Cheap flights from Chicago (CHI) to Westchester County from $191
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 5/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — HPN
May 1 — May 81
From?
To?
1 adult, Economy
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How far in advance should I book a flight from Chicago to Westchester County?
To save on the cost of your flight from Chicago to Westchester County, book at least 54 days before your planned departure. Booking around this time can save you about 109% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $266 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $381.
What is the cheapest month to fly from Chicago to Westchester County?
Our data shows that January tends to be the cheapest month to fly to Westchester County from Chicago. Users have commonly found prices around $235 for the month, but tickets can be as low as $108. Due to multiple factors, prepare for potentially higher prices in June.
When is the cheapest time to fly from Chicago to Westchester County (CHI - REU)?
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Westchester County as you normally would.
Cheap American Airlines flights from Chicago to Westchester County
Explore cheap flight options specifically provided by American Airlines for the route between Chicago and Westchester County. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,068,117 searches. Data last updated April 26, 2024.
Consider these cheap American Airlines flights we've found departing from Chicago to Westchester County. Deals update often to give you more flight options matching your criteria
Tue 6/256:31 amORD - HPN
1 stop10h 45mAmerican Airlines
Wed 6/264:30 pmHPN - ORD
Nonstop2h 33mAmerican Airlines
Deal found 4/25$426
Sat 6/299:45 amORD - HPN
1 stop6h 10mAmerican Airlines
Tue 7/95:25 pmHPN - ORD
1 stop14h 45mAmerican Airlines
Deal found 4/25$434
Tue 5/2112:51 pmORD - HPN
Nonstop2h 08mAmerican Airlines
Sat 5/254:30 pmHPN - ORD
Nonstop2h 31mAmerican Airlines
Deal found 4/26$435
Fri 8/98:15 amORD - HPN
Nonstop2h 17mAmerican Airlines
Tue 8/1311:30 amHPN - ORD
1 stop9h 10mAmerican Airlines
Deal found 4/25$436
Wed 6/56:15 amORD - HPN
1 stop5h 56mAmerican Airlines
Wed 6/54:30 pmHPN - ORD
Nonstop2h 33mAmerican Airlines
Deal found 4/25$437
Tue 5/2112:51 pmORD - HPN
Nonstop2h 08mAmerican Airlines
Sat 5/257:30 amHPN - ORD
1 stop5h 38mAmerican Airlines
Deal found 4/25$443
Fri 8/94:50 pmORD - HPN
1 stop4h 36mAmerican Airlines
Tue 8/1311:30 amHPN - ORD
1 stop9h 10mAmerican Airlines
Deal found 4/25$444
Wed 6/58:30 amORD - HPN
1 stop7h 25mAmerican Airlines
Wed 6/56:46 pmHPN - ORD
1 stop6h 12mAmerican Airlines
Deal found 4/25$445
Sat 5/186:42 pmORD - HPN
Nonstop2h 17mAmerican Airlines
Mon 5/204:30 pmHPN - ORD
Nonstop2h 31mAmerican Airlines
Deal found 4/25$446
Cheap Delta flights from Chicago to Westchester County
Explore cheap flight options specifically provided by Delta for the route between Chicago and Westchester County. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,068,117 searches. Data last updated April 26, 2024.
Browse through some of the cheapest Delta flights traveling from Chicago to Westchester County. Make sure to examine the flight information before completing your reservation.
Tue 8/2710:35 amORD - HPN
1 stop24h 09mDelta
Sat 8/3112:30 pmHPN - ORD
1 stop9h 41mDelta
Deal found 4/25$293
Thu 5/308:45 amORD - HPN
1 stop7h 04mDelta
Mon 6/35:29 pmHPN - ORD
1 stop15h 11mDelta
Deal found 4/25$366
Sat 5/257:09 amORD - HPN
1 stop8h 40mDelta
Wed 5/295:29 pmHPN - ORD
1 stop15h 11mDelta
Deal found 4/25$369
Sat 5/257:09 amORD - HPN
1 stop8h 40mDelta
Tue 5/285:29 pmHPN - ORD
1 stop15h 11mDelta
Deal found 4/25$372
Tue 8/273:50 pmORD - HPN
2 stops18h 54mDelta
Sat 8/3112:30 pmHPN - ORD
1 stop9h 41mDelta
Deal found 4/25$375
Tue 5/218:45 amORD - HPN
1 stop7h 04mDelta
Wed 5/295:29 pmHPN - ORD
1 stop15h 11mDelta
Deal found 4/25$379
Tue 5/218:45 amORD - HPN
1 stop7h 04mDelta
Tue 5/285:29 pmHPN - ORD
1 stop15h 11mDelta
Deal found 4/25$382
Mon 5/207:12 pmORD - HPN
1 stop15h 40mDelta
Wed 5/2912:45 pmHPN - ORD
1 stop19h 55mDelta
Deal found 4/25$409
Mon 5/207:12 pmORD - HPN
1 stop15h 40mDelta
Tue 5/285:29 pmHPN - ORD
1 stop15h 11mDelta
Deal found 4/25$412
Cheap Chicago to Westchester County flights in April & May 2024
Find cheap flight options from Chicago to Westchester County specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,068,117 searches. Prices were last updated on April 26, 2024.
