Flights from Chicago to Westchester

Selected fares from Chicago to Westchester

Departure Arrival Travel dates Round-trip
CHI HPN Sat, Oct 3 - Mon, Oct 12 $324
CHI HPN Sat, Oct 3 - Mon, Oct 12 $324
CHI HPN Fri, May 29 - Mon, Jun 1 $409
CHI HPN Wed, May 27 - Tue, Jun 2 $417

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 2 United Airlines
    Terminal 3 American Airlines, US Airways
Back to menu Return to top

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, 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

  

Earn up to 5% on hotels and 1% on flights - It's free!

By clicking, I agree to the terms and conditions.

Sun Mon Tue Wed Thu Fri Sat
1 2
3 4 5 6 7 8 9
10 11 12 13 14 15
$324
16
$324
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Westchester Airport Hotels

Hotel only $120

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 $89

La Quinta Inn & Suites Armonk Westchester County Airport

3 stars
3.2 / 5 95 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 $134

HYATT house White Plains

3 stars
4.5 / 5 46 reviews

101 Corporate Park Dr Map

Save 30% on your stay

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 $131

Renaissance Westchester Hotel

4 stars
4.0 / 5 69 reviews

80 Map

Rate includes breakfast

Historic grandeur and modern convenience await you at the stunningly sophisticated Renaissance Westchester Hotel. Ideally located in the Hudson Valley, near Rye and Sleepy Hollow, our hotel... More

Hotel only $134

Hilton Westchester

3 stars
3.8 / 5 36 reviews

699 Westchester Avenue Map

Rate includes wireless internet

The Hilton Westchester hotel, located in the New York City suburb of Rye, NY, is just 10 minutes east of White Plains, NY in Westchester County and eight miles from Westchester County Airport... More

May

Cheapest weekend flights in May from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, May 16 Chicago (ORD) Westchester (HPN) US Airways $324
Earn $3.24
Return Mon, May 18 Westchester (HPN) Chicago (ORD) US Airways

Lowest roundtrip airfare in May from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, May 16 Chicago (ORD) Westchester (HPN) US Airways $324
Earn $3.24
Return Mon, May 18 Westchester (HPN) Chicago (ORD) US Airways

Best one-week trip in May from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, May 20 Chicago (ORD) Westchester (HPN) American Airlines $331
Earn $3.31
Return Wed, May 27 Westchester (HPN) Chicago (ORD) American Airlines
Back to menu Return to top

June

Cheapest weekend flights in June from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jun 4 Chicago (ORD) Westchester (HPN) American Airlines $351
Earn $3.51
Return Mon, Jun 8 Westchester (HPN) Chicago (ORD) American Airlines

Lowest roundtrip airfare in June from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Jun 10 Chicago (ORD) Westchester (HPN) US Airways $338
Earn $3.38
Return Tue, Jun 16 Westchester (HPN) Chicago (ORD) US Airways

Best one-week trip in June from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Jun 17 Chicago (ORD) Westchester (HPN) US Airways $338
Earn $3.38
Return Wed, Jun 24 Westchester (HPN) Chicago (ORD) US Airways
Back to menu Return to top

July

Cheapest weekend flights in July from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Jul 3 Chicago (ORD) Westchester (HPN) US Airways $363
Earn $3.63
Return Sun, Jul 5 Westchester (HPN) Chicago (ORD) US Airways

Lowest roundtrip airfare in July from Chicago to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jul 30 Chicago (ORD) Westchester (HPN) US Airways $361
Earn $3.61
Return Tue, Aug 4 Westchester (HPN) Chicago (ORD) US Airways
Back to menu Return to top

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 18m.
    • United Airlines flight 3938 (1:45 PM GMT, Embraer RJ135/RJ140/RJ145) is today's earliest available flight from Chicago to Westchester.
    • American Airlines flight 2932 (6:30 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 3938, Embraer RJ135/RJ140/RJ145) takes 2h 14m.
    • Today's longest direct flight from Chicago to Westchester (American Airlines flight 2932, Embraer RJ140) takes 2h 22m.
    • 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 Wed, Apr 22, 2015

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
United Airlines UA4213 ORD 7:45 AM HPN 10:54 AM ERJ 2hr 9min
American Airlines/American Airlines AA1853/AA4048 ORD 5:55 AM HPN 11:29 AM 321/CRJ 4hr 34min
American Airlines/US Airways AA1853/US4048 ORD 5:55 AM HPN 11:29 AM 321/CRJ 4hr 34min
US Airways/American Airlines US1853/AA4048 ORD 5:55 AM HPN 11:29 AM 321/CRJ 4hr 34min
US Airways/US Airways US1853/US4048 ORD 5:55 AM HPN 11:29 AM 321/CRJ 4hr 34min
Delta Air Lines/Delta Air Lines DL5410/DL3700 MDW 7:00 AM HPN 12:03 PM CR7/CRJ 4hr 3min
Delta Air Lines/Delta Air Lines DL2050/DL3700 ORD 7:00 AM HPN 12:03 PM 717/CRJ 4hr 3min
American Airlines AA3215 ORD 9:05 AM HPN 12:22 PM ERD 2hr 17min
US Airways US3215 ORD 9:05 AM HPN 12:22 PM ERD 2hr 17min
American Airlines/American Airlines AA1384/AA4809 ORD 7:10 AM HPN 1:22 PM 738/DH3 5hr 12min
American Airlines/US Airways AA1384/US4809 ORD 7:10 AM HPN 1:22 PM 738/DH8 5hr 12min
United Airlines/American Airlines UA3707/AA4809 ORD 7:30 AM HPN 1:22 PM CR7/DH3 4hr 52min
United Airlines/US Airways UA3707/US4809 ORD 7:30 AM HPN 1:22 PM CR7/DH8 4hr 52min