Cheap flights from Westchester County to Chicago

Flights overview

Useful information for finding cheap flights from Westchester County to Chicago and booking your next trip
Cheapest round-trip flights $307
American 2 stops 13 hr Sat, Jun 6 — Sun, Jun 7
The cheapest round-trip flight from Westchester County to Chicago is currently $307
Cheapest one-way flight $183
American 2 stops 12 hr Wed, May 27
The cheapest one-way flight from Westchester County to Chicago is currently $183
Cheapest nonstop flights $439
American Nonstop 3 hr Fri, Jul 3 — Sun, Jul 5
The cheapest nonstop round-trip flight from Westchester County to Chicago is currently $439
Last-minute weekend getaway $337
American 2 stops 14 hr Sat, May 9 — Sun, May 10
The cheapest last-minute weekend getaway from Westchester County to Chicago is currently $337
Cheapest business class flights $740
American Nonstop 3 hr Fri, Jul 3 — Sun, Jul 5
The cheapest business class round-trip flight from Westchester County to Chicago is currently $740
Fastest flight 2 hr 33 min The fastest nonstop flight from Westchester County to Chicago takes 2 hr 33 min
Nonstop flights Some days There are direct flights on this route 6 days a week: Mon, Tue, Thu, Fri, Sat, Sun.

When is the cheapest time to fly?

The cheapest month to fly from Westchester County to Chicago is typically September. The most expensive month to fly is typically June.
September
Cheapest
Typical prices: $225–495
June
Most expensive
Typical prices: $355–495

Popular airlines from Westchester County to Chicago

  • American
    Nonstop
    from $307
    Typical price: $310–480
    21 weekly nonstop flights
    HPN - ORD Every Mon, Tue, Thu, Fri, Sat, Sun
    635 weekly connecting flights
    HPN - ORD Every day
  • Delta
    from $459
    Typical price: $405–600
    316 weekly connecting flights
    HPN - MDW, ORD Every Mon, Thu, Fri, Sat, Sun

Popular airports near Westchester County

  • John F. Kennedy International Airport (JFK)
    New York United States 57 min 33 mi
  • LaGuardia Airport (LGA)
    New York United States 45 min 24 mi
  • Westchester County Airport (HPN)
    Westchester County United States 22 min 6 mi
  • Newark Liberty International Airport (EWR)
    Newark United States 59 min 35 mi

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 23 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from Westchester County to Chicago

The cheapest flights from Westchester County to Chicago are usually in September. Typical ticket prices in September range from $225 to $495.
The cheapest round-trip flight from Westchester County to Chicago recently found on Google Flights was with American from $307. The cheapest one-way flight was with American from $183.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest American flight from Westchester County to Chicago is $307, flying from Jun 6 to Jun 7.
  • The cheapest Delta flight from Westchester County to Chicago is $459, flying from Jul 3 to Jul 5.
The cheapest round-trip flight from Westchester County to Chicago starts at $307 from Sat, Jun 6 to Sun, Jun 7. The cheapest one-way flight starts at $183 and departs on Wed, May 27.
2 hr 33 min is the shortest flight time from Westchester County to Chicago.
Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
It's easy to use Google Flights to find the cheapest days to fly from Westchester County to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from Westchester County to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Westchester County to Chicago.

In terms of nonstop flights, American is the most popular. American offers 21 nonstop flights and 635 connecting flights per week. American flies from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD) .

Another popular airline flying from Westchester County to Chicago is:
  • Delta offers 316 connecting flights per week. Delta flies from Westchester County Airport (HPN) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
The number of connecting flights refers to distinct flights with at least one stop between Westchester County and Chicago.
The cheapest round-trip flight from Westchester County to Chicago recently found on Google Flights was with American from $307. The cheapest one-way flight was with American from $183.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest American flight from Westchester County to Chicago is $307, flying from Jun 6 to Jun 7.
  • The cheapest Delta flight from Westchester County to Chicago is $459, flying from Jul 3 to Jul 5.
American flies direct from Westchester County to Chicago.
  • There are 21 American direct flights from Westchester County to Chicago per week. Flights are available on Monday, Tuesday, Thursday, Friday, Saturday and Sunday.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between Westchester County and Chicago at price $337 is offered by American from Sat, May 9 to Sun, May 10.
American flies direct from Westchester County to Chicago.
  • There are 21 American direct flights from Westchester County to Chicago per week. Flights are available on Monday, Tuesday, Thursday, Friday, Saturday and Sunday.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
Direct flights from Westchester County to Chicago are only available on Monday, Tuesday, Thursday, Friday, Saturday and Sunday.
The cheapest direct (nonstop) round-trip flights between Westchester County and Chicago start at $439 from Fri, Jul 3 to Sun, Jul 5 with American.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Westchester County to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between Westchester County and Chicago start at $740 from Fri, Jul 3 to Sun, Jul 5 with American.
The cheapest economy class round-trip flights between Westchester County and Chicago start at $307 from Sat, Jun 6 to Sun, Jun 7.
To book business class trips from Westchester County to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between Westchester County and Chicago starts at $337 from Sat, May 9 to Sun, May 10 with American.
The cheapest last-minute deal between Westchester County and Chicago at price $337 is offered by American from Sat, May 9 to Sun, May 10.
To find last-minute flight deals from Westchester County to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

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Popular trips from Westchester County

  1. Paris
    $848
    Sep 10 — Sep 14
    2 stops 15 hr 16 min American, British Airways
  2. London
    $859
    Oct 1 — Oct 5
    2 stops 11 hr 41 min American, British Airways
  3. Charleston
    $128
    Sep 12 — Sep 14
    Nonstop 2 hr 13 min Breeze
  4. Los Angeles
    $359
    Aug 15 — Aug 17
    2 stops 9 hr 21 min American

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