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Cheap flights from White Plains to Chicago from $182

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 9/8. 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
1 adult, Economy, 0 bags

Find the cheapest flights from White Plains to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
12:38 pm - 6:31 pm
HPN
-
MDW
6h 53m
1 stop
Delta Logo
6:00 am - 12:08 pm
MDW
-
HPN
5h 08m
1 stop
$445Delta
Fri, Jul 3 - Tue, Jul 7
Delta Logo
12:36 pm - 6:25 pm
HPN
-
MDW
6h 49m
1 stop
Delta Logo
6:00 am - 2:29 pm
MDW
-
HPN
7h 29m
1 stop
$459Delta
Thu, Jul 16 - Wed, Jul 29
Delta Logo
4:29 pm - 10:36 pm
HPN
-
MDW
7h 07m
1 stop
Delta Logo
6:05 am - 2:29 pm
MDW
-
HPN
7h 24m
1 stop
$487Delta
Sat, Sep 5 - Mon, Sep 7
Delta Logo
12:38 pm - 6:31 pm
HPN
-
MDW
6h 53m
1 stop
Delta Logo
6:00 am - 12:14 pm
MDW
-
HPN
5h 14m
1 stop
$489Delta
Fri, Jul 3 - Sun, Jul 5
Delta Logo
6:40 pm - 10:45 pm
HPN
-
MDW
5h 05m
1 stop
Delta Logo
9:20 am - 4:40 pm
MDW
-
HPN
6h 20m
1 stop
$503Delta
Fri, Sep 11 - Sun, Sep 13
Delta Logo
5:12 pm - 9:13 am
HPN
-
MDW
17h 01m
1 stop
Delta Logo
6:00 am - 2:29 pm
MDW
-
HPN
7h 29m
1 stop
$511Delta
Fri, Jul 17 - Mon, Jul 27
Delta Logo
12:36 pm - 6:25 pm
HPN
-
MDW
6h 49m
1 stop
Delta Logo
6:00 am - 12:08 pm
MDW
-
HPN
5h 08m
1 stop
$517Delta
Wed, Jul 29 - Sat, Aug 1
Delta Logo
12:36 pm - 6:25 pm
HPN
-
MDW
6h 49m
1 stop
Delta Logo
6:05 am - 12:03 pm
MDW
-
HPN
4h 58m
1 stop
$527Delta
Thu, Jul 30 - Tue, Aug 4
Delta Logo
12:40 pm - 6:33 pm
HPN
-
MDW
6h 53m
1 stop
Delta Logo
6:05 am - 12:03 pm
MDW
-
HPN
4h 58m
1 stop
$531Delta
Thu, Sep 24 - Sun, Sep 27
Delta Logo
12:36 pm - 6:25 pm
HPN
-
MDW
6h 49m
1 stop
Delta Logo
6:00 am - 2:29 pm
MDW
-
HPN
7h 29m
1 stop
$533Delta
Thu, Jul 9 - Thu, Jul 16

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Delta flights from White Plains to Chicago Midway Airport

Our best Delta deals on White Plains to Chicago Midway Airport flight tickets
Delta
Jul 3
HPN12:38 pmWhite Plains Westchester County
6h 53m
1 stop
MDW6:31 pmChicago Midway
Jul 7
MDW6:00 amChicago Midway
5h 08m
1 stop
HPN12:08 pmWhite Plains Westchester County
$445
Delta
Jul 16
HPN12:36 pmWhite Plains Westchester County
6h 49m
1 stop
MDW6:25 pmChicago Midway
Jul 29
MDW6:00 amChicago Midway
7h 29m
1 stop
HPN2:29 pmWhite Plains Westchester County
$459
Delta
Jun 17
HPN12:38 pmWhite Plains Westchester County
6h 53m
1 stop
MDW6:31 pmChicago Midway
Jun 30
MDW9:17 amChicago Midway
5h 32m
1 stop
HPN3:49 pmWhite Plains Westchester County
$475

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 June 16, 2026.
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

Cheapest round-trip

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 7/3

12:38 pm-6:31 pm

1 stop6h 53m

Chicago Midway

Tue 7/7

6:00 am-12:08 pm

1 stop5h 08m

$445

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 7/16

12:36 pm-6:25 pm

1 stop6h 49m

Chicago Midway

Wed 7/29

6:00 am-2:29 pm

1 stop7h 29m

$459

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 9/5

4:29 pm-10:36 pm

1 stop7h 07m

Chicago Midway

Mon 9/7

6:05 am-2:29 pm

1 stop7h 24m

$487

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 7/3

12:38 pm-6:31 pm

1 stop6h 53m

Chicago Midway

Sun 7/5

6:00 am-12:14 pm

1 stop5h 14m

$489
Quickest round-trip

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 9/11

6:40 pm-10:45 pm

1 stop5h 05m

Chicago Midway

Sun 9/13

9:20 am-4:40 pm

1 stop6h 20m

$503

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 7/17

5:12 pm-9:13 am

1 stop17h 01m

Chicago Midway

Mon 7/27

6:00 am-2:29 pm

1 stop7h 29m

$511

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 7/29

12:36 pm-6:25 pm

1 stop6h 49m

Chicago Midway

Sat 8/1

6:00 am-12:08 pm

1 stop5h 08m

$517

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 7/30

12:36 pm-6:25 pm

1 stop6h 49m

Chicago Midway

Tue 8/4

6:05 am-12:03 pm

1 stop4h 58m

$527

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 9/24

12:40 pm-6:33 pm

1 stop6h 53m

Chicago Midway

Sun 9/27

6:05 am-12:03 pm

1 stop4h 58m

$531

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 7/9

12:36 pm-6:25 pm

1 stop6h 49m

Chicago Midway

Thu 7/16

6:00 am-2:29 pm

1 stop7h 29m

$533

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, Tuesday is the cheapest day to fly to Chicago Midway Airport from White Plains. The lowest ticket price found for a Tuesday departure recently was $276. 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 $404.

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 $230 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $372. 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

Fastest flight time

5h 05m

Direct flights

None
The fastest flight from White Plains to Chicago Midway Airport takes 5h 05m
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.
Search flight deals

Frequently asked questions about flying from White Plains to Chicago Midway Airport

  • 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 05m, 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
Portage
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Valparaiso
Schererville
Munster
Crown Point
Chesterton
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Porter
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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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