Scroll through some of the best deals on flights from Chicago to Westchester County in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Thu 5/307:07 pmORD - HPN
2 stops16h 23mMultiple Airlines
Mon 6/31:10 pmHPN - ORD
2 stops21h 45mMultiple Airlines
Deal found 4/25$253
Thu 5/307:07 pmORD - HPN
2 stops16h 23mMultiple Airlines
Mon 6/31:10 pmHPN - ORD
3 stops27h 48mMultiple Airlines
Deal found 4/25$276
Sun 5/59:25 pmORD - HPN
2 stops14h 05mMultiple Airlines
Fri 5/107:49 pmHPN - ORD
3 stops21h 46mMultiple Airlines
Deal found 4/25$334
Fri 5/318:30 pmORD - HPN
3 stops21h 38mMultiple Airlines
Mon 6/31:10 pmHPN - ORD
2 stops21h 45mMultiple Airlines
Deal found 4/24$337
Thu 5/3012:28 pmORD - HPN
3 stops23h 02mMultiple Airlines
Mon 6/37:49 pmHPN - ORD
3 stops24h 56mMultiple Airlines
Deal found 4/25$346
Fri 5/318:30 pmORD - HPN
3 stops21h 38mMultiple Airlines
Mon 6/37:49 pmHPN - ORD
3 stops25h 35mMultiple Airlines
Deal found 4/24$351
Thu 5/95:36 pmORD - HPN
2 stops24h 32mMultiple Airlines
Mon 5/137:49 pmHPN - ORD
3 stops25h 35mMultiple Airlines
Deal found 4/24$365
Thu 5/308:45 amORD - HPN
1 stop7h 04mDelta
Mon 6/35:29 pmHPN - ORD
1 stop15h 11mDelta
Deal found 4/25$366
Thu 5/95:36 pmORD - HPN
2 stops24h 32mMultiple Airlines
Mon 5/131:10 pmHPN - ORD
2 stops21h 45mMultiple Airlines
Deal found 4/24$368
Chicago to Westchester County 2024 flight deals
Discover exclusive flight deals for travel between Chicago and Westchester County in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,068,117 searches. Data last updated April 26, 2024.
Scroll through some of the best deals on flights from Chicago to Westchester County in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Thu 5/307:07 pmORD - HPN
2 stops16h 23mMultiple Airlines
Mon 6/31:10 pmHPN - ORD
2 stops21h 45mMultiple Airlines
Deal found 4/25$253
Thu 5/307:07 pmORD - HPN
2 stops16h 23mMultiple Airlines
Mon 6/31:10 pmHPN - ORD
3 stops27h 48mMultiple Airlines
Deal found 4/25$276
Tue 8/2710:35 amORD - HPN
1 stop24h 09mDelta
Sat 8/3112:30 pmHPN - ORD
1 stop9h 41mDelta
Deal found 4/25$293
Thu 6/68:04 pmORD - HPN
2 stops22h 04mMultiple Airlines
Tue 6/117:40 pmHPN - ORD
3 stops23h 00mMultiple Airlines
Deal found 4/25$333
Sun 5/59:25 pmORD - HPN
2 stops14h 05mMultiple Airlines
Fri 5/107:49 pmHPN - ORD
3 stops21h 46mMultiple Airlines
Deal found 4/25$334
Fri 5/318:30 pmORD - HPN
3 stops21h 38mMultiple Airlines
Mon 6/31:10 pmHPN - ORD
2 stops21h 45mMultiple Airlines
Deal found 4/24$337
Sat 11/210:11 amMDW - HPN
1 stop11h 05mDelta
Tue 11/56:55 pmHPN - MDW
1 stop24h 04mDelta
Deal found 4/25$344
Thu 5/3012:28 pmORD - HPN
3 stops23h 02mMultiple Airlines
Mon 6/37:49 pmHPN - ORD
3 stops24h 56mMultiple Airlines
Deal found 4/25$346
Sat 11/210:11 amMDW - HPN
1 stop11h 05mDelta
Tue 11/55:20 pmHPN - MDW
2 stops22h 36mDelta
Deal found 4/24$349
Non-stop flights to Westchester County from Chicago
Discover non-stop flight options from Chicago to Westchester County. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 3,068,117 searches. Data last updated April 26, 2024.
Consider booking one of these non-stop flights heading from Chicago to Westchester County. Users seeking other options on flights from Chicago to Westchester County should update the search form at the top of the page.
