Compare fares, departure times, stops and baggage details for this route, then open the full search when you are ready to check current availability and complete booking.
HPNORDSat, 03 Oct
Fare checked before payment No hidden charges Transparent cancellation policy 24×7 booking support
Lowest fareUS$463American Airlines
Fastest2h 35mgate to gate
Options found62flights on this route
Find your flightHPN → ORD
Available Flights & Fares
Compare fares, timings and baggage. Pick the flight that suits your trip.
Prices in USD
62 flight options
Fares are checked again before payment.
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TownePlace Suites by Marriott Chicago Elgin-West Dundee
2185 Marriott Dr, 60118
Room availability is checked live
$81per night+ taxes if applicable
1 Night • 3 Star
3.0Very GoodLive availability
Hawthorn Suites by WY Chicago Schaumburg
1200 Bank Drive, 60173
Room availability is checked live
$85per night+ taxes if applicable
1 Night • 3 Star
3.0Very GoodLive availability
Hawthorn Suites by Wyndham Northbrook Wheeling
8000 Capitol Drive, 60090
Room availability is checked live
$86per night+ taxes if applicable
1 Night • 3 Star
4.0Very GoodLive availability
DoubleTree by Hilton Lisle Naperville
3003 Corporate West Dr, 60532
Room availability is checked live
$87per night+ taxes if applicable
1 Night • 4 Star
AA
American Airlines
AA-5431
11:02
2026-10-03
White Plains NY (HPN)Westchester County
7H :36 M
1 Stop
CLT
· 3h 21m Charlotte (CLT), United States
17:38
2026-10-03
CHICAGO (ORD)O Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 2 Pieces
$491
Flight DetailsHPN to ORD - 7H :36 M
Baggage InfoCheck-in 0 Pieces - Cabin 2 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Non Refundable
Fare Type
AirLine Private
1 Pieces 2 Pieces
$561
Flight DetailsHPN to ORD - 7H :36 M
Baggage InfoCheck-in 1 Pieces - Cabin 2 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
AA
American Airlines
AA-5180
13:42
2026-10-03
White Plains NY (HPN)Westchester County
4H :56 M
1 Stop
CLT
· 0h 43m Charlotte (CLT), United States
17:38
2026-10-03
CHICAGO (ORD)O Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 2 Pieces
$491
Flight DetailsHPN to ORD - 4H :56 M
Baggage InfoCheck-in 0 Pieces - Cabin 2 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Non Refundable
Fare Type
AirLine Private
1 Pieces 2 Pieces
$561
Flight DetailsHPN to ORD - 4H :56 M
Baggage InfoCheck-in 1 Pieces - Cabin 2 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
AA
American Airlines
AA-5180
13:42
2026-10-03
White Plains NY (HPN)Westchester County
6H :56 M
1 Stop
CLT
· 2h 40m Charlotte (CLT), United States
19:38
2026-10-03
CHICAGO (ORD)O Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 2 Pieces
$491
Flight DetailsHPN to ORD - 6H :56 M
Baggage InfoCheck-in 0 Pieces - Cabin 2 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Non Refundable
Fare Type
AirLine Private
1 Pieces 2 Pieces
$561
Flight DetailsHPN to ORD - 6H :56 M
Baggage InfoCheck-in 1 Pieces - Cabin 2 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
AA
American Airlines
AA-5070
18:58
2026-10-03
White Plains NY (HPN)Westchester County
6H :03 M
1 Stop
CLT
· 1h 48m Charlotte (CLT), United States
00:01
2026-10-04
CHICAGO (ORD)O Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 2 Pieces
$491
Flight DetailsHPN to ORD - 6H :03 M
Baggage InfoCheck-in 0 Pieces - Cabin 2 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Non Refundable
Fare Type
AirLine Private
1 Pieces 2 Pieces
$561
Flight DetailsHPN to ORD - 6H :03 M
Baggage InfoCheck-in 1 Pieces - Cabin 2 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
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Today's Airfare Highlights
Selected flight highlights for 03 Oct 2026.
Lowest fare$463American Airlines06:00
Earliest departure$463American Airlines06:00
Shortest duration$463American Airlines12:24
Night
00:00-05:59
No optionOpen full search for moreMorning
06:00-11:59
$463American Airlines at 06:00Afternoon
12:00-17:59
$463American Airlines at 12:24Evening
18:00-23:59
$473Delta Air Lines at 18:40
Departure & Arrival Airport Details
White Plains Ny (HPN)
Westchester County
USA
Chicago (ORD)
O Hare International
USA
Flights shown for 03 Oct 2026. View all flights opens the complete search result.
Smart travel dates
Holidays and peak dates for Chicago
Fares and hotel rates usually run higher around these dates. Booking earlier — or shifting a day or two — often costs less.
Busiest periods: Summer travel (15 Jun – 31 Aug), Holiday season (18 Dec – 02 Jan).
