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$96+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/2312:08 pm
HPN
-
ORD
1 stop12h 29m
Multiple Airlines
Mon 3/26:51 pm
ORD
-
HPN
2 stops40h 56m
Multiple Airlines
Deal found 1/27$231
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 3/212:08 pm
HPN
-
ORD
1 stop12h 29m
Multiple Airlines
Thu 3/58:42 pm
ORD
-
HPN
2 stops14h 48m
Multiple Airlines
Deal found 1/26$234
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:08 pm
HPN
-
ORD
1 stop12h 29m
Multiple Airlines
Tue 3/36:02 pm
ORD
-
HPN
2 stops17h 45m
Multiple Airlines
Deal found 1/28$239
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:08 pm
HPN
-
ORD
1 stop12h 29m
Multiple Airlines
Wed 3/412:44 pm
ORD
-
HPN
2 stops21h 44m
Multiple Airlines
Deal found 1/28$243
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1012:08 pm
HPN
-
ORD
1 stop6h 08m
Multiple Airlines
Tue 4/146:31 am
ORD
-
HPN
2 stops29h 16m
Multiple Airlines
Deal found 1/28$277
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/612:08 pm
HPN
-
ORD
1 stop7h 22m
Multiple Airlines
Tue 4/146:31 am
ORD
-
HPN
2 stops29h 16m
Multiple Airlines
Deal found 1/28$283
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1012:08 pm
HPN
-
ORD
1 stop6h 08m
Multiple Airlines
Mon 4/137:40 pm
ORD
-
HPN
2 stops40h 07m
Multiple Airlines
Deal found 1/28$301
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/612:08 pm
HPN
-
ORD
1 stop7h 22m
Multiple Airlines
Mon 4/137:40 pm
ORD
-
HPN
2 stops40h 07m
Multiple Airlines
Deal found 1/28$306
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/2712:08 pm
HPN
-
ORD
1 stop12h 29m
Multiple Airlines
Sun 3/16:51 pm
ORD
-
HPN
2 stops25h 08m
Multiple Airlines
Deal found 1/27$309
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2412:08 pm
HPN
-
ORD
2 stops12h 30m
Multiple Airlines
Sun 3/2912:34 pm
ORD
-
HPN
1 stop21h 54m
Multiple Airlines
Deal found 1/28$317
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/158:00 am
HPN
-
ORD
2 stops27h 52m
Multiple Airlines
Thu 3/1912:34 pm
ORD
-
HPN
1 stop21h 54m
Multiple Airlines
Deal found 1/28$331
This Delta deal was found by Cheapflights users on 1/27. 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 3/1412:35 pm
HPN
-
MDW
1 stop6h 19m
Delta
Sat 3/219:30 am
MDW
-
HPN
1 stop6h 05m
Delta
Deal found 1/27$375

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 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$231
(Kiwi.com)

One-way from

$96
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$187
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. 9% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 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 29, 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

Sat 2/14

5:29 pm-7:17 pm

Nonstop2h 48m

Chicago O'Hare Intl

Sat 2/14

9:37 pm-10:58 am

2 stops12h 21m

$348

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 4/8

12:35 pm-8:17 pm

1 stop8h 42m

Chicago O'Hare Intl

Wed 4/15

7:00 am-3:49 pm

1 stop7h 49m

$367

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 4/25

5:17 pm-10:28 pm

1 stop6h 11m

Chicago Midway

Tue 4/28

10:43 am-6:14 pm

1 stop6h 31m

$375

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 3/14

12:35 pm-5:54 pm

1 stop6h 19m

Chicago Midway

Sat 3/21

9:30 am-4:35 pm

1 stop6h 05m

$375

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 3/10

4:29 pm-11:54 pm

1 stop8h 25m

Chicago O'Hare Intl

Tue 3/31

11:10 am-6:18 pm

1 stop6h 08m

$375

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 3/3

3:15 pm-9:30 pm

1 stop7h 15m

Chicago O'Hare Intl

Sat 3/7

8:50 am-4:32 pm

1 stop6h 42m

$375

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 3/14

3:13 pm-7:49 pm

1 stop5h 36m

Chicago O'Hare Intl

Sat 3/21

5:30 am-12:03 pm

1 stop5h 33m

$375

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Mon 4/6

6:59 pm-8:30 am

1 stop14h 31m

Chicago O'Hare Intl

Tue 4/14

8:50 am-4:40 pm

1 stop6h 50m

$380

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 3/24

11:29 am-3:20 pm

1 stop4h 51m

Chicago O'Hare Intl

Sun 3/29

6:38 pm-9:59 pm

Nonstop2h 21m

$399

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 3/21

7:47 am-2:16 pm

1 stop7h 29m

Chicago O'Hare Intl

Sun 3/29

12:50 pm-3:59 pm

Nonstop2h 09m

$399

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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 $335). Flying from Westchester County to Chicago in February is currently the most expensive (average of $400). 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 29, 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.

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 January 29, 2026.

The most flights from zzREU to CHI are scheduled on a Thursday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 January 29, 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
8,128 reviews

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

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
7.9
Good
8,128 reviews
Delta
7.9
Good
8,128 reviews

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

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
11,205 reviews
Delta
7.9
Good
8,128 reviews

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

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 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 48m. American Airlines provides one of the quickest options available for as low as $348. 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 Qatar Airways (77%), American Airlines (73%) or Envoy Air (73%) 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 $385, our data indicates the cheapest price to be $148. The most popular route (White Plains Westchester County - Chicago O'Hare Intl), is priced around $239.

  • 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 $335). Flying from Westchester County to Chicago in February is currently the most expensive (average of $400). 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 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$364Average$480FlexibilityNo cancel feeOn-time71%

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