Sat 6/296:37 pmORD - HPN
Nonstop2h 22mAmerican Airlines
Tue 7/912:00 pmHPN - ORD
Nonstop2h 31mAmerican Airlines
Deal found 4/25$435
Sat 5/186:42 pmORD - HPN
Nonstop2h 17mAmerican Airlines
Sun 5/264:30 pmHPN - ORD
Nonstop2h 31mAmerican Airlines
Deal found 4/25$445
Sat 5/186:42 pmORD - HPN
Nonstop2h 17mAmerican Airlines
Mon 5/204:30 pmHPN - ORD
Nonstop2h 31mAmerican Airlines
Deal found 4/25$446
Thu 6/138:09 amORD - HPN
Nonstop2h 18mAmerican Airlines
Sun 6/167:20 amHPN - ORD
Nonstop2h 33mAmerican Airlines
Deal found 4/25$455
Tue 5/288:15 amORD - HPN
Nonstop2h 11mAmerican Airlines
Wed 5/294:30 pmHPN - ORD
Nonstop2h 31mAmerican Airlines
Deal found 4/25$469
Sat 5/186:42 pmORD - HPN
Nonstop2h 17mAmerican Airlines
Sun 5/197:04 amHPN - ORD
Nonstop2h 31mAmerican Airlines
Deal found 4/25$519
Thu 5/1612:51 pmORD - HPN
Nonstop2h 08mAmerican Airlines
Sun 5/1912:29 pmHPN - ORD
Nonstop2h 31mAmerican Airlines
Deal found 4/25$529
Thu 5/308:15 amORD - HPN
Nonstop2h 11mAmerican Airlines
Mon 6/34:30 pmHPN - ORD
Nonstop2h 31mAmerican Airlines
Deal found 4/25$531
Thu 5/912:51 pmORD - HPN
Nonstop2h 08mAmerican Airlines
Thu 5/1612:29 pmHPN - ORD
Nonstop2h 31mAmerican Airlines
Deal found 4/25$533
Chicago to Westchester County flights leaving soon
Find last-minute flight options from Chicago to Westchester County for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,068,117 searches. Data last updated April 26, 2024.
Consider one of these great deals we found on last-minute flights from Chicago to Westchester County. Tip: verify your flight details before completing your reservation.
Sun 5/59:25 pmORD - HPN
2 stops14h 05mMultiple Airlines
Fri 5/107:49 pmHPN - ORD
3 stops21h 46mMultiple Airlines
Deal found 4/25$334
Thu 5/29:25 pmORD - HPN
2 stops14h 05mMultiple Airlines
Mon 5/67:49 pmHPN - ORD
3 stops39h 06mMultiple Airlines
Deal found 4/25$391
Thu 5/27:03 amORD - HPN
3 stops28h 27mMultiple Airlines
Mon 5/67:49 pmHPN - ORD
3 stops39h 06mMultiple Airlines
Deal found 4/25$447
Sun 5/59:25 pmORD - HPN
2 stops14h 05mMultiple Airlines
Fri 5/101:10 pmHPN - ORD
2 stops11h 19mMultiple Airlines
Deal found 4/25$453
Sun 5/511:20 amORD - HPN
3 stops24h 10mMultiple Airlines
Fri 5/107:49 pmHPN - ORD
3 stops28h 40mMultiple Airlines
Deal found 4/25$472
Thu 5/29:25 pmORD - HPN
2 stops14h 05mMultiple Airlines
Thu 5/97:49 pmHPN - ORD
3 stops28h 40mMultiple Airlines
Deal found 4/25$510
Thu 5/29:25 pmORD - HPN
2 stops14h 05mMultiple Airlines
Thu 5/97:49 pmHPN - ORD
2 stops20h 22mMultiple Airlines
Deal found 4/25$519
Sun 5/55:34 amORD - HPN
1 stop5h 26mDelta
Sat 5/1112:45 pmHPN - ORD
1 stop4h 46mDelta
Deal found 4/25$535
Thu 5/25:34 amORD - HPN
1 stop5h 26mDelta
Sun 5/55:50 amHPN - ORD
1 stop4h 35mDelta
Deal found 4/25$551
One-way flights to Westchester County from Chicago
Search for one-way flight options from Chicago to Westchester County. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,068,117 searches. Data last updated April 26, 2024.
If you're seeking multiple options on one-way flights from Chicago to Westchester County, be sure to check out these deals, which are updated often. Those seeking round-trip flights from Chicago to Westchester County should utilize the search form at the the top of the page.
