Cheap flights from White Plains to Chicago (HPN - CHI)

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The best prices from White Plains Westchester County to Chicago are usually found in January or July, booked 58 days in advance, depart on a Tuesday or Saturday and return on a Saturday

How to find the cheapest flight from
White Plains (HPN) to Chicago (CHI)

All the information you need to plan the best HPN to CHI flight in 2021: compare White Plains to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
HPN - CHI
Price
$226 - $338
CHI
Temperature
23 - 73.4 °F
CHI
Precipitation
1.7 - 4.9 inches

Popular in

October

High demand for flights, 15% potential price rise

Cheapest in

January

Best time to find cheap flights, 21% potential price drop

Round-trip from

$226

From White Plains Westchester County to Chicago (CHI)

One-way from

$98

One-way flight from White Plains Westchester County to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from White Plains to Chicago?

Users have found that flying from White Plains to Chicago on a Saturday typically leans towards higher prices. However, this doesn’t mean you still can’t find a deal. Flexibility with other aspects of your flight can still land a great price for your trip.

What is the cheapest month to fly from White Plains to Chicago?

August can be a great time to fly to Chicago from White Plains with a flight ticket averaging about $182. Cheapflights users have found deals in the month of August for as cheap as $64. The most expensive prices can be found in the month of December.

When is the cheapest time to fly from White Plains to Chicago (HPN - CHI)?

It’s optimal to fly from White Plains to Chicago at noon. By choosing this option you can save up to 35% on the cost of your flight, compared to a flight in the afternoon.

How far in advance should I book a flight from White Plains to Chicago?

Travelers have found it’s best to book a flight 20 days in advance to save up to 48% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 20 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from White Plains to Chicago 1-2 weeks in advance for as low as $213, or $293 for flights within the next 24 hours.

Cheap flights from White Plains to Chicago in October, November 2021

The best prices found for HPN to CHI flights for October, November
6 Nov - 7 Nov
$173pp
HPN
White Plains Westchester County
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
HPN
White Plains Westchester County
5 Nov - 6 Nov
$183pp
HPN
White Plains Westchester County
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
HPN
White Plains Westchester County
6 Nov - 6 Nov
$187pp
HPN
White Plains Westchester County
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
HPN
White Plains Westchester County

White Plains Westchester County to Chicago 2021 flight deals

Cheap flights to Chicago from White Plains found for this year
6 Nov - 7 Nov
$173pp
HPN
White Plains Westchester County
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
HPN
White Plains Westchester County
10 Dec - 11 Dec
$183pp
HPN
White Plains Westchester County
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
HPN
White Plains Westchester County
6 Nov - 6 Nov
$187pp
HPN
White Plains Westchester County
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
HPN
White Plains Westchester County

Non-stop flights to Chicago from White Plains

Save time with White Plains to Chicago direct flight deals
14 Jan - 17 Jan
$189pp
HPN
White Plains Westchester County
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
HPN
White Plains Westchester County
2 Nov - 11 Nov
$194pp
HPN
White Plains Westchester County
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
HPN
White Plains Westchester County
8 Nov - 10 Nov
$199pp
HPN
White Plains Westchester County
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
HPN
White Plains Westchester County

Last minute flights from White Plains to Chicago

Late deals on round-trip flights to Chicago from White Plains, departing today and this week
29 Oct - 1 Nov
$210pp
HPN
White Plains Westchester County
JetBlue
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
JetBlue
 
1 STOP
HPN
White Plains Westchester County
29 Oct - 1 Nov
$214pp
HPN
White Plains Westchester County
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
HPN
White Plains Westchester County
29 Oct - 31 Oct
$218pp
HPN
White Plains Westchester County
JetBlue
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
JetBlue
 
1 STOP
HPN
White Plains Westchester County

One-way flights to Chicago from White Plains

The cheapest one-way flights from White Plains to Chicago
2:10 am - 2:05 pm
Multiple Airlines
1 Stop
12h 55m
HPN - ORD
Multiple Airlines
$98
Priceline
11:45 am - 6:58 pm
JetBlue
1 Stop
8h 13m
HPN - ORD
JetBlue
2:00 am - 6:58 am
Delta
1 Stop
5h 58m
HPN - MDW
Delta
$159
Delta

Related info for your journey

Useful info, stats and facts about <span class="emphasized">White Plains</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From White Plains to Chicago

What airport do you fly from for flights from White Plains to Chicago?

