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Cheap flights from White Plains to Chicago from $141

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 12/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from White Plains to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
12:36 pm - 5:37 pmHPN-MDW
6h 01m1 stop
Delta Logo
11:21 am - 6:00 pmMDW-HPN
5h 39m1 stop
$400Delta
Find Deal
Fri, Jan 9 - Tue, Jan 13
Delta Logo
12:55 pm - 6:00 pmHPN-MDW
6h 05m1 stop
Delta Logo
9:29 am - 3:49 pmMDW-HPN
5h 20m1 stop
$431Delta
Find Deal
Fri, Dec 19 - Sun, Dec 21
Delta Logo
4:19 pm - 9:45 pmHPN-MDW
6h 26m1 stop
Delta Logo
9:30 am - 12:14 pmMDW-HPN
25h 44m2 stops
$435Delta
Find Deal
Sat, May 2 - Tue, May 5
Delta Logo
6:50 pm - 11:47 pmHPN-MDW
5h 57m1 stop
Delta Logo
9:34 am - 3:49 pmMDW-HPN
5h 15m1 stop
$469Delta
Find Deal
Sat, Dec 6 - Tue, Dec 9
Delta Logo
6:50 pm - 11:47 pmHPN-MDW
5h 57m1 stop
Delta Logo
6:00 am - 12:00 pmMDW-HPN
5h 00m1 stop
$487Delta
Find Deal
Fri, Dec 12 - Sun, Dec 14
Delta Logo
12:55 pm - 6:06 pmHPN-MDW
6h 11m1 stop
Delta Logo
6:00 am - 12:00 pmMDW-HPN
5h 00m1 stop
$506Delta
Find Deal
Sat, Dec 13 - Sun, Dec 14
Delta Logo
12:55 pm - 6:00 pmHPN-MDW
6h 05m1 stop
Delta Logo
9:29 am - 3:49 pmMDW-HPN
5h 20m1 stop
$530Delta
Find Deal
Fri, Dec 19 - Tue, Dec 23
Delta Logo
6:50 pm - 11:47 pmHPN-MDW
5h 57m1 stop
Delta Logo
9:34 am - 3:49 pmMDW-HPN
5h 15m1 stop
$543Delta
Find Deal
Fri, Dec 5 - Sun, Dec 7
Delta Logo
4:29 pm - 11:47 pmHPN-MDW
8h 18m1 stop
Delta Logo
9:29 am - 3:49 pmMDW-HPN
5h 20m1 stop
$559Delta
Find Deal
Tue, Dec 16 - Tue, Dec 23
Delta Logo
6:00 am - 6:31 pmHPN-MDW
13h 31m2 stops
Delta Logo
9:30 am - 9:41 pmMDW-HPN
11h 11m2 stops
$568Delta
Find Deal
Sat, May 2 - Tue, May 5

Delta flights from White Plains to Chicago Midway Airport

Our best Delta deals on White Plains to Chicago Midway Airport flight tickets
Delta
Jan 9
HPN12:36 pmWhite Plains Westchester County
6h 01m
1 stop
MDW5:37 pmChicago Midway
Jan 13
MDW11:21 amChicago Midway
5h 39m
1 stop
HPN6:00 pmWhite Plains Westchester County
$400
Find similar
Delta
Dec 19
HPN12:55 pmWhite Plains Westchester County
6h 05m
1 stop
MDW6:00 pmChicago Midway
Dec 21
MDW9:29 amChicago Midway
5h 20m
1 stop
HPN3:49 pmWhite Plains Westchester County
$431
Find similar
Delta
May 2
HPN4:19 pmWhite Plains Westchester County
6h 26m
1 stop
MDW9:45 pmChicago Midway
May 5
MDW9:30 amChicago Midway
25h 44m
2 stops
HPN12:14 pmWhite Plains Westchester County
$435
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from White Plains to Chicago Midway Airport 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 17, 2025.
Use the filters below to find and compare flights from White Plains to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 1/9

12:36 pm-5:37 pm

1 stop6h 01m

Chicago Midway

Tue 1/13

11:21 am-6:00 pm

1 stop5h 39m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 12/19

12:55 pm-6:00 pm

1 stop6h 05m

Chicago Midway

Sun 12/21

9:29 am-3:49 pm

1 stop5h 20m

$431

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 5/2

4:19 pm-9:45 pm

1 stop6h 26m

Chicago Midway

Tue 5/5

9:30 am-12:14 pm

2 stops25h 44m

$435

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 12/6

6:50 pm-11:47 pm

1 stop5h 57m

Chicago Midway

Tue 12/9

9:34 am-3:49 pm

1 stop5h 15m

$469

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 12/12

6:50 pm-11:47 pm

1 stop5h 57m

Chicago Midway

Sun 12/14

6:00 am-12:00 pm

1 stop5h 00m

$487

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 12/13

12:55 pm-6:06 pm

1 stop6h 11m

Chicago Midway

Sun 12/14

6:00 am-12:00 pm

1 stop5h 00m

$506

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 12/19

12:55 pm-6:00 pm

1 stop6h 05m

Chicago Midway

Tue 12/23

9:29 am-3:49 pm

1 stop5h 20m

$530

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 12/5

6:50 pm-11:47 pm

1 stop5h 57m

Chicago Midway

Sun 12/7

9:34 am-3:49 pm

1 stop5h 15m

$543

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 12/16

4:29 pm-11:47 pm

1 stop8h 18m

Chicago Midway

Tue 12/23

9:29 am-3:49 pm

1 stop5h 20m

$559

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 5/2

6:00 am-6:31 pm

2 stops13h 31m

Chicago Midway

Tue 5/5

9:30 am-9:41 pm

2 stops11h 11m

$568

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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 day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from White Plains. The lowest ticket price found for a Wednesday departure recently was $275. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from White Plains because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $422.

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

Flying to Chicago Midway Airport from White Plains in the evening is the least expensive time of day to depart. momondo users have found prices as low as $243 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $360. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from White Plains to Chicago Midway Airport

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

Cheap White Plains to Chicago Midway Airport (HPN to MDW) flight deals and tips

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

Direct flights

None
There are no direct flights from White Plains to Chicago Midway Airport. There are no popular flight routes from White Plains to Chicago Midway Airport.
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  • How far is White Plains Westchester County to Chicago Midway by plane?

    There are 725.1 mi between White Plains Westchester County and Chicago Midway. Flights usually cover this in 5h 31m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from White Plains Westchester County Airport to Chicago Midway Airport are refreshed on a daily basis.

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from White Plains Westchester County Airport to Chicago Midway Airport.

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

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from White Plains to Chicago for you.

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

Flights from White Plains to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for White Plains to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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.

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