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Chicago to Westchester Flights

Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from Chicago to Westchester

Departure Arrival Travel dates Round-trip
CHI HPN Fri, Apr 24 - Sun, Apr 26 $324
CHI HPN Fri, Apr 24 - Sun, Apr 26 $324
CHI HPN Fri, Jan 30 - Sun, Feb 1 $386
CHI HPN Thu, Jan 22 - Sun, Jan 25 $403

Chicago and Westchester airports and terminals

Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from ORD to HPN

    Terminal Carriers
    Terminal 1 United Airlines
    Terminal 2 United Airlines
    Terminal 3 American Airlines, British Airways, Qatar Airways, US Airways
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Airports in Westchester NY, US
map of airports in Westchester
  • 1

    JFK Airport (JFK)

    Distance from City Center: 29.7 miles

  • 2

    LaGuardia Airport (LGA)

    Distance from City Center: 22 miles

  • 3

    Newark Airport (EWR)

    Distance from City Center: 35.7 miles

  • 4

    Stewart (SWF)

    Distance from City Center: 36.7 miles

  • 5

    Danbury Airport (DXR)

    Distance from City Center: 25 miles

  • 6

    New Haven Airport (HVN)

    Distance from City Center: 44.6 miles

  • 7

    Westchester County Airport (HPN)

    Distance from City Center: 0.1 miles

    Carriers for flights from CHI to HPN

    Carriers
    American Airlines, British Airways, Qatar Airways, US Airways, United Airlines
  • 8

    Municipal (MMU)

    Distance from City Center: 42 miles

  • 9

    Long Island Macarthur (ISP)

    Distance from City Center: 36.7 miles

Back to menu Return to top
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$324
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Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Westchester Airport Hotels

Hotel only $126

Doral Arrowwood

4 stars
3.8 / 5 8 reviews

975 Anderson Hill Rd Map

Save up to $28 USD on your stay

The Doral Arrowwood consists of 373 guest rooms and is located on 114 wooded acres in a quiet corner of Westchester County.... More

Hotel only $94

La Quinta Inn & Suites Armonk Westchester County Airport

3 stars
3.2 / 5 91 reviews

94 Business Park Dr Map

Nestled in peaceful Westchester County, our full-service La Quinta Inn & Suites Armonk Westchester County Airport is HERE FOR YOU!... More

Hotel only $129

HYATT house White Plains

3 stars
4.5 / 5 42 reviews

101 Corporate Park Dr Map

The HYATT house White Plains is a159-room all suite hotel located in suburban Westchester. Our 1-bed and 2-bed/2-bath suites feature fully-equipped, full-size kitchens, ice-maker, sleeper sofa,... More

Hotel only $110

Renaissance Westchester Hotel

4 stars
4.0 / 5 61 reviews

80 Map

Rate includes breakfast

Delight in the resort atmosphere of Renaissance Westchester Hotel in White Plains, NY, nestled on 30 acres of scenic countryside in Westchester County.... More

Hotel only $119

Crowne Plaza WHITE PLAINS-DOWNTOWN

4 stars
4.0 / 5 61 reviews

66 Hale Avenue Map

...The Top Choice of Hotels in White Plains, NY Crowne Plaza® is located in downtown White Plains, the heart of Westchester County.... If youre looking for hotels near Westchester Airport, we are... More

Hotel only $109

Cambria Suites White Plains - Downtown

3 stars
4.0 / 5 1 reviews

250 Main Street Map

...Free transportation within a five-mile radius is provided, including to Westchester County Airport.... More

January

Cheapest weekend flights in January from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Jan 17 Chicago (ORD) Westchester (HPN) US Airways $324
Earn $3.24
Return Mon, Jan 19 Westchester (HPN) Chicago (ORD) US Airways

Lowest roundtrip airfare in January from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Jan 17 Chicago (ORD) Westchester (HPN) US Airways $324
Earn $3.24
Return Mon, Jan 19 Westchester (HPN) Chicago (ORD) US Airways

Best one-week trip in January from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Jan 25 Chicago (ORD) Westchester (HPN) US Airways $324
Earn $3.24
Return Sun, Feb 1 Westchester (HPN) Chicago (ORD) US Airways
Back to menu Return to top

February

Cheapest weekend flights in February from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Feb 6 Chicago (ORD) Westchester (HPN) US Airways $324
Earn $3.24
Return Mon, Feb 9 Westchester (HPN) Chicago (ORD) US Airways

Lowest roundtrip airfare in February from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Feb 6 Chicago (ORD) Westchester (HPN) US Airways $324
Earn $3.24
Return Mon, Feb 9 Westchester (HPN) Chicago (ORD) US Airways
Back to menu Return to top

March

Cheapest weekend flights in March from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Mar 19 Chicago (ORD) Westchester (HPN) US Airways $364
Earn $3.64
Return Mon, Mar 23 Westchester (HPN) Chicago (ORD) US Airways

Lowest roundtrip airfare in March from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Mar 19 Chicago (ORD) Westchester (HPN) US Airways $364
Earn $3.64
Return Mon, Mar 23 Westchester (HPN) Chicago (ORD) US Airways

Best one-week trip in March from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Mar 15 Chicago (ORD) Westchester (HPN) US Airways $384
Earn $3.84
Return Sun, Mar 22 Westchester (HPN) Chicago (ORD) US Airways
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Flights to Westchester

Airports in Chicago

The city of Chicago is primarily served by two international airports. Travelers looking for low-fare flights from Chicago can use Orbitz.com to find flights from both O'Hare and Midway. O'Hare International Airport is located approximately 17 miles northwest of downtown Chicago. Midway International Airport is located on the city's southwest side, approximately eight miles from Chicago's Loop. O'Hare serves as a hub for American Airlines and United Airlines, and Midway is a hub for Southwest Airlines.

