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$100+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Jan 31 — Feb 71
Sat 1/31
Sat 2/7
1 adult, Economy
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Cheap flight deals from Westchester County to Chicago

Best flights from Westchester County to Chicago
Discover carefully curated flight deals from Westchester County to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 1, 2026.

This American Airlines deal was found by Cheapflights users on 12/31. 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 4/214:30 pmHPN - ORD
Nonstop2h 49mAmerican Airlines
Sat 4/251:40 pmORD - HPN
Nonstop2h 20mAmerican Airlines
Deal found 12/31$349
This Delta deal was found by Cheapflights users on 1/1. 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 2/65:12 pmHPN - MDW
1 stop16h 40mDelta
Thu 2/191:26 pmMDW - HPN
1 stop25h 23mDelta
Deal found 1/1$367
This Delta deal was found by Cheapflights users on 1/1. 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 1/315:15 pmHPN - MDW
1 stop6h 07mDelta
Sat 2/76:25 amMDW - HPN
1 stop7h 00mDelta
Deal found 1/1$369
This American Airlines deal was found by Cheapflights users on 12/31. 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 5/296:56 pmHPN - ORD
1 stop6h 03mAmerican Airlines
Tue 6/27:38 pmORD - HPN
Nonstop2h 21mAmerican Airlines
Deal found 12/31$390
This Delta deal was found by Cheapflights users on 12/31. 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 6/912:45 pmHPN - MDW
1 stop6h 46mDelta
Wed 6/249:30 amMDW - HPN
1 stop6h 03mDelta
Deal found 12/31$369
This Delta deal was found by Cheapflights users on 12/31. 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 6/612:45 pmHPN - MDW
1 stop6h 46mDelta
Wed 6/249:30 amMDW - HPN
1 stop6h 03mDelta
Deal found 12/31$369
This Delta deal was found by Cheapflights users on 12/31. 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 6/1012:45 pmHPN - MDW
1 stop6h 46mDelta
Sat 6/279:30 amMDW - HPN
1 stop6h 03mDelta
Deal found 12/31$369
This Delta deal was found by Cheapflights users on 1/1. 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 5/1212:45 pmHPN - MDW
1 stop6h 46mDelta
Wed 5/209:30 amMDW - HPN
1 stop6h 03mDelta
Deal found 1/1$369
This Delta deal was found by Cheapflights users on 12/31. 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 6/912:45 pmHPN - MDW
1 stop6h 46mDelta
Sat 6/279:20 amMDW - HPN
1 stop6h 20mDelta
Deal found 12/31$369
This Delta deal was found by Cheapflights users on 12/31. 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 6/64:19 pmHPN - MDW
1 stop6h 26mDelta
Tue 6/239:20 amMDW - HPN
1 stop6h 20mDelta
Deal found 12/31$369
This Delta deal was found by Cheapflights users on 12/31. 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 6/103:15 pmHPN - ORD
1 stop5h 28mDelta
Tue 6/2310:35 amORD - HPN
1 stop4h 58mDelta
Deal found 12/31$369
This Delta deal was found by Cheapflights users on 1/1. 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 5/126:40 pmHPN - ORD
1 stop6h 15mDelta
Wed 5/206:00 amORD - HPN
1 stop5h 14mDelta
Deal found 1/1$369
This Delta deal was found by Cheapflights users on 1/1. 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 2/205:12 pmHPN - ORD
1 stop17h 29mDelta
Sun 2/226:30 amORD - HPN
1 stop4h 26mDelta
Deal found 1/1$399
This Delta deal was found by Cheapflights users on 12/31. 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 6/912:45 pmHPN - MDW
1 stop6h 46mDelta
Mon 6/296:00 amMDW - HPN
1 stop5h 14mDelta
Deal found 12/31$400
This Delta deal was found by Cheapflights users on 1/1. 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 2/75:15 pmHPN - MDW
1 stop6h 07mDelta
Sat 2/216:00 amMDW - HPN
1 stop7h 28mDelta
Deal found 1/1$400
This Delta deal was found by Cheapflights users on 12/31. 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 6/1012:45 pmHPN - MDW
1 stop6h 46mDelta
Mon 6/296:00 amMDW - HPN
1 stop5h 14mDelta
Deal found 12/31$400
This Delta deal was found by Cheapflights users on 1/1. 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 2/75:15 pmHPN - MDW
1 stop6h 07mDelta
Fri 2/206:00 amMDW - HPN
1 stop7h 28mDelta
Deal found 1/1$400
This Delta deal was found by Cheapflights users on 12/31. 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 6/612:45 pmHPN - ORD
1 stop4h 51mDelta
Mon 6/291:15 pmORD - HPN
1 stop7h 26mDelta
Deal found 12/31$400
This Delta deal was found by Cheapflights users on 12/31. 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 6/66:40 pmHPN - ORD
1 stop6h 15mDelta
Sun 6/76:00 amORD - HPN
1 stop5h 14mDelta
Deal found 12/31$400
This Delta deal was found by Cheapflights users on 1/1. 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 3/3112:35 pmHPN - ORD
1 stop5h 08mDelta
Sun 4/58:55 amORD - HPN
1 stop6h 42mDelta
Deal found 1/1$400
This Delta deal was found by Cheapflights users on 1/1. 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 3/125:17 pmHPN - ORD
1 stop3h 57mDelta
Sat 3/147:10 amORD - HPN
1 stop3h 33mDelta
Deal found 1/1$400
This Delta deal was found by Cheapflights users on 12/31. 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 6/93:15 pmHPN - ORD
1 stop5h 28mDelta
Sun 6/288:55 amORD - HPN
1 stop6h 38mDelta
Deal found 12/31$400
This Delta deal was found by Cheapflights users on 1/1. 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 2/256:43 pmHPN - ORD
1 stop6h 13mDelta
Sun 3/110:35 amORD - HPN
1 stop4h 14mDelta
Deal found 1/1$400
This Delta deal was found by Cheapflights users on 12/31. 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 6/126:40 pmHPN - ORD
1 stop6h 15mDelta
Wed 6/2410:35 amORD - HPN
1 stop4h 58mDelta
Deal found 12/31$400

