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Westchester to Chicago Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
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 Westchester to Chicago

Departure Arrival Travel dates Round-trip
HPN CHI Tue, Sep 23 - Thu, Sep 25 $343
HPN CHI Fri, Oct 10 - Tue, Oct 14 $377
HPN CHI Sat, Nov 22 - Mon, Nov 24 $396
HPN CHI Mon, Sep 29 - Sat, Oct 4 $537

Westchester and Chicago airports and terminals

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 HPN to CHI

    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

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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 HPN to ORD

    Terminal Carriers
    Terminal 1 United Airlines
    Terminal 2 United Airlines
    Terminal 3 American Airlines, US Airways
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Cheap flights from Westchester to Chicago

Sun Mon Tue Wed Thu Fri Sat
1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23
$343
24 25 26 27
28 29 30

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

September

Cheapest weekend flights in September from Westchester to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Sep 25 Westchester (HPN) Chicago (ORD) US Airways $421
Earn $4.21
Return Sun, Sep 28 Chicago (ORD) Westchester (HPN) US Airways

Lowest roundtrip airfare in September from Westchester to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Sep 23 Westchester (HPN) Chicago (ORD) Delta Air Lines $343
Earn $3.43
Return Thu, Sep 25 Chicago (ORD) Westchester (HPN) Delta Air Lines
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October

Cheapest weekend flights in October from Westchester to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Oct 17 Westchester (HPN) Chicago (ORD) United Airlines $377
Earn $3.77
Return Mon, Oct 20 Chicago (ORD) Westchester (HPN) United Airlines

Lowest roundtrip airfare in October from Westchester to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Oct 17 Westchester (HPN) Chicago (ORD) United Airlines $377
Earn $3.77
Return Mon, Oct 20 Chicago (ORD) Westchester (HPN) United Airlines
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November

Cheapest weekend flights in November from Westchester to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Nov 22 Westchester (HPN) Chicago (ORD) United Airlines $387
Earn $3.87
Return Mon, Nov 24 Chicago (ORD) Westchester (HPN) United Airlines

Lowest roundtrip airfare in November from Westchester to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Nov 3 Westchester (HPN) Chicago (ORD) US Airways $293
Earn $2.93
Return Tue, Nov 4 Chicago (ORD) Westchester (HPN) US Airways
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Flights to Chicago

Westchester County Airport

Individuals looking for cheap flights from Westchester can easily find travel information at orbitz.com. The site has a special search engine that searches a variety of airlines at once in order to find cheap deals for the budget traveler. The Westchester County Airport serves the residents of Westchester and the surrounding area and is located approximately eight miles from downtown, on Cooney Hill Road. Seven airlines service the Westchester County Airport, including AirTran, American, Delta, United, JetBlue, US Airways and Cape Air. Orbitz.com books flights on the majority of these airlines.

Parking at the Airport

A 24-hour parking garage is available for travelers leaving Westchester. Parking in the lots is charged by the hour or by the day, and there are no discounts available for long-term use. Parking is limited at the airport; once the parking garage has reached capacity, travelers can use the overflow lots. The airport offers free shuttle service to and from the overflow lots. Individuals should make arrangements for drop-off and pick-up prior to the flight.

Transportation to the Airport

The Westchester County Airport offers a variety of travel options to the airport. Travelers can book car rental services using orbitz.com. Car rental fees vary depending on the type of vehicle rented, the length of rental time and the number of miles driven. Limos can be rented by the hour, and taxi services are available for a metered rate plus a drop-off fee. The Bee-Line bus provides services to the airport for a flat fee, and the MTA railroad is also available. Fees for rail travel depend on the distance traveled.

Restaurants at Westchester County Airport

The Skytop Restaurant provides both breakfast menu items and coffee, and the Coffee Shop provides a variety of muffins, doughnuts and coffee items. Orbitz.com can help make finding cheap flights from Westchester easy.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Interesting facts about flights from Westchester to Chicago

    • 13 direct flights are operating from Westchester to Chicago today.
    • Today's average time for a direct flight is 2h 35m.
    • American Airlines flight 2817 (2:00 AM GMT, Embraer RJ140) is today's earliest available flight from Westchester to Chicago.
    • American Airlines flight 2854 (1:30 PM GMT, Embraer RJ140) is today's latest available flight from Westchester to Chicago.
    • Today's shortest direct flight from Westchester to Chicago (United Airlines flight 3259, Embraer RJ135/RJ140/RJ145) takes 2h 24m.
    • Today's longest direct flight from Westchester to Chicago (American Airlines flight 2817, Embraer RJ140) takes 2h 45m.
    • Flights from 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) to Midway Airport (MDW), O'Hare Airport (ORD) are available for this route.

Aircraft options between Westchester and Chicago

Equipment Carrier
Embraer RJ135/RJ140/RJ145 United Airlines
Embraer RJ140 American Airlines, US Airways