Sun 5/59:25 pmORD - HPN
2 stops14h 05mMultiple Airlines
Deal found 4/25$191
Thu 5/29:25 pmORD - HPN
2 stops14h 05mMultiple Airlines
Deal found 4/25$203
Sun 6/168:04 pmORD - HPN
2 stops22h 04mMultiple Airlines
Deal found 4/25$204
Tue 8/138:20 amORD - HPN
1 stop9h 05mAmerican Airlines
Deal found 4/25$215
Tue 5/288:45 amORD - HPN
1 stop7h 04mDelta
Deal found 4/25$217
Wed 6/121:30 pmORD - HPN
1 stop8h 53mAmerican Airlines
Deal found 4/25$240
Thu 5/166:40 pmORD - HPN
3 stops23h 28mMultiple Airlines
Deal found 4/25$246
Fri 6/215:05 amORD - HPN
2 stops14h 54mMultiple Airlines
Deal found 4/25$254
Fri 8/98:20 amORD - HPN
1 stop9h 05mAmerican Airlines
Deal found 4/25$255
Find flights from Chicago to Westchester County within your budget
Customize your flight search to find flights from Chicago to Westchester County 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 3,068,117 searches. Data last updated April 26, 2024.
Fly from
Any airport
Fly to
Any airport
Budget
$253 - $434
Route
Depart
Return
Price
Chicago O'Hare IntlWhite Plains Westchester County
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Thu 5/30
2 stops16h 23m
White Plains Westchester County
Mon 6/3
2 stops21h 45m
$253
Chicago O'Hare IntlWhite Plains Westchester County
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Thu 5/30
2 stops16h 23m
White Plains Westchester County
Mon 6/3
3 stops27h 48m
$276
Chicago O'Hare IntlWhite Plains Westchester County
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Tue 8/27
1 stop24h 09m
White Plains Westchester County
Sat 8/31
1 stop9h 41m
$293
Chicago O'Hare IntlWhite Plains Westchester County
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Thu 6/6
2 stops22h 04m
White Plains Westchester County
Tue 6/11
3 stops23h 00m
$333
Chicago O'Hare IntlWhite Plains Westchester County
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Fri 5/31
3 stops21h 38m
White Plains Westchester County
Mon 6/3
2 stops21h 45m
$337
Chicago O'Hare IntlWhite Plains Westchester County
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Thu 5/30
1 stop7h 04m
White Plains Westchester County
Mon 6/3
1 stop15h 11m
$366
Chicago O'Hare IntlWhite Plains Westchester County
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Sat 5/25
1 stop8h 40m
White Plains Westchester County
Wed 5/29
1 stop15h 11m
$369
Chicago O'Hare IntlWhite Plains Westchester County
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Tue 6/25
1 stop10h 45m
White Plains Westchester County
Wed 6/26
Nonstop2h 33m
$426
Chicago O'Hare IntlWhite Plains Westchester County
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Sat 6/29
1 stop6h 10m
White Plains Westchester County
Tue 7/9
1 stop14h 45m
$434
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Westchester County
Get insights into the airlines that provide service to Westchester County. 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 Westchester County. Reviews last updated April 26, 2024.
Read through reviews of airlines operating flights from Chicago to Westchester County, such as American Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
10,966 reviews
Entertainment
8.0
Food
7.4
Overall
8.1
Boarding
8.2
Crew
8.6
Comfort
7.9
Reviews
1 / 10
On time flights; courteous staff; efficient boarding system! Thank you!
10,966 reviews
10,966 reviews
Entertainment
8.0
Food
7.4
Overall
8.1
Boarding
8.2
Crew
8.6
Comfort
7.9
Reviews
1 / 10
On time flights; courteous staff; efficient boarding system! Thank you!
14,889 reviews
10,966 reviews
Entertainment
8.0
Food
7.4
Overall
8.1
Boarding
8.2
Crew
8.6
Comfort
7.9
Reviews
1 / 10
On time flights; courteous staff; efficient boarding system! Thank you!
Related info for your journey
Find useful and relevant information for your journey from Chicago to Westchester County. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Westchester CountySee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
Top 3 airlines flying from Chicago to Westchester County
Discover the top 3 airlines that operate flights from Chicago to Westchester County. 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 3,068,117 searches. Data last updated April 26, 2024.
Search flights from Chicago to Westchester County by cabin class
Find flights from Chicago to Westchester County, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hourly flight availability from Chicago to Westchester County
Find hourly flight availability from Chicago to Westchester County. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 26, 2024.
| 1%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 46%of flight departures | Morning6 am to noon |
| 53%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
Midnight
6 AM
Noon
6 PM
Book a flight to one of these trending destinations
User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Fly with Cheapflights
Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from Chicago to Westchester County?
Cheapflights makes it easy to find Chicago to Westchester County flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
Why should you use Cheapflights to find cheap flight tickets from Chicago to Westchester County?
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Westchester County from Chicago.
Can Cheapflights find flights from Chicago to Westchester County with no change fees?
Need flexible booking options for your flight to Westchester County from Chicago? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.
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Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!