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Cheap flights from White Plains to Chicago from $333

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 9/19. 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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0 bags

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Find the cheapest flights from White Plains to Chicago (HPN-MDW)

Cheap round-trip flights

Delta Logo
5:17 pm - 8:49 amHPN-MDW
16h 32m1 stop
Delta Logo
6:46 pm - 12:10 pmMDW-HPN
16h 24m1 stop
$349Delta
Find Deal
Fri, Dec 5 - Sat, Dec 13
Delta Logo
5:20 pm - 8:40 amHPN-MDW
16h 20m1 stop
Delta Logo
9:41 am - 4:34 pmMDW-HPN
5h 53m1 stop
$351Delta
Find Deal
Wed, Oct 29 - Sat, Nov 15
Delta Logo
5:17 pm - 8:49 amHPN-MDW
16h 32m1 stop
Delta Logo
9:29 am - 10:08 pmMDW-HPN
11h 39m2 stops
$354Delta
Find Deal
Fri, Dec 5 - Sat, Dec 13
Delta Logo
6:00 am - 6:25 pmHPN-MDW
13h 25m2 stops
Delta Logo
11:05 am - 6:02 pmMDW-HPN
5h 57m1 stop
$356Delta
Find Deal
Wed, Oct 29 - Sat, Nov 15
Delta Logo
6:00 am - 6:06 pmHPN-MDW
13h 06m2 stops
Delta Logo
9:29 am - 10:08 pmMDW-HPN
11h 39m2 stops
$360Delta
Find Deal
Sat, Dec 6 - Sat, Dec 13
Delta Logo
12:55 pm - 5:55 pmHPN-MDW
6h 00m1 stop
Delta Logo
6:00 am - 2:28 pmMDW-HPN
7h 28m1 stop
$369Delta
Find Deal
Sat, Nov 1 - Sat, Nov 15
Delta Logo
4:29 pm - 11:32 pmHPN-MDW
8h 03m1 stop
Delta Logo
6:46 pm - 12:10 pmMDW-HPN
16h 24m1 stop
$382Delta
Find Deal
Thu, Dec 4 - Sat, Dec 13
Delta Logo
5:10 pm - 8:50 amHPN-MDW
16h 40m1 stop
Delta Logo
5:59 pm - 11:50 amMDW-HPN
16h 51m1 stop
$385Delta
Find Deal
Mon, Jan 12 - Fri, Jan 16
Delta Logo
3:15 pm - 5:43 pmHPN-MDW
27h 28m1 stop
Delta Logo
9:35 am - 3:49 pmMDW-HPN
5h 14m1 stop
$387Delta
Find Deal
Fri, Oct 10 - Tue, Oct 14
Delta Logo
5:20 pm - 8:40 amHPN-MDW
16h 20m1 stop
Delta Logo
6:00 am - 2:28 pmMDW-HPN
7h 28m1 stop
$391Delta
Find Deal
Mon, Nov 3 - Sat, Nov 15

Delta flights from White Plains to Chicago Midway Airport

Our best Delta deals on White Plains to Chicago Midway Airport flight tickets
Delta
Dec 5
HPN5:17 pmWhite Plains Westchester County
16h 32m
1 stop
MDW8:49 amChicago Midway
Dec 13
MDW6:46 pmChicago Midway
16h 24m
1 stop
HPN12:10 pmWhite Plains Westchester County
$349
Find similar
Delta
Oct 29
HPN5:20 pmWhite Plains Westchester County
16h 20m
1 stop
MDW8:40 amChicago Midway
Nov 15
MDW9:41 amChicago Midway
5h 53m
1 stop
HPN4:34 pmWhite Plains Westchester County
$351
Find similar
Delta
Dec 5
HPN5:17 pmWhite Plains Westchester County
16h 32m
1 stop
MDW8:49 amChicago Midway
Dec 13
MDW9:29 amChicago Midway
11h 39m
2 stops
HPN10:08 pmWhite Plains Westchester County
$354
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 September 4, 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 12/5

5:17 pm-8:49 am

1 stop16h 32m

Chicago Midway

Sat 12/13

6:46 pm-12:10 pm

1 stop16h 24m

$349

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 10/29

5:20 pm-8:40 am

1 stop16h 20m

Chicago Midway

Sat 11/15

9:41 am-4:34 pm

1 stop5h 53m

$351

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 12/5

5:17 pm-8:49 am

1 stop16h 32m

Chicago Midway

Sat 12/13

9:29 am-10:08 pm

2 stops11h 39m

$354

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 10/29

6:00 am-6:25 pm

2 stops13h 25m

Chicago Midway

Sat 11/15

11:05 am-6:02 pm

1 stop5h 57m

$356

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 12/6

6:00 am-6:06 pm

2 stops13h 06m

Chicago Midway

Sat 12/13

9:29 am-10:08 pm

2 stops11h 39m

$360

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 11/1

12:55 pm-5:55 pm

1 stop6h 00m

Chicago Midway

Sat 11/15

6:00 am-2:28 pm

1 stop7h 28m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 12/4

4:29 pm-11:32 pm

1 stop8h 03m

Chicago Midway

Sat 12/13

6:46 pm-12:10 pm

1 stop16h 24m

$382

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Mon 1/12

5:10 pm-8:50 am

1 stop16h 40m

Chicago Midway

Fri 1/16

5:59 pm-11:50 am

1 stop16h 51m

$385

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 10/10

3:15 pm-5:43 pm

1 stop27h 28m

Chicago Midway

Tue 10/14

9:35 am-3:49 pm

1 stop5h 14m

$387

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Mon 11/3

5:20 pm-8:40 am

1 stop16h 20m

Chicago Midway

Sat 11/15

6:00 am-2:28 pm

1 stop7h 28m

$391

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 $271. 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, Sunday 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 $402.

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 $260 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $359. 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 4h 48m, 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
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Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
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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