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Cheap flights from Westchester County to Chicago (HPN - CHI)

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

How to find the cheapest flight from
Westchester County (HPN) to Chicago (CHI)

HPN - CHI
Price
$226 - $338
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 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 Westchester County to Chicago

One-way from

$114

One-way flight from Westchester County to Chicago

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 Westchester County to Chicago?

It’s generally more expensive to depart on a Monday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

How far in advance should I book a flight from Westchester County to Chicago?

To save on the cost of your flight from Westchester County to Chicago, book at least 20 days before your planned departure. Booking around this time can save you about 10% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $137 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $157.

What is the cheapest month to fly from Westchester County to Chicago?

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, April can be a great choice for travel to Chicago. Flights to Chicago from Westchester County in April are about $135 on average during April, but can be found for as low as $33.

When is the cheapest time to fly from Westchester County to Chicago (HPN - CHI)?

Unlike in the afternoon, when flights are generally more expensive, you can save up to 42% on flights from Westchester County to Chicago by exploring options for tickets in the evening.

Cheap flights from Westchester County to Chicago in January, February 2021

The best prices found for HPN to CHI flights for January, February
18 Feb - 22 Feb
$202pp
HPN
White Plains Westchester County
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HPN
White Plains Westchester County
6 Feb - 20 Feb
$222pp
HPN
White Plains Westchester County
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HPN
White Plains Westchester County
5 Feb - 8 Feb
$224pp
HPN
White Plains Westchester County
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HPN
White Plains Westchester County

Westchester County to Chicago 2021 flight deals

Cheap flights to Chicago from Westchester County found for this year
16 Mar - 30 Mar
$187pp
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
16 Mar - 30 Mar
$195pp
HPN
White Plains Westchester County
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
HPN
White Plains Westchester County
18 Feb - 22 Feb
$202pp
HPN
White Plains Westchester County
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HPN
White Plains Westchester County

Non-stop flights to Chicago from Westchester County

Save time with Westchester County to Chicago direct flight deals
16 Mar - 30 Mar
$187pp
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
5 Mar - 8 Mar
$207pp
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
9 Apr - 11 Apr
$227pp
HPN
White Plains Westchester County
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
HPN
White Plains Westchester County

Last minute flights from Westchester County to Chicago

Late deals on round-trip flights to Chicago from Westchester County, departing today and this week
3 Feb - 8 Feb
$249pp
HPN
White Plains Westchester County
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HPN
White Plains Westchester County
1 Feb - 3 Feb
$255pp
HPN
White Plains Westchester County
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
HPN
White Plains Westchester County
3 Feb - 6 Feb
$256pp
HPN
White Plains Westchester County
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HPN
White Plains Westchester County

One-way flights to Chicago from Westchester County

The cheapest one-way flights from Westchester County to Chicago
1:07 pm - 2:50 pm
United Airlines
Nonstop
2h 43m
HPN - ORD
United Airlines
$114
United
3:15 am - 12:20 pm
JetBlue
1 Stop
10h 05m
HPN - ORD
JetBlue
1:46 am - 4:55 am
Delta
1 Stop
4h 09m
HPN - MDW
Delta
$178
Delta

Related info for your journey

Useful info, stats and facts about Westchester County to Chicago flights.

Flight FAQs

From Westchester County to Chicago

Are flight prices decreasing from Bridgeport to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Bridgeport and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from White Plains Westchester County to Chicago to control the spread of COVID-19?

New policies can now be found on Delta to help keep travelers safe while flying. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially distanced seating (for a limited time) will work towards keeping travelers safer while flying from White Plains Westchester County to Chicago. Policies will vary by airline.

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 Westchester County to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from Westchester County to Chicago for under $200. The cheapest flight booked recently is on United Airlines for just $187, but on average you can expect to pay $228.

Are there nonstop flights from Westchester County to Chicago for under $200 on Cheapflights?

Cheapflights has at least 5 direct flights from Westchester County to Chicago under $200. A good price for a nonstop flight from Westchester County to Chicago is less than $288.

Are there last-minute flights available from Westchester County to Chicago for under $300?

There are currently 18+ open flights from Westchester County to Chicago within the next 7 days for less than $300.

Is Bridgeport weather warmer or cooler than Chicago?

With an average temperature of 84 °F, peak weather can be found in July. As a traveler, expect to see changes in flight prices during that period. The temperatures in Chicago are the same as in Bridgeport.

How long is the flight from Westchester County to Chicago?

For as low as $235, American Airlines can have you in Chicago from Westchester County in 2h 31m. Both multi-stop and nonstop flights can be found to your destination and back.

What are the cheapest airlines flying from Westchester County to Chicago round-trip?

Our cheapest airline available from Westchester County to Chicago is United Airlines. Our recent data shows that you can find tickets from as low as $187 on this airline. Additional options worth looking into are American Airlines and Delta, starting at $195 and $209 round-trip. United Airlines is currently priced 35% below the average price you’ll pay for this route.

What are the cheapest airlines to fly from Westchester County to Chicago one-way?

The cheapest airlines for a one-way flight from Westchester County to Chicago are United Airlines ($94), American Airlines ($101), and Delta ($103).

Alternative routes for Westchester County to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Westchester County to Chicago
Flight duration
2h 27m
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing White Plains

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 4 airlines flying from Westchester County to Chicago

The chart below displays the airlines Cheapflights users traveling from Westchester County 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%
United Airlines
$102 $332 No cancel fee 69%
Delta
$98 $347 No cancel fee N/A
American Airlines
$169 $349 No cancel fee 71%
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