Popular airlines from Westchester County Airport (HPN) to Chicago O'Hare Intl. Airport (ORD)
DeltaDelta
American AirlinesAmerican Airlines
JetBlue AirwaysJetBlue Airways
- Plan, book, fly with confidence
- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 30% on select hotels after you book a flight*
Cheap Flights from White Plains to Chicago (HPN-ORD)
Prices were available within the past 7 days and start at $130 for one-way flights and $283 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Frequently asked questions
Travel information
Travel information
Origin airport | Westchester County |
Destination airport | O'Hare Intl. |
Airlines serving | American Airlines, Delta, JetBlue Airways |
Roundtrip price | $283 |
Distance | 736 mi |
Book with confidence
Book with confidence
The cheapest times to fly from White Plains to Chicago
On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from White Plains to Chicago are during the month of May. You can find some of the cheapest flights from White Plains to Chicago with Expedia's search tool and vast selection of airlines.
The best time to book a flight from White Plains to Chicago
Sunday is one of the best days to book for cheap flights from White Plains to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.
How to find cheap round-trip tickets from White Plains to Chicago
Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from White Plains to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $130 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.
Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap White Plains to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.
You could also save big by booking one of Expedia's vacation packages. Bundling together your White Plains to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.
*Terms apply.
Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.
Be inspired and discover more with Expedia
Be inspired and discover more with Expedia
Flights
- Flights from Chicago (ORD) to Orlando (MCO)
- Flights from New York (JFK) to Orlando (MCO)
- Flights from White Plains (HPN) to Raleigh (RDU)
- Flights from San Francisco (SFO) to New York (JFK)
- Flights from Los Angeles (LAX) to New York (JFK)
- Flights from Seattle (SEA) to New York (JFK)
- Flights from Chicago (ORD) to Phoenix (PHX)
- Flights from New York (JFK) to Honolulu (HNL)
- Flights from New York (JFK) to Rome (FCO)
- Flights from Chicago (ORD) to Denver (DEN)
- Flights from Chicago (ORD) to Atlanta (ATL)
- Flights from Chicago (ORD) to San Francisco (SFO)
- Flights from New York (JFK) to San Francisco (SFO)
- Flights from White Plains (HPN) to Fort Lauderdale (FLL)
- Flights from Phoenix (PHX) to Chicago (ORD)
- Flights from Fort Lauderdale (FLL) to Chicago (ORD)
- Flights from Miami (MIA) to Chicago (ORD)
- Flights from Dallas (DFW) to Chicago (ORD)
- Flights from Denver (DEN) to Chicago (ORD)
- Flights from Atlanta (ATL) to Chicago (ORD)
- Flights from Boston (BOS) to Chicago (ORD)
- Flights from Tampa (TPA) to Chicago (ORD)
- Flights from Los Angeles (LAX) to Chicago (ORD)
- Flights from Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
- Flights from Dallas (DAL) to Chicago (ORD)
- Flights from New York (LGA) to Chicago (ORD)
- Flights from Charlotte (CLT) to Chicago (ORD)
- Flights from New York (JFK) to Chicago (ORD)
- Flights from Chicago (ORD) to Tampa (TPA)
- Flights from White Plains (HPN) to Tampa (TPA)
- Flights from White Plains (HPN) to Charleston (CHS)
- Flights from White Plains (HPN) to Miami (MIA)
- Flights from New York (LGA) to Miami (MIA)
- Flights from Chicago (ORD) to Miami (MIA)
- Flights from Chicago (ORD) to Las Vegas (LAS)
- Flights from New York (JFK) to Punta Cana (PUJ)
- Flights from Chicago (ORD) to Dallas (DFW)
- Flights from New York (JFK) to San Juan (SJU)
- Flights from White Plains (HPN) to Detroit (DTW)
- Flights from Chicago (ORD) to Seattle (SEA)
- Flights from New York (JFK) to London (LHR)
- Flights from White Plains (HPN) to Myrtle Beach (MYR)
- Flights from New York (JFK) to Tokyo (NRT)
- Flights from White Plains (HPN) to Charlotte (CLT)
- Flights from White Plains (HPN) to Sarasota (SRQ)
- Flights from New York (JFK) to Paris (CDG)
- Flights from White Plains (HPN) to Vero Beach (VRB)
- Flights from Chicago (ORD) to Los Angeles (LAX)
- Flights from White Plains (HPN) to Los Angeles (LAX)
- Flights from New York (JFK) to Los Angeles (LAX)
- Flights from White Plains (HPN) to Washington (DCA)
- Flights from Chicago (ORD) to New York (LGA)
- JetBlue Airways White Plains (HPN) to West Palm Beach (PBI) flights
- JetBlue Airways White Plains (HPN) to Fort Lauderdale (FLL) flights
- Spirit Airlines New York (LGA) to Chicago (ORD) flights
- JetBlue Airways Boston (BOS) to Chicago (ORD) flights
- JetBlue Airways New York (JFK) to Chicago (ORD) flights
- Spirit Airlines Charlotte (CLT) to Chicago (ORD) flights
- Alaska Airlines Phoenix (PHX) to Chicago (ORD) flights
- Spirit Airlines Tampa (TPA) to Chicago (ORD) flights
- Frontier Airlines Denver (DEN) to Chicago (ORD) flights
- Alaska Airlines Los Angeles (LAX) to Chicago (ORD) flights
- American Airlines Miami (MIA) to Chicago (ORD) flights
- JetBlue Airways Fort Lauderdale (FLL) to Chicago (ORD) flights
- JetBlue Airways White Plains (HPN) to Tampa (TPA) flights
- Delta White Plains (HPN) to Miami (MIA) flights
- Delta White Plains (HPN) to Detroit (DTW) flights
- Delta White Plains (HPN) to Myrtle Beach (MYR) flights
- Delta White Plains (HPN) to Sarasota (SRQ) flights
- American Airlines White Plains (HPN) to Washington (DCA) flights
- JetBlue Airways White Plains (HPN) to Fort Myers (RSW) flights
- Flights to Chicago
- Flights to San Diego
- Flights to Nashville
- Flights to San Francisco
- Flights to Gatlinburg
- Flights to Las Vegas
- Flights to Miami
- Flights to Fort Lauderdale
- Flights to Key West
- Flights to Orlando
- Flights to Boston
- Flights to Pigeon Forge
- Flights to Atlanta
- Flights to Houston
- Flights to Los Angeles
- Flights to Honolulu
- Flights to San Antonio
- Flights to Washington
- Flights to New Orleans
- Flights to New York
- Alaska Airlines
- Delta
- LATAM Airlines Group
- KLM
- WestJet
- Qatar Airways
- Aeromexico
- JetBlue Airways
- American Airlines
- Cape Air
- Breeze Airways
- Virgin Atlantic
- Korean Air
- Azul
- Flights from John F. Kennedy Intl.
- Flights from Republic
- Flights from Newark Liberty Intl. Airport
- Flights from Igor I. Sikorsky Memorial
- Flights from Essex County
- Flights from Stewart Intl.
- Flights from MacArthur
- Flights from Danbury Municipal
- Flights from Teterboro
- Flights from LaGuardia