Most people fly from White Plains Westchester County (HPN) if they book a flight from White Plains to Chicago. On average, Westchester County has 6 outbound flights to Chicago per day from 5 airlines. White Plains Westchester County is conveniently located just 3.7 mi from White Plains’s city center.

Which airlines flying from White Plains Westchester County to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from White Plains Westchester County to Chicago have new flexible policies in place due to COVID-19. American Airlines, United Airlines, and Delta are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like American Airlines with this kind of flexibility.

Can I find flights from White Plains to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from White Plains to Chicago for under $200. The cheapest flight booked recently is on American Airlines for just $173, but on average you can expect to pay $197.

Are there nonstop flights from White Plains to Chicago for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from White Plains to Chicago under $200. A good price for a nonstop flight from White Plains to Chicago is less than $244.

Are there last-minute flights available from White Plains to Chicago for under $300?

There are currently 20+ open flights from White Plains to Chicago within the next 7 days for less than $300.

What are the cheapest airlines flying from White Plains to Chicago round-trip?

Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $173. Additional round-trip tickets that might be worth considering are offered by United Airlines and Delta, with the lowest prices starting at $189 and $207, respectively. Users have found that American Airlines is 39% cheaper than the other options available to this destination.

What are the cheapest airlines to fly from White Plains to Chicago one-way?

One-way options have recently been found by users for as low as $96 on JetBlue. Other airlines that offer cheap prices include American Airlines from $100 and Major Airline from $105 one-way.

What are the most popular airlines that fly from White Plains to Chicago?

The most popular airlines flying from White Plains to Chicago are Major Airline, American Airlines and Delta. Something to consider prior to booking your flight.

What are the most reliable airlines from White Plains to Chicago?

Before booking your flight to Chicago from White Plains, check out the most reliable airlines to get you to your destination on time: SkyWest Airlines (94%), American Airlines (94%), Alaska Airlines( 92%).

What are the cheapest flights from White Plains to Chicago?

The cheapest flight price from White Plains to Chicago is $90. On average you can expect to pay $325. The most popular route, (White Plains Westchester County - Chicago O'Hare Intl), can usually be booked for $189.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from White Plains?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from White Plains Westchester County need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from White Plains Westchester County must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from White Plains Westchester County are not required to quarantine after entering Chicago.

Do I need a test to fly back to White Plains from Chicago?

Returning to White Plains Westchester County from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to White Plains Westchester County.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering White Plains Westchester County.

Hide COVID Travel Restrictions for Chicago, IL

Alternative routes for White Plains to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from White Plains to Chicago.
Flight duration from HPN to Chicago
2h 26m
Average temperature for October in Chicago
64.4 °F
Avg rainfall for October in Chicago
2.6 ″

Airports servicing White Plains

White Plains Westchester County (HPN)

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Top 4 airlines flying from White Plains Westchester County to Chicago

The chart below displays the airlines Cheapflights users traveling from White Plains to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Spirit Airlines
$63 $195 No cancel fee 65%
Delta
$98 $347 No cancel fee N/A
United Airlines
$102 $332 No cancel fee 69%
American Airlines
$169 $349 No cancel fee 71%

Hourly flight availability from White Plains to Chicago

See what time of day planes typically take off from White Plains towards Chicago.
Afternoon Noon to 6 PM 44% of HPN to CHI departures
Morning 6 AM to noon 41% of HPN to CHI departures
Early morning Midnight to 6 AM 15% of HPN to CHI departures
Evening 6 PM to midnight 0% of HPN to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from White Plains to Chicago
See how many times per day planes take to the skies headed from White Plains to Chicago.
Sunday
5 daily flights
Monday
7 daily flights
Tuesday
7 daily flights
Wednesday
7 daily flights
Thursday
7 daily flights
Friday
7 daily flights
Saturday
7 daily flights
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