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 Saturday and return on a Saturday

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

All the information you need to plan the best HPN to CHI flight in 2021: compare Westchester County to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
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

$127

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 35% on flights from Westchester County to Chicago by exploring options for tickets at noon.

Cheap flights from Westchester County to Chicago in May, June 2021

The best prices found for HPN to CHI flights for May, June
12 Jun - 19 Jun
$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
25 Jun - 29 Jun
$197pp
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
11 Jun - 12 Jun
$204pp
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

Westchester County to Chicago 2021 flight deals

Cheap flights to Chicago from Westchester County found for this year
9 Oct - 10 Oct
$125pp
HPN
White Plains Westchester County
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HPN
White Plains Westchester County
14 Sep - 19 Sep
$126pp
HPN
White Plains Westchester County
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HPN
White Plains Westchester County
16 Sep - 18 Sep
$137pp
HPN
White Plains Westchester County
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-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 Sep - 18 Sep
$137pp
HPN
White Plains Westchester County
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
HPN
White Plains Westchester County
9 Oct - 10 Oct
$143pp
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
15 Sep - 20 Sep
$177pp
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 Westchester County to Chicago

Late deals on round-trip flights to Chicago from Westchester County, departing today and this week
22 May - 22 Jun
$284pp
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
22 May - 24 May
$304pp
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
27 May - 1 Jun
$305pp
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
10:02 am - 6:43 pm
JetBlue
1 Stop
9h 41m
HPN - ORD
JetBlue
5:05 am - 7:45 am
Multiple Airlines
3 Stops
27h 40m
HPN - ORD
Multiple Airlines
$141
Kiwi.com
12:35 pm - 2:17 pm
American Airlines
Nonstop
2h 42m
HPN - ORD
American Airlines

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Westchester County</span> to <span class="emphasized">Chicago</span> 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.

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.

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 0 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.

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 American Airlines for just $125, but on average you can expect to pay $169.

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

Cheapflights has at least 20 direct flights from Westchester County to Chicago under $200. A good price for a nonstop flight from Westchester County to Chicago is less than $226.

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

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

What days are nonstop flights available from Bridgeport to Chicago?

You can find nonstop flights on the following days: Tuesday.

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 $176, 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 American Airlines. Our recent data shows that you can find tickets from as low as $125 on this airline. Additional options worth looking into are United Airlines and Delta, starting at $177 and $199 round-trip. American Airlines is currently priced 56% 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 American Airlines ($49), United Airlines ($89), and Delta ($102).

Alternative routes for Westchester County 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 Westchester County to Chicago.
Flight duration
2h 28m
Average temperature for May in Chicago
71.6 °F
Avg rainfall for May in Chicago
4.3 ″

Airports servicing White Plains

White Plains Westchester County (HPN)

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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