Find 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 January 1, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$322
(Kiwi.com)

One-way from

$100
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$179
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
Search Deals
From Westchester County to Chicago (CHI)
Search Deals
One-way flight from Westchester County to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($21 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 January 2026
Search Deals

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 January 1, 2026.
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 - ORD

HPNORD

White Plains Westchester County

Tue 4/21

4:30 pm-6:19 pm

Nonstop2h 49m

Chicago O'Hare Intl

Sat 4/25

1:40 pm-5:00 pm

Nonstop2h 20m

$349

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 2/6

5:12 pm-8:52 am

1 stop16h 40m

Chicago Midway

Thu 2/19

1:26 pm-3:49 pm

1 stop25h 23m

$367

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 1/31

5:15 pm-10:22 pm

1 stop6h 07m

Chicago Midway

Sat 2/7

6:25 am-2:25 pm

1 stop7h 00m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 6/9

12:45 pm-6:31 pm

1 stop6h 46m

Chicago Midway

Wed 6/24

9:30 am-4:33 pm

1 stop6h 03m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 6/6

12:45 pm-6:31 pm

1 stop6h 46m

Chicago Midway

Wed 6/24

9:30 am-4:33 pm

1 stop6h 03m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 6/10

12:45 pm-6:31 pm

1 stop6h 46m

Chicago Midway

Sat 6/27

9:30 am-4:33 pm

1 stop6h 03m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 5/12

12:45 pm-6:31 pm

1 stop6h 46m

Chicago Midway

Wed 5/20

9:30 am-4:33 pm

1 stop6h 03m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 6/9

12:45 pm-6:31 pm

1 stop6h 46m

Chicago Midway

Sat 6/27

9:20 am-4:40 pm

1 stop6h 20m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 6/6

4:19 pm-9:45 pm

1 stop6h 26m

Chicago Midway

Tue 6/23

9:20 am-4:40 pm

1 stop6h 20m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 6/10

3:15 pm-7:43 pm

1 stop5h 28m

Chicago O'Hare Intl

Tue 6/23

10:35 am-4:33 pm

1 stop4h 58m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/1

Showing 1-10 of 41 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, February is the cheapest month in which you can book a flight from Westchester County to Chicago (average of $300). 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 January 1, 2026.

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.

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 January 1, 2026.
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
8,021 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

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
8,021 reviews
Delta
7.9
Good
8,021 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

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
11,075 reviews
Delta
7.9
Good
8,021 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

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 2h 49m. American Airlines provides one of the quickest options available for as low as $349. 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 American Airlines (69%), Envoy Air (69%) or Qatar Airways (67%) 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 $783, our data indicates the cheapest price to be $169. The most popular route (White Plains Westchester County - Chicago O'Hare Intl), is priced around $322.

  • 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, February is the cheapest month in which you can book a flight from Westchester County to Chicago (average of $300). 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
Lansing
Merrillville
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 January 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$359Average$479FlexibilityNo cancel feeOn-time71%

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