$59 Cheap Flights from Dallas (DAL) to Chicago (MDW)

View $59 flight on Fri, Feb 13, 2026Opens in a new window

Popular airlines from Love Field Airport (DAL) to Chicago Midway Airport (MDW)

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Today's featured flight deals from Love Field Airport (DAL) to Chicago Midway Airport (MDW)

Nonstop
Carry-on included
Lower price than typical

Cheap Flights from Dallas to Chicago (DAL-MDW)

Prices were available within the past 7 days and start at $59 for one-way flights and $117 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Fri, Jan 23 - Sun, Jan 25
DAL
Dallas
MDW
Chicago
$117 Roundtrip, found 3 hours ago
$117
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Fri, Jan 23 from Dallas to Chicago, returning Sun, Jan 25, priced at $117 found 3 hours ago
Southwest Airlines
Wed, Dec 31 - Tue, Jan 6
DAL
Dallas
MDW
Chicago
$136 Roundtrip, found 3 days ago
$136
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Dec 31 from Dallas to Chicago, returning Tue, Jan 6, priced at $136 found 3 days ago
Southwest Airlines
Sat, Dec 13 - Sun, Jan 11
DAL
Dallas
MDW
Chicago
$137 Roundtrip, found 3 hours ago
$137
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Sat, Dec 13 from Dallas to Chicago, returning Sun, Jan 11, priced at $137 found 3 hours ago
Southwest Airlines
Wed, Dec 24 - Thu, Jan 1
DAL
Dallas
MDW
Chicago
$140 Roundtrip, found 6 days ago
$140
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Dec 24 from Dallas to Chicago, returning Thu, Jan 1, priced at $140 found 6 days ago
Southwest Airlines
Fri, Jan 16 - Sat, Jan 17
DAL
Dallas
MDW
Chicago
$142 Roundtrip, found 2 days ago
$142
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Jan 16 from Dallas to Chicago, returning Sat, Jan 17, priced at $142 found 2 days ago
Southwest Airlines
Thu, Jan 15 - Tue, Jan 20
DAL
Dallas
MDW
Chicago
$143 Roundtrip, found 5 hours ago
$143
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Thu, Jan 15 from Dallas to Chicago, returning Tue, Jan 20, priced at $143 found 5 hours ago
Southwest Airlines
Tue, Jan 20 - Sat, Jan 24
DAL
Dallas
MDW
Chicago
$146 Roundtrip, found 1 day ago
$146
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Jan 20 from Dallas to Chicago, returning Sat, Jan 24, priced at $146 found 1 day ago
Southwest Airlines
Fri, Jan 16 - Mon, Jan 19
DAL
Dallas
MDW
Chicago
$147 Roundtrip, found 5 hours ago
$147
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Fri, Jan 16 from Dallas to Chicago, returning Mon, Jan 19, priced at $147 found 5 hours ago
Southwest Airlines
Wed, Jan 14 - Wed, Mar 4
DAL
Dallas
MDW
Chicago
$148 Roundtrip, found 3 days ago
$148
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Jan 14 from Dallas to Chicago, returning Wed, Mar 4, priced at $148 found 3 days ago
Southwest Airlines
Sat, Jan 17 - Sun, Jan 18
DAL
Dallas
MDW
Chicago
$151 Roundtrip, found 4 days ago
$151
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Dallas to Chicago, returning Sun, Jan 18, priced at $151 found 4 days ago

Find the cheapest month to fly from Dallas (DAL) to Chicago (MDW)

August is typically the cheapest month to fly

From $106 - $417 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $273
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $273

Frequently asked questions

How much does a flight from Love Field Airport (DAL) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $59 or cheap return flight from $117 from Love Field Airport (DAL) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Love Field Airport (DAL) to Midway Intl. Airport (MDW)?
January is the cheapest month to fly from DAL to MDW. Traveling outside of peak seasons is often the key to better flight prices.
Which airlines fly direct from Love Field Airport (DAL) to Midway Intl. Airport (MDW)?
When flying out of Love Field Airport (DAL), you can hop on a nonstop flight to Midway Intl. Airport (MDW) with Southwest Airlines.
What is the cheapest airline that flies from Love Field Airport (DAL) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll take you from DAL to MDW. Then, sort your results by "Price (lowest to highest)" to snap up the best deal available.
How many flights per day from Love Field Airport (DAL) to Midway Intl. Airport (MDW)?
Every day, an average of 4 nonstop flights take off from Love Field Airport (DAL) to Midway Intl. Airport (MDW). Select the departure time that best suits your travel plans.
What are the most popular departure times for flights from Love Field Airport (DAL) to Midway Intl. Airport (MDW)?
Flights between DAL and MDW are busiest at 7 PM. If you'd like a more relaxed trip and possibly cheaper fares, look for a departure outside the usual busy windows.
What day of the week has the most flights from DAL to MDW?
Travel on a Thursday if you're after the biggest selection of flights from Love Field Airport (DAL) to Midway Intl. Airport (MDW).
What is the earliest flight from Love Field Airport (DAL) to Midway Intl. Airport (MDW)?
Love Field Airport (DAL)'s first flight to Midway Intl. Airport (MDW) takes off at approximately 6:55AM UTC-6. With a total journey time of 2h 10m, you'll arrive at around 9:05AM UTC-6.
How long does it take to fly from Love Field Airport (DAL) to Midway Intl. Airport (MDW)?
Typically, it takes 2 hours and 9 minutes to cover the 800 mi from DAL to MDW.
What is the best time to fly from Love Field Airport (DAL) to Midway Intl. Airport (MDW)?
Opt for a flight from Love Field Airport (DAL) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of delays and cancellations. Departures later than this are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Love Field Airport (DAL)?
If you're leaving on a direct flight from Love Field Airport (DAL) to Chicago, you can arrive at either O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Love Field Airport (DAL) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from DAL to MDW just before your trip is typically more expensive. But if you're flexible with your departure times and dates, you could snag a cheap last-minute fare.
Is it cheaper to book a DAL to MDW flight and hotel package?
Booking a DAL to MDW flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Select from our impressive range of stays and then add flights, car rentals and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Love Field Airport (DAL) to Midway Intl. Airport (MDW)?
If you booked your DAL to MDW flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more details.

Travel information

Origin airport
Love Field
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$117
Distance
794 mi
Average flight time
2 hours 11 mins

Book with confidence

Dallas to Chicago Flights

The cheapest times to fly from Dallas to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Dallas to Chicago are during the month of January. You can find some of the cheapest flights from Dallas to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Dallas to Chicago

Sunday is one of the best days to book for cheap flights from Dallas to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Dallas to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Dallas to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $59 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Dallas to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Dallas to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Dallas to Chicago Flights

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*Available to One Key members.