Find cheap flight tickets from White Plains (HPN) to Chicago (ORD). Cheapest fare starts from $279.
White Plains
HPN
→
Chicago
ORD
11/05/2025 – 11/12/2025
Cheap flight deals from White Plains to Chicago
Average price start from:
i
$249
Round-trip flights from White Plains to Chicago starting at $249. Book now for the best deals!
One-way from:
i
$152
One-way flights from White Plains to Chicago starting at $152. Great for flexible travel!
Cheapest day:
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Wednesday
Wednesday is the cheapest day to fly from White Plains to Chicago. Save more by booking on this day!
Cheapest In:
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$53
Sep 2025
Sep 2025 is the cheapest month to fly from White Plains to Chicago with prices starting at $53.
Find flight deals from White Plains to Chicago
Cheapest flights from White Plains to Chicago
ONEWAY FLIGHTS
LAST MINUTE
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Explore the cheapest oneway flights from White Plains to Chicago spotted daily.
HPN
White Plains
HPN - White Plains • 2025-11-05 • 09:00
Unknown
60 min
ORD
Unknown City
$152
Non-stop • 60 min
HPN
White Plains
HPN - White Plains • 2025-11-05 • 09:00
Unknown
60 min
MKE
Unknown City
$155
Non-stop • 60 min
HPN
White Plains
HPN - White Plains • 2025-11-05 • 09:00
Unknown
60 min
ORD
Unknown City
$179
Non-stop • 60 min
HPN
White Plains
HPN - White Plains • 2025-11-05 • 09:00
Unknown
60 min
ATW
Unknown City
$201
Non-stop • 60 min
HPN
White Plains
HPN - White Plains • 2025-11-05 • 09:00
Unknown
60 min
MSP
Unknown City
$244
Non-stop • 60 min
HPN
White Plains
HPN - White Plains • 2025-11-05 • 09:00
Unknown
60 min
GRB
Unknown City
$250
Non-stop • 60 min
HPN
White Plains
HPN - White Plains • 2025-11-05 • 09:00
Unknown
60 min
MKE
Unknown City
$260
Non-stop • 60 min
HPN
White Plains
HPN - White Plains • 2025-11-05 • 09:00
Unknown
60 min
MSN
Unknown City
$279
Non-stop • 60 min
HPN
White Plains
HPN - White Plains • 2025-11-05 • 09:00
Unknown
60 min
MSP
Unknown City
$280
Non-stop • 60 min
HPN
White Plains
HPN - White Plains • 2025-11-05 • 09:00
Unknown
60 min
MSN
Unknown City
$295
Non-stop • 60 min
HPN
White Plains
HPN - White Plains • 2025-11-05 • 09:00
Unknown
60 min
ORD
Unknown City
$303
Non-stop • 60 min
HPN
White Plains
HPN - White Plains • 2025-11-05 • 09:00
Unknown
60 min
MSN
Unknown City
$309
Non-stop • 60 min
Price Trends & Analysis
Monthly Price Trends
Lowest fares from White Plains to Chicago typically available in April.
Weather & Climate Information
Temperature
Chicago experiences a humid continental climate, with winter temperatures averaging 20°F to 30°F and summer temperatures ranging from 70°F to 85°F. The best times for comfortable travel are late spring (May to June) and early fall (September to October), when temperatures are mild and rainfall is relatively low.
Rainfall
The best time to visit Chicago is from late spring to early fall, particularly May to September, when the weather is warm and pleasant. During this period, you can enjoy vibrant local events like the Chicago Air and Water Show and the Chicago Blues Festival, making it an ideal time for sightseeing and experiencing the city's culture.
Airlines at Chicago
Traveling from White Plains to Chicago has never been more convenient, thanks to several reputable airlines offering seamless connectivity between these vibrant cities. Airlines such as Delta Air Lines, American Airlines, Breeze Airways provide regular flights, ensuring travelers have flexible options to suit their schedules.