Chicago Airport Parking

Daily, hourly, and valet parking are available at O'Hare. Rates vary from $2.00 to $10.00 per hour. An economy parking lot is also available at a rate of $2.00 per hour. Similar parking options and rates apply at Midway.

Chicago Airport Transportation

There are numerous transportation options for getting to and from both O'Hare and Midway. O'Hare can be accessed via regional trains, buses, and local mass transit lines. The CTA Blue Line offers a fast and convenient transportation option to and from this airport. Midway is served by the CTA Orange Line. Car rental services are available at both airports, and travelers can quickly book car rental services at either airport using Orbitz.com.

Chicago Airport Restaurants

Both O'Hare and Midway offer a variety of restaurant options for travelers. Restaurants located in both airports include Starbuck's Coffee, Chicago Style Hot Dogs, McDonald's, Auntie Anne's, Chili's, Cinnabon, and Dunkin Donuts, making it easy for visitors to grab a quick breakfast, snack, or meal. By using Orbitz.com, travelers can quickly and easily find low-fare flights from Chicago.

Airports in Westchester, NY

When you search for domestic flights to Westchester, NY, on Orbitz.com, you're certain to find the best possible deal. Westchester County is serviced by the Westchester County Airport, a small facility located about four miles outside White Plains. Twelve commercial airlines maintain regular flights to and from the airport, including Delta, jetBlue, American Airlines and United.

Transportation From the Airport

There are several ways to get from the airport into the surrounding county. Taxis and limousines offer quick access to nearby hotels. Because of the airport's central location within the county, you're never more than a few minutes away from lodging or attractions. The Bee-Line bus system also provides fast transport to local destinations, as well as connections to the MTA Metro-North Railroad and a direct path into New York City.

Weather in Westchester

The weather in Westchester varies depending on how near you are to the coast. Winters are cold and snowy, with lows dipping well below freezing. Summertime is hot, especially inland, where temperatures can soar into the 90s. Closer to the coast, refreshing ocean breezes keep the temperature more moderate.

Things to Do in Westchester

The Caramoor Center for Music and the Arts hosts an amazing 7-week outdoor festival each summer. Classical music and jazz fill the lush gardens with beautiful music. The nearby Katonah Museum of Art offers compelling exhibitions throughout the year. Also at the museum, the Children's Learning Center offers free admission to families and is fun for all ages. Make sure you look for discounts when you search for flights to Westchester through Orbitz.com.

Interesting facts about flights from Chicago to Westchester

    • 4 direct flights are operating from Chicago to Westchester today.
    • Today's average time for a direct flight is 2h 8m.
    • United Airlines flight 4512 (7:34 AM GMT, Embraer RJ135/RJ140/RJ145) is today's earliest available flight from Chicago to Westchester.
    • American Airlines flight 2796 (12:50 PM GMT, Embraer RJ140) is today's latest available flight from Chicago to Westchester.
    • Today's shortest direct flight from Chicago to Westchester (United Airlines flight 4512, Embraer RJ135/RJ140/RJ145) takes 2h 6m.
    • Today's longest direct flight from Chicago to Westchester (American Airlines flight 2796, Embraer RJ140) takes 2h 10m.
    • Flights from Midway Airport (MDW), O'Hare Airport (ORD) to Danbury Airport (DXR), JFK Airport (JFK), LaGuardia Airport (LGA), Long Island Macarthur (ISP), Municipal (MMU), New Haven Airport (HVN), Newark Airport (EWR), Stewart (SWF), Westchester County Airport (HPN) are available for this route.

Flight schedule for flights from Chicago to Westchester on Mon, Dec 29, 2014

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
American Airlines/American Airlines AA1910/AA4048 ORD 5:50 AM HPN 11:30 AM 321/CRJ 4hr 40min
American Airlines/US Airways AA1910/US4048 ORD 5:50 AM HPN 11:30 AM 321/CRJ 4hr 40min
US Airways/American Airlines US1910/AA4048 ORD 5:50 AM HPN 11:30 AM 321/CRJ 4hr 40min
US Airways/US Airways US1910/US4048 ORD 5:50 AM HPN 11:30 AM 321/CRJ 4hr 40min
American Airlines AA2763 ORD 9:10 AM HPN 12:23 PM ERD 2hr 13min
US Airways US8557 ORD 9:10 AM HPN 12:23 PM ERD 2hr 13min
American Airlines/American Airlines AA578/AA4851 ORD 7:30 AM HPN 1:11 PM 757/DH3 4hr 41min
American Airlines/US Airways AA578/US6167 ORD 7:30 AM HPN 1:11 PM 757/DH8 4hr 41min
American Airlines/American Airlines AA4324/AA4851 ORD 8:30 AM HPN 1:11 PM E75/DH3 3hr 41min
American Airlines/US Airways AA4324/US6167 ORD 8:30 AM HPN 1:11 PM E75/DH8 3hr 41min
US Airways/American Airlines US4340/AA4851 ORD 6:55 AM HPN 1:11 PM E75/DH3 5hr 16min
US Airways/US Airways US4340/US6167 ORD 6:55 AM HPN 1:11 PM E75/DH8 5hr 16min
US Airways/American Airlines US578/AA4851 ORD 7:30 AM HPN 1:11 PM 752/DH3 4hr 41min