Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from White Plains to Chicago from $106

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from White Plains to Chicago departing on 12/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from White Plains to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:00 am - 7:44 amHPN-ORD
2h 44mnonstop
American Airlines Logo
9:45 am - 4:46 pmORD-HPN
6h 01m1 stop
$359American Airlines
Find Deal
Tue, Dec 2 - Tue, Dec 9
Delta Logo
12:55 pm - 6:00 pmHPN-MDW
6h 05m1 stop
Delta Logo
6:00 am - 2:28 pmMDW-HPN
7h 28m1 stop
$369Delta
Find Deal
Tue, Dec 2 - Tue, Dec 9
Delta Logo
3:15 pm - 7:56 pmHPN-ORD
5h 41m1 stop
Delta Logo
9:30 am - 4:40 pmORD-HPN
6h 10m1 stop
$369Delta
Find Deal
Tue, Apr 7 - Sat, Apr 11
American Airlines Logo
4:30 pm - 6:23 pmHPN-ORD
2h 53mnonstop
American Airlines Logo
12:49 pm - 3:59 pmORD-HPN
2h 10mnonstop
$380American Airlines
Find Deal
Sat, Dec 13 - Mon, Dec 15
Multiple Airlines Logo
12:10 pm - 11:28 pmHPN-ORD
12h 18m1 stop
Multiple Airlines Logo
5:15 am - 11:29 amORD-HPN
29h 14m2 stops
$382Multiple Airlines
Find Deal
Fri, Nov 14 - Mon, Nov 17
American Airlines Logo
7:59 am - 2:17 pmHPN-ORD
7h 18m1 stop
American Airlines Logo
12:50 pm - 3:59 pmORD-HPN
2h 09mnonstop
$390American Airlines
Find Deal
Sat, Dec 13 - Mon, Dec 22
American Airlines Logo
5:56 pm - 7:43 pmHPN-ORD
2h 47mnonstop
American Airlines Logo
8:10 am - 11:29 amORD-HPN
2h 19mnonstop
$399American Airlines
Find Deal
Sat, Dec 20 - Sat, Dec 27
Delta Logo
12:55 pm - 6:06 pmHPN-MDW
6h 11m1 stop
Delta Logo
6:00 am - 12:00 pmMDW-HPN
5h 00m1 stop
$400Delta
Find Deal
Sat, Dec 13 - Mon, Dec 15
Delta Logo
3:08 pm - 9:40 pmHPN-ORD
7h 32m1 stop
Delta Logo
9:41 am - 3:49 pmORD-HPN
5h 08m1 stop
$400Delta
Find Deal
Sat, Dec 13 - Mon, Dec 22
Delta Logo
12:55 pm - 4:36 pmHPN-ORD
4h 41m1 stop
Delta Logo
6:45 am - 11:59 amORD-HPN
4h 14m1 stop
$404Delta
Find Deal
Thu, Nov 27 - Tue, Dec 2

American Airlines flights from White Plains to Chicago

Our best American Airlines deals on White Plains to Chicago flight tickets
American Airlines
Dec 2
HPN6:00 amWhite Plains Westchester County
2h 44m
ORD7:44 amChicago O'Hare Intl
Dec 9
ORD9:45 amChicago O'Hare Intl
6h 01m
1 stop
HPN4:46 pmWhite Plains Westchester County
$359
Find similar
American Airlines
Dec 13
HPN4:30 pmWhite Plains Westchester County
2h 53m
ORD6:23 pmChicago O'Hare Intl
Dec 15
ORD12:49 pmChicago O'Hare Intl
2h 10m
HPN3:59 pmWhite Plains Westchester County
$380
Find similar
American Airlines
Dec 13
HPN7:59 amWhite Plains Westchester County
7h 18m
1 stop
ORD2:17 pmChicago O'Hare Intl
Dec 22
ORD12:50 pmChicago O'Hare Intl
2h 09m
HPN3:59 pmWhite Plains Westchester County
$390
Find similar

Delta flights from White Plains to Chicago

Our best Delta deals on White Plains to Chicago flight tickets
Delta
Apr 7
HPN3:15 pmWhite Plains Westchester County
5h 41m
1 stop
ORD7:56 pmChicago O'Hare Intl
Apr 11
ORD9:30 amChicago O'Hare Intl
6h 10m
1 stop
HPN4:40 pmWhite Plains Westchester County
$369
Find similar
Delta
Dec 13
HPN3:08 pmWhite Plains Westchester County
7h 32m
1 stop
ORD9:40 pmChicago O'Hare Intl
Dec 22
ORD9:41 amChicago O'Hare Intl
5h 08m
1 stop
HPN3:49 pmWhite Plains Westchester County
$400
Find similar
Delta
Nov 27
HPN12:55 pmWhite Plains Westchester County
4h 41m
1 stop
ORD4:36 pmChicago O'Hare Intl
Dec 2
ORD6:45 amChicago O'Hare Intl
4h 14m
1 stop
HPN11:59 amWhite Plains Westchester County
$404
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from White Plains to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 3, 2025.
Use the filters below to find and compare flights from White Plains to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 12/2