12OctColumbus DayMonday · in 30 daysPeak
12OctColumbus DayMonday · in 30 daysPeak
12OctIndigenous Peoples' DayMonday · in 30 daysPeak
11NovVeterans DayWednesday · in 60 days
26NovThanksgiving DayThursday · in 75 days
25DecChristmas DayFriday · in 104 days
Fixed-date national holidays. Festivals that follow the lunar calendar shift each year and are not listed here — check the exact date for your travel year.
Compare your journey
How to travel White Plains Ny to Chicago
Every option we can actually book for you, compared on price and journey time.
Connecting flight₹45,176Longer — includes a stop57 options
2 airlines operate this route.
Road distance and coach duration are approximate estimates from the air distance, not a timetable.
Airlines flying from White Plains Ny to Chicago
Compare fares, stops, baggage and refundability across the airlines flying this route.
AM
American Airlines Flights
from $46331 flights
Fares from
$463
Non-stop
5 in these results
Departures
31 — compare timings in the list above
DE
Delta Air Lines Flights
from $47331 flights
Fares from
$473
Non-stop
None in these results
Departures
31 — compare timings in the list above
Route Overview & Flight Facts
Fastest flight duration
2h 35m · American Airlines
First departure of the day
06:00 · American Airlines
Last departure of the day
18:58 · American Airlines
Options in this snapshot
62
Direct / non-stop options
5
Airport codes
White Plains Ny–HPN, Chicago–ORD
Fares and timings are indicative — the exact price is confirmed with the airline when you search.
Flight Schedule, Timings & Airfare Insights
Daily Flight Schedule & Travel Duration
Around 62 flights appear in the dated route snapshot, including 5 non-stop options. Departures run through the day — the first flight leaves around 06:00 and the last around 18:58. The fastest flight takes about 2h 35m.
Morning vs Evening Departure Fares
Lowest fare by departure window: Morning from $463, Afternoon from $463, Evening from $473. These observations do not predict the cheapest departure window on other dates.
Cheapest Airfare & Best Time to Book
Search your travel dates to compare current fares — prices update continuously with airline inventory.
One-Way vs Round-Trip Fare Comparison
Compare the complete cost and conditions of both options for your dates. A round-trip can have different fare and change rules from two one-way tickets. One booking may contain multiple airline PNRs; confirm baggage transfer and connection protection for separate tickets.
Online Web Check-In & Boarding Pass
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How to Book Cheap Flights on FlyX
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2
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3
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5
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Destination & City Travel Guide
About Chicago
Chicago, the most populous city in Illinois and the third most populous in the United States, is a bustling metropolis known for its iconic skyline, vibrant arts scene, and diverse neighborhoods. Often referred to as the Windy City, Chicago offers a blend of architectural marvels, cultural landmarks, and a dynamic urban atmosphere. From world-class museums to sandy beaches along Lake Michigan, Chicago is a city that captivates visitors with its charm and energy.
Read more about Chicago
Airports
Chicago is served by two major airports: • O'Hare International Airport (ORD) - Located approximately 18 miles northwest of downtown Chicago • Chicago Midway International Airport (MDW) - Situated about 10 miles southwest of the city center
Hotels and Restaurants
Chicago offers a wide range of accommodation options to suit every budget: • The Ritz-Carlton Chicago - Luxury hotel with stunning views of Lake Michigan • The Drake Hotel - Historic hotel with elegant rooms and top-notch service • Hotel Lincoln - Boutique hotel with a rooftop bar and quirky decor • HI Chicago Hostel - Budget-friendly option with modern amenities
When it comes to dining, Chicago is a food lover's paradise: • Alinea - Renowned for its innovative and artistic dishes • Lou Malnati's Pizzeria - Famous for its deep-dish pizza • Girl & the Goat - Popular spot for creative small plates • Portillo's - Iconic for its Chicago-style hot dogs
Transportation
Getting around Chicago is convenient with various transportation options: • Chicago Transit Authority (CTA) - Extensive network of buses and 'L' trains • Metra - Commuter rail system connecting the suburbs to the city • Taxis and Rideshares - Widely available across the city • Divvy Bikes - Bike-sharing program with numerous docking stations
Must-See Places
Chicago boasts numerous attractions that should not be missed: • Millennium Park - Home to the iconic Cloud Gate sculpture (The Bean) • The Art Institute of Chicago - Houses an impressive collection of artworks • Navy Pier - Entertainment hub with rides, restaurants, and shops • Willis Tower Skydeck - Offers breathtaking views from the 103rd floor • Museum Campus - Includes the Field Museum, Shedd Aquarium, and Adler Planetarium
Climate
Chicago experiences a continental climate with distinct seasons: • Winter (December to February) - Cold and snowy, ideal for winter sports • Spring (March to May) - Mild temperatures and blooming flowers • Summer (June to August) - Warm and humid, perfect for outdoor activities • Autumn (September to November) - Cool and crisp, great for sightseeing
The best time to visit Chicago is during late spring to early autumn when the weather is pleasant and outdoor events are in full swing. Whether you're exploring its architectural wonders, indulging in its culinary delights, or enjoying its vibrant cultural scene, Chicago promises an unforgettable experience.
Why Book Your Flight with FlyX?
Compare the available White Plains Ny to Chicago options by total price, stops, baggage and fare conditions. Search your dates for current availability, then review traveller details and the final price before paying.
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Frequently Asked Questions
Is it worth booking White Plains Ny to Chicago flights in advance?
There is no guaranteed cheapest booking window. Compare your planned dates early, check nearby dates and consider baggage, connection time and change conditions as well as price. Across the dates currently loaded for White Plains Ny to Chicago, Saturday shows the lowest fare at $463. That is an observed snapshot for these dates, not a rule that holds every week.
How far is White Plains Ny from Chicago by air?
The flying distance depends on the routing the airline selects. The live flight cards above show duration and stop details for each result.
Are there non-stop flights from HPN to ORD?
Yes. 5 non-stop flights are showing on White Plains Ny to Chicago for the dates currently loaded. Use the Stops filter to see only those.
Which airlines fly White Plains Ny to Chicago?
American Airlines and Delta Air Lines are showing on this route for the dates currently loaded. Fares, baggage allowance and refund rules differ by airline and by fare type, so compare the fare conditions and not only the headline price.
How long is the flight from White Plains Ny to Chicago?
The quickest non-stop White Plains Ny to Chicago flight currently loaded takes about 2h 35m. Across the non-stop options showing, block time ranges from 2h 35m to 2h 54m. Journeys with a stop take longer, since the total includes the layover.
What is the cheapest White Plains Ny to Chicago flight fare?
The lowest fare showing on White Plains Ny to Chicago for the dates currently loaded is $463. Fares on the same dates run up to $940, depending on airline, timing and fare type. Airline pricing moves continuously, so treat this as a dated observation rather than a fixed price.
What time do White Plains Ny to Chicago flights depart?
For the dates currently loaded the first departure is around 06:00 and the last is around 18:58, local time at White Plains Ny. Use the departure-time filter on the results above to narrow to a morning, afternoon or evening slot.
Why does the price change after clicking Book Now?
Airline seat inventory and fares change continuously. Selecting Book Now runs a live fare verification with the airline so the price you approve is the price you pay - if it has moved, you see the new figure before any payment.
Before you book this route
Check the airport codes HPN–ORD, local departure and arrival dates, and every connecting airport. Connections can have different document and baggage requirements from your final destination.
Where these fares come from
The fares, durations, stops and baggage shown here come from real airline search results for this route. They are examples for the dates on this page, not a full timetable and not a locked price — run a search to see what is available for your own dates.
Last checked .
Check official travel requirements
Confirm passport, visa and transit rules for your nationality and full itinerary with the relevant government and operating airline. IATA travel-document information explains why requirements vary.
The HPN to ORD cards above show selected flight options. Airline prices and seat availability can move quickly, so the final fare is rechecked in the booking flow.
Before you book
Compare nearby dates
The date strip opens the complete search result for the route and selected date.
Use filters
Shortlist by price, stops, departure time and refundable fare preference.
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Lowest White Plains Ny to Chicago airfare today, in 30 days and in 90 days
Cheapest Fare
Fare
Date
Airline
Departure
Lowest Airfare Today
$463
03/10/2026
American Airlines
06:00
Cheapest Airfare Within 30 Days
$453
12/10/2026
American Airlines
06:00
Cheapest Airfare Within 90 Days
$440
11/12/2026
American Airlines
06:00
Book White Plains Ny to Chicago Flight Tickets on FlyX
Planning to fly from White Plains Ny to Chicago? FlyX lets you compare flight rates, airline timings, layovers, and baggage allowances all in one simple list. From quick non-stop routes to flexible connecting options, finding and booking cheap air tickets has never been easier.
White Plains Ny to Chicago Flight Schedule and Timing
Around 62 flights operate on this route, providing plenty of choices for your travel window. The earliest morning flight departs from White Plains Ny at 06:00, while the last night flight leaves at 18:58. Flights depart from Westchester County and land at O Hare International.
Flight Route Details & Analysis
Flight Details
Information
Route
White Plains Ny to Chicago
Flight Duration
2H :35 M - 27H :36 M
Airport Codes
White Plains Ny - HPN, Chicago - ORD
Total Flights Available
62 flights (5 direct)
First Flight Departure
Departs at 06:00
Last Flight Departure
Departs at 18:58
Early Morning Flights (12 AM - 8 AM)
21 direct/indirect flights
Morning Flights (8 AM - 12 PM)
9 direct/indirect flights
Afternoon Flights (12 PM - 4 PM)
18 direct/indirect flights
Evening Flights (4 PM - 8 PM)
14 direct/indirect flights
Night Flights (8 PM - 12 AM)
0 direct/indirect flights
Airport Information & Terminals
HPN: White Plains airport. White Plains airport transfer should be matched to the exact hotel, suburb or meeting area. Rail can work well for light luggage, but late arrivals, winter weather and family baggage often make a direct cab or booked transfer easier.
ORD: Chicago airport system. Chicago flights commonly use O'Hare or Midway. O'Hare is a huge hub with rail access; Midway can be easier for some city-side trips. Winter weather and traffic should be part of the booking decision.
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Westchester County