10 amHPN - MDW
1 stop18h 37mDelta
Sat 12/136:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 10/29$381
This Delta deal was found by Cheapflights users on 10/29. 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 12/116:10 amHPN - ORD
1 stop18h 51mDelta
Sat 12/136:45 amORD - HPN
1 stop6h 43mDelta
Deal found 10/29$381
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/2712:09 pmHPN - ORD
2 stops11h 57mMultiple Airlines
Thu 12/47:40 amORD - HPN
1 stop26h 48mMultiple Airlines
Deal found 10/30$386
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/2412:00 pmHPN - ORD
Nonstop2h 43mAmerican Airlines
Wed 12/316:39 pmORD - HPN
Nonstop2h 20mAmerican Airlines
Deal found 10/28$399
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/1412:10 pmHPN - ORD
1 stop12h 18mMultiple Airlines
Tue 11/1810:00 amORD - HPN
2 stops25h 34mMultiple Airlines
Deal found 10/30$409
This American Airlines deal was found by Cheapflights users on 10/30. 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 12/55:59 pmHPN - ORD
Nonstop2h 50mAmerican Airlines
Sun 12/78:16 amORD - HPN
Nonstop2h 13mAmerican Airlines
Deal found 10/30$411
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1812:09 pmHPN - ORD
2 stops11h 57mMultiple Airlines
Thu 11/2010:00 amORD - HPN
1 stop24h 28mMultiple Airlines
Deal found 10/29$424
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/256:00 amHPN - ORD
Nonstop2h 44mAmerican Airlines
Mon 12/16:37 pmORD - HPN
Nonstop2h 22mAmerican Airlines
Deal found 10/29$430
This Delta deal was found by Cheapflights users on 10/29. 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 12/116:10 amHPN - MDW
1 stop6h 45mDelta
Sun 12/146:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 10/29$431
This Delta deal was found by Cheapflights users on 10/29. 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 10/313:15 pmHPN - MDW
1 stop7h 59mDelta
Mon 11/39:35 amMDW - HPN
1 stop5h 14mDelta
Deal found 10/29$471

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 October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$369
(Delta)

One-way from

$84
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$242
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
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From Westchester County to Chicago (CHI)
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One-way flight from Westchester County to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
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 October 2025
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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 October 30, 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

Tue 1/20

12:36 pm-5:55 pm

1 stop6h 19m

Chicago Midway

Sat 1/24

6:00 am-12:08 pm

1 stop5h 08m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 3/21

4:19 pm-11:54 pm

1 stop8h 35m

Chicago O'Hare Intl

Tue 3/24

7:00 am-11:50 am

1 stop3h 50m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 12/11

6:10 am-11:47 pm

1 stop18h 37m

Chicago Midway

Sat 12/13

6:00 am-12:00 pm

1 stop5h 00m

$381

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 12/11

6:10 am-12:01 am

1 stop18h 51m

Chicago O'Hare Intl

Sat 12/13

6:45 am-2:28 pm

1 stop6h 43m

$381

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 12/18

12:55 pm-6:00 pm

1 stop6h 05m

Chicago Midway

Mon 12/22

9:29 am-3:49 pm

1 stop5h 20m

$431

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 12/11

6:10 am-11:55 am

1 stop6h 45m

Chicago Midway

Sun 12/14

6:00 am-12:00 pm

1 stop5h 00m

$431

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 12/11

12:55 pm-6:27 pm

1 stop6h 32m

Chicago O'Hare Intl

Sun 12/14

6:45 am-11:59 am

1 stop4h 14m

$431

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 12/23

6:56 pm-11:42 pm

1 stop5h 46m

Chicago O'Hare Intl

Wed 12/31

2:13 pm-5:26 pm

Nonstop2h 13m

$434

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 12/23

11:04 am-4:47 pm

1 stop6h 43m

Chicago O'Hare Intl

Thu 1/1

8:10 am-11:29 am

Nonstop2h 19m

$465

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Mon 11/17

12:10 pm-11:28 pm

1 stop12h 18m

Chicago O'Hare Intl

Thu 11/20

10:00 am-11:28 am

1 stop24h 28m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 38 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, January is the cheapest month in which you can book a flight from Westchester County to Chicago (average of $277). Flying from Westchester County to Chicago in October is currently the most expensive (average of $380). 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 October 30, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 56% on flights from Westchester County to Chicago by exploring options for tickets in the evening.

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 October 30, 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
7.9
Good
7,998 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

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
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

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
11,035 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

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 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 5h 46m. Delta provides one of the quickest options available for as low as $434. There are 736 mi between Westchester County and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Consider Sun Country Air (100%), Alaska Airlines (83%) or American Airlines (82%) 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 $426, our data indicates the cheapest price to be $103. The most popular route (White Plains Westchester County - Chicago O'Hare Intl), is priced around $184.

  • 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, January is the cheapest month in which you can book a flight from Westchester County to Chicago (average of $277). Flying from Westchester County to Chicago in October is currently the most expensive (average of $380). 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
Porter
Benton Harbor

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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 airline flying from Westchester County to Chicago

Discover the top airline 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$349Average$480FlexibilityNo cancel feeOn-time71%

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