6:00 am-7:44 am

Nonstop2h 44m

Chicago O'Hare Intl

Tue 12/9

9:45 am-4:46 pm

1 stop6h 01m

$359

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 12/2

12:55 pm-6:00 pm

1 stop6h 05m

Chicago Midway

Tue 12/9

6:00 am-2:28 pm

1 stop7h 28m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 4/7

3:15 pm-7:56 pm

1 stop5h 41m

Chicago O'Hare Intl

Sat 4/11

9:30 am-4:40 pm

1 stop6h 10m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 12/13

4:30 pm-6:23 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 12/15

12:49 pm-3:59 pm

Nonstop2h 10m

$380

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 11/14

12:10 pm-11:28 pm

1 stop12h 18m

Chicago O'Hare Intl

Mon 11/17

5:15 am-11:29 am

2 stops29h 14m

$382

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 12/13

7:59 am-2:17 pm

1 stop7h 18m

Chicago O'Hare Intl

Mon 12/22

12:50 pm-3:59 pm

Nonstop2h 09m

$390

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 12/20

5:56 pm-7:43 pm

Nonstop2h 47m

Chicago O'Hare Intl

Sat 12/27

8:10 am-11:29 am

Nonstop2h 19m

$399

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 12/13

12:55 pm-6:06 pm

1 stop6h 11m

Chicago Midway

Mon 12/15

6:00 am-12:00 pm

1 stop5h 00m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 12/13

3:08 pm-9:40 pm

1 stop7h 32m

Chicago O'Hare Intl

Mon 12/22

9:41 am-3:49 pm

1 stop5h 08m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 11/27

12:55 pm-4:36 pm

1 stop4h 41m

Chicago O'Hare Intl

Tue 12/2

6:45 am-11:59 am

1 stop4h 14m

$404

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from White Plains to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from White Plains, with most prices found around $450. If you’re not able to fly to Chicago in September, then March is your next best option. Flight prices from White Plains to Chicago during March average around $456.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $293. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from White Plains to Chicago for around $386.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from White Plains to Chicago during this time can be as low as $271. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $367.

What is the cheapest White Plains Westchester County to Chicago flight route?

Fly from White Plains Westchester County to Chicago O'Hare Intl for the best White Plains Westchester County - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from White Plains when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $469 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from White Plains for as low as $379 on momondo.

What cabin class options are available on White Plains Westchester County to Chicago flights?

There are 3 cabin classes available to choose from on White Plains Westchester County to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on White Plains to Chicago flights?

You could potentially save up to 7% on your flight if you consider stops on a White Plains to Chicago flight.

How have White Plains to Chicago flight prices changed over time?

As of November 2025, prices for White Plains to Chicago flights are approximately 30% more expensive when compared to flights at the same time last year.

When to book flights from White Plains to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from White Plains to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap White Plains to Chicago (HPN to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from White Plains to Chicago

Best Price Found

$205

Fastest flight time

2h 34m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from White Plains in the past 72 hours is $205. The best round-trip flight deal from White Plains to Chicago found on momondo in the last 72 hours is $428.
The fastest flight from White Plains to Chicago takes 2h 34m
Direct flights go from White Plains to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • How far is White Plains Westchester County to Chicago by plane?

    Chicago is 719.0 mi away from White Plains Westchester County. A reasonable flight in good conditions will take 2h 35m.

  • When did momondo last update prices for flights from White Plains Westchester County Airport to Chicago?

    Prices for flights from White Plains Westchester County Airport to Chicago are updated daily.

  • How many operators does momondo search for flights from White Plains Westchester County Airport to Chicago?

  • How old do you have to be to fly from White Plains Westchester County Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from White Plains Westchester County Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from White Plains to Chicago?

  • What is the most popular airline from White Plains to Chicago?

Best airlines flying from White Plains to Chicago

Compare and see reviews for airlines that fly from White Plains to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $349Free CancellationRating
7.2
11,037 reviews
Search American Airlines flights

  • American Airlines Flights From White Plains to Chicago

    Across 33 American Airlines flights from White Plains to Chicago this week, the average price was $480, with the best American Airlines deals starting from $349 round-trip. 11,037 users have rated American Airlines on momondo, with an average score of 7.2/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from White Plains to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from White Plains to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from White Plains to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for White Plains to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from White Plains to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from White Plains to Chicago.

I’m not ready to book a flight from White Plains to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from White Plains are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 12/3
Wed 12/10
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport