$99 Cheap Delta flights Dallas (DFW) to Chicago (MDW)

View $99 flight on Sat, Aug 9, 2025Opens in a new window

$99 Cheap Delta flights Dallas (DFW) to Chicago (MDW)

Prices were available within the past 7 days and start at $99 for one-way flights and $207 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Aug 19 - Fri, Aug 22
DAL
Dallas
MDW
Chicago
$207 Roundtrip, just found
$207
Roundtrip
just found
Select Delta flight, departing Tue, Aug 19 from Dallas to Chicago, returning Fri, Aug 22, priced at $207 just found
Flights from Dallas (DFW) to Chicago (MDW)
Origin airport
Dallas-Fort Worth Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines
Popular airline
Frontier Airlines
Distance
797 mi
Average flight time
2 hours 23 mins

Frequently asked questions

How much is a Delta Air Lines flight from Dallas-Fort Worth Intl. Airport (DFW) to Midway Intl. Airport (MDW)?
You'll discover affordable return Delta Air Lines flights from $207 from DFW to MDW by organizing your results from "Price (lowest to highest)" on Expedia. Or search for bargains from $99 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 DFW to MDW with Delta Air Lines?
Search for round-trip or one-way flights to Chicago in January or February. You could find lower fares with Delta Air Lines during these off-peak months.
What is the cheapest time to book flights from Dallas-Fort Worth Intl. Airport (DFW) to Midway Intl. Airport (MDW) with Delta Air Lines?
Start searching one to three months before your departure to find cheaper fares on Delta Air Lines flights from Dallas-Fort Worth Intl. Airport (DFW) to Midway Intl. Airport (MDW). You can save 25% by booking your domestic flight 34 to 86 days in advance versus last-minute reservations made 6 to 12 days out. You could also reduce costs by buying your fare on a Sunday, as it's 6% cheaper on average than a Monday, the most expensive day to book.* Get the timing right, and you can enjoy significant savings on domestic journeys.*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 Dallas-Fort Worth Intl. Airport (DFW) to Midway Intl. Airport (MDW)?
Use our "Nonstop" filter when browsing for direct Delta Air Lines flights from DFW to MDW. You can also compare other airlines offering the same direct trip.
What is the earliest Delta Air Lines flight from DFW to MDW?
Sort your results by "Morning" and "Early Morning" to browse the earliest departures from DFW to MDW. Jetting off early means you're less likely to experience cancellations.**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?
Delta Air Lines flights from Dallas-Fort Worth Intl. Airport (DFW) to Chicago land at Midway Intl. Airport (MDW). This is the main entry point to this destination.
Why fly with Delta Air Lines from DFW to MDW?
Traveling from DFW to MDW with Delta Air Lines comes with a range of perks, such as a rewarding loyalty program and an excellent in-flight experience. Plus, when booking through Expedia, One Key™ members can earn OneKeyCash™* to spend on select future travel purchases. That's in addition to 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 Dallas-Fort Worth Intl. Airport (DFW) to Midway Intl. Airport (MDW)?
Depending on the ticket type you purchased, a fee typically applies if you cancel or change your booking more than 24 hours after it has been confirmed. To secure tickets with more flexibility, select our "Changes included" and "No cancel fee" boxes when looking for flights. For additional information on modifying or canceling your reservation, visit "Trips," select your flight and tick "Manage Booking."

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*Available to One Key members.