$303 Cheap Delta flights White Plains (HPN) to Chicago (MDW)

View $303 flight on Fri, Sep 19, 2025Opens in a new window

$303 Cheap Delta flights White Plains (HPN) to Chicago (MDW)

Prices were available within the past 7 days and start at $303 for one-way flights and $297 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Sep 8 - Tue, Sep 23
HPN
White Plains
MDW
Chicago
$297 Roundtrip, found 1 day ago
$297
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Sep 8 from White Plains to Chicago, returning Tue, Sep 23, priced at $297 found 1 day ago
Delta
Mon, Sep 8 - Mon, Sep 22
HPN
White Plains
MDW
Chicago
$300 Roundtrip, found 1 day ago
$300
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Sep 8 from White Plains to Chicago, returning Mon, Sep 22, priced at $300 found 1 day ago
Delta
Wed, Sep 24 - Mon, Oct 6
HPN
White Plains
MDW
Chicago
$303 Roundtrip, found 1 day ago
$303
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 24 from White Plains to Chicago, returning Mon, Oct 6, priced at $303 found 1 day ago
Delta
Fri, Sep 5 - Tue, Sep 23
HPN
White Plains
MDW
Chicago
$312 Roundtrip, found 1 day ago
$312
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep 5 from White Plains to Chicago, returning Tue, Sep 23, priced at $312 found 1 day ago
Delta
Fri, Sep 5 - Mon, Sep 22
HPN
White Plains
MDW
Chicago
$315 Roundtrip, found 1 day ago
$315
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep 5 from White Plains to Chicago, returning Mon, Sep 22, priced at $315 found 1 day ago
Delta
Mon, Sep 8 - Sat, Sep 20
HPN
White Plains
MDW
Chicago
$317 Roundtrip, found 1 day ago
$317
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Sep 8 from White Plains to Chicago, returning Sat, Sep 20, priced at $317 found 1 day ago
Flights from White Plains (HPN) to Chicago (MDW)
Origin airport
Westchester County
Destination airport
Midway Intl.
Airlines serving
Delta
Popular airline
Delta
Distance
728 mi

Frequently asked questions

How much is a Delta Air Lines flight from Westchester County Airport (HPN) to Midway Intl. Airport (MDW)?
You'll find cheap round-trip Delta Air Lines flights from $297 from HPN to MDW by filtering your results from "Price (lowest to highest)" on Expedia. Or search for deals from $303 for a one-way trip.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly from HPN to MDW with Delta Air Lines?
Look for return or one-way flights to Chicago in January or February. You could find cheaper fares with Delta Air Lines during these off-peak times.
What is the cheapest time to book flights from Westchester County Airport (HPN) to Midway Intl. Airport (MDW) with Delta Air Lines?
Search for cheap Delta Air Lines flights from Westchester County Airport (HPN) to Midway Intl. Airport (MDW) one to three months ahead of your departure day. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. No matter the fare type and journey, the best day to book a domestic flight is generally Sunday and the most expensive day is typically Monday. Passengers who book on a Sunday can save 6% on average compared to those who book their travel on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.
Does Delta Air Lines fly nonstop from Westchester County Airport (HPN) to Midway Intl. Airport (MDW)?
Fill in your dates, hit search and check the "Nonstop" filter on Expedia to find any direct flights from HPN to MDW with Delta Air Lines or another carrier.
What is the earliest Delta Air Lines flight from HPN to MDW?
Sort your results by "Morning" and "Early Morning" to see the earliest departures from HPN to MDW. Heading off early means flight cancellations are less likely.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports does Delta Air Lines fly into in Chicago?
Midway Intl. Airport (MDW) is the primary Chicago gateway for Delta Air Lines flights from Westchester County Airport (HPN).
Why fly with Delta Air Lines from HPN to MDW?
Traveling from HPN to MDW with Delta Air Lines means enjoying plenty of perks, such as a rewarding loyalty program and an excellent in-flight experience. Plus, when you book through Expedia, One Key™ members can collect OneKeyCash™* to redeem on select future travel purchases. That's on top of the Delta SkyMiles points you can earn with Delta Air Lines.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
Can I change or cancel my Delta Air Lines flight from Westchester County Airport (HPN) to Midway Intl. Airport (MDW)?
Depending on the type of fare you purchased, a fee generally applies if you cancel or change your flight more than 24 hours after it's confirmed. To secure tickets with more flexibility, select our "Changes included" or "No cancel fee" filter when searching for flights. For additional information on canceling or changing your reservation, visit "Trips," select your flight and click on "Manage Booking."

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*Available to One Key members.