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

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The best prices from White Plains 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
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 White Plains to Chicago

One-way from

$127

One-way flight from White Plains 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 White Plains to Chicago?

Flights from White Plains to Chicago are found to be more expensive on Saturday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

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

To save up to 10% on this flight, we recommend booking at least 20 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from White Plains to Chicago from $137 1-2 weeks out and tickets from $157 for flights departing within the next 72 hours.

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

April is one of the best times of the year to fly to Chicago from White Plains. Prices for April average $135 per person but you can even find prices for as low as $33. The most expensive prices can be found in the month of December. Opting for a April flight can save you 49% on your journey compared to booking in April

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

A simple way to save on the total cost of your ticket is to fly from White Plains to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 35% on your trip compared to booking a flight in the afternoon.

Cheap flights from White Plains 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

White Plains to Chicago 2021 flight deals

Cheap flights to Chicago from White Plains 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 White Plains

Save time with White Plains 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 White Plains to Chicago

Late deals on round-trip flights to Chicago from White Plains, 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 White Plains

The cheapest one-way flights from White Plains 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">White Plains</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From White Plains 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 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 $125, but on average you can expect to pay $169.

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 $226.

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 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 White Plains to Chicago?

For as low as $176, American Airlines can have you in Chicago from White Plains in 2h 31m. This flight may include one or multiple stops.

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

American Airlines, at $125, was found to be the cheapest airline from White Plains to Chicago.Alternate airlines to your destination round-trip include United Airlines and Delta. Users have found that American Airlines is 56% cheaper than the other options available to this destination.

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

$49 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from $89 and $102, respectively.

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
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 White Plains 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%
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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