Typically, the flight duration is around 10-15 hours, depending on layovers and the chosen route. Most flights from White Plains to Chicago include one stopover, often in major hubs, allowing for a comfortable transition. For those seeking to explore Chicago, booking with these airlines ensures a smooth travel experience, complete with modern amenities and excellent service.
Places to Visit in Chicago
Chicago, the Windy City, captivates with its stunning skyline and vibrant cultural tapestry, blending architectural marvels like the Willis Tower with the rich history of jazz and blues. Visitors can explore world-class museums, savor deep-dish pizza, and stroll along the picturesque shores of Lake Michigan. From the bustling energy of Millennium Park to the historic charm of the Chicago Riverwalk, every corner reveals a unique story, inviting travelers to immerse themselves in an unforgettable urban adventure.
About Chicago
Explore the wonders of Chicago on your journey from White Plains. This remarkable destination blends cultural treasures with modern amenities, creating an enriching travel experience. Consider visiting during off-peak seasons for better value and fewer crowds.
Airlines Flying from White Plains to Chicago
Traveling from White Plains to Chicago has never been more convenient, thanks to several reputable airlines offering seamless connectivity between these vibrant cities. Airlines such as Delta Air Lines, American Airlines, Breeze Airways provide regular flights, ensuring travelers have flexible options to suit their schedules.
Typically, the flight duration is around 10-15 hours, depending on layovers and the chosen route. Most flights from White Plains to Chicago include one stopover, often in major hubs, allowing for a comfortable transition. For those seeking to explore Chicago, booking with these airlines ensures a smooth travel experience, complete with modern amenities and excellent service.
Hotels in Chicago
When staying in Chicago, look for hotels with easy access to ORD Airport. Most properties provide shuttle services for seamless airport transfers.
About Chicago
Explore the wonders of Chicago on your journey from White Plains. This remarkable destination blends cultural treasures with modern amenities, creating an enriching travel experience. Consider visiting during off-peak seasons for better value and fewer crowds.
Places to Visit in Chicago
Chicago, the Windy City, captivates with its stunning skyline and vibrant cultural tapestry, blending architectural marvels like the Willis Tower with the rich history of jazz and blues. Visitors can explore world-class museums, savor deep-dish pizza, and stroll along the picturesque shores of Lake Michigan. From the bustling energy of Millennium Park to the historic charm of the Chicago Riverwalk, every corner reveals a unique story, inviting travelers to immerse themselves in an unforgettable urban adventure.
Hotels in Chicago
When staying in Chicago, look for hotels with easy access to ORD Airport. Most properties provide shuttle services for seamless airport transfers.
Airlines Flying from White Plains to Chicago
Traveling from White Plains to Chicago has never been more convenient, thanks to several reputable airlines offering seamless connectivity between these vibrant cities. Airlines such as Delta Air Lines, American Airlines, Breeze Airways provide regular flights, ensuring travelers have flexible options to suit their schedules.
Typically, the flight duration is around 10-15 hours, depending on layovers and the chosen route. Most flights from White Plains to Chicago include one stopover, often in major hubs, allowing for a comfortable transition. For those seeking to explore Chicago, booking with these airlines ensures a smooth travel experience, complete with modern amenities and excellent service.
Frequently Asked Questions
How much does it cost to fly from White Plains to Chicago?
Flight prices start from $152 for this route. Save more by booking during April and choosing Wednesday departures.
What's the flight duration from White Plains to Chicago?
The typical flight time is approximately 10-15 hours, with most routes featuring one stopover for better pricing and convenience.
What airlines serve the White Plains to Chicago route?
Several airlines operate flights including Delta Air Lines, American Airlines, Breeze Airways. Compare schedules and prices to find the best option for your travel needs.
When should I book my flight for the best price?
For optimal savings, book 2-3 months ahead and consider traveling during April when demand is lower.
Where can I stay near ORD Airport?
There are several hotels near ORD Airport with convenient shuttle services. Many offer comfortable accommodations for both business and leisure travelers.
What makes Chicago worth visiting?
Chicago combines rich cultural heritage with modern attractions. Visit during pleasant weather months to experience the city at its best.
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