$74 Cheap Flights from Chicago (MDW) to Dallas (DAL)

View $74 flight on Tue, May 20, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Dallas (MDW-DAL)

Prices were available within the past 7 days and start at $74 for one-way flights and $162 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, May 15 - Wed, May 21
MDW
Chicago
DAL
Dallas
$162 Roundtrip, found 18 hours ago
$162
Roundtrip
found 18 hours ago
Select Southwest Airlines flight, departing Thu, May 15 from Chicago to Dallas, returning Wed, May 21, priced at $162 found 18 hours ago
Southwest Airlines
Mon, May 19 - Wed, May 21
MDW
Chicago
DAL
Dallas
$167 Roundtrip, found 8 hours ago
$167
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Mon, May 19 from Chicago to Dallas, returning Wed, May 21, priced at $167 found 8 hours ago
Delta
Sat, May 17 - Wed, May 21
MDW
Chicago
DAL
Dallas
$172 Roundtrip, found 5 hours ago
$172
Roundtrip
found 5 hours ago
Select Delta flight, departing Sat, May 17 from Chicago to Dallas, returning Wed, May 21, priced at $172 found 5 hours ago
Southwest Airlines
Wed, May 21 - Sat, May 24
MDW
Chicago
DAL
Dallas
$173 Roundtrip, found 6 hours ago
$173
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Wed, May 21 from Chicago to Dallas, returning Sat, May 24, priced at $173 found 6 hours ago
Southwest Airlines
Tue, Jul 1 - Sat, Jul 5
MDW
Chicago
DAL
Dallas
$179 Roundtrip, found 5 hours ago
$179
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Tue, Jul 1 from Chicago to Dallas, returning Sat, Jul 5, priced at $179 found 5 hours ago
Southwest Airlines
Mon, May 19 - Tue, Jun 3
MDW
Chicago
DAL
Dallas
$182 Roundtrip, found 3 hours ago
$182
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Mon, May 19 from Chicago to Dallas, returning Tue, Jun 3, priced at $182 found 3 hours ago
Southwest Airlines
Tue, May 20 - Sat, Aug 23
MDW
Chicago
DAL
Dallas
$183 Roundtrip, found 23 hours ago
$183
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Tue, May 20 from Chicago to Dallas, returning Sat, Aug 23, priced at $183 found 23 hours ago
Southwest Airlines
Wed, May 21 - Sat, May 24
MDW
Chicago
DAL
Dallas
$188 Roundtrip, found 6 hours ago
$188
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Wed, May 21 from Chicago to Dallas, returning Sat, May 24, priced at $188 found 6 hours ago
Southwest Airlines
Tue, Jul 1 - Sat, Jul 5
MDW
Chicago
DAL
Dallas
$189 Roundtrip, found 5 hours ago
$189
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Tue, Jul 1 from Chicago to Dallas, returning Sat, Jul 5, priced at $189 found 5 hours ago
Southwest Airlines
Mon, May 19 - Tue, Jun 3
MDW
Chicago
DAL
Dallas
$192 Roundtrip, found 3 hours ago
$192
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Mon, May 19 from Chicago to Dallas, returning Tue, Jun 3, priced at $192 found 3 hours ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Love Field Airport (DAL) cost?
You can pick up cheap return fares starting at $133 from Midway Intl. Airport (MDW) to Love Field Airport (DAL). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and Frontier Airlines flight leaving MDW on May 16 2025 and touching down at DAL. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from MDW to DAL?
The cheapest flights from MDW to DAL are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Love Field Airport (DAL)?
When jetting out of Midway Intl. Airport (MDW), you can take a nonstop flight to Love Field Airport (DAL) with Southwest Airlines.
What is the cheapest airline that flies from MDW to DAL?
With prices starting from $74 for a one-way journey from MDW to DAL, Southwest Airlines is currently the cheapest carrier operating this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on May 22 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Love Field Airport (DAL)?
When jetting out of Midway Intl. Airport (MDW), you’ll have your pick from an average of 4 daily direct flights to Love Field Airport (DAL).
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Love Field Airport (DAL)?
Flights between MDW and DAL are their busiest at 7 AM. If you’d like a quieter experience and potentially cheaper fares, look for a time outside the usual busy windows.
What day of the week has the most flights from MDW to DAL?
If you depart on a Friday, you’ll get the largest range of options for flights from Midway Intl. Airport (MDW) to Love Field Airport (DAL).
What is the earliest flight from Midway Intl. Airport (MDW) to Love Field Airport (DAL)?
Midway Intl. Airport (MDW)’s earliest flight to Love Field Airport (DAL) is at approximately 5:25AM UTC-6. With a total travel time of 2h 35m, you’ll touch down at around 8:00AM UTC-6.
How long does it take to fly from Midway Intl. Airport (MDW) to Love Field Airport (DAL)?
The average flight time from MDW to DAL is 2 hours and 31 minutes, covering a total distance of 800 mi.
What airline has the least delays from MDW to DAL?
Southwest Airlines has the best track record for on-time direct flights from Midway Intl. Airport (MDW) to Love Field Airport (DAL), with an on-time rating of 81%. Use the Expedia App to view your flight status before you go and get real-time updates about any trip changes.
What is the best time to fly from Midway Intl. Airport (MDW) to Love Field Airport (DAL)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Love Field Airport (DAL) route, aim to fly before 3 PM. Later departures have a 22% higher chance of cancellation.**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 Dallas from Midway Intl. Airport (MDW)?
You can arrive at Love Field Airport (DAL) or Dallas-Fort Worth Intl. Airport (DFW) when traveling to Dallas on a direct flight from Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Love Field Airport (DAL) last-minute?
Last-minute bookings from MDW to DAL are typically more expensive. To lock in the best prices, start looking for flights ahead of time. That said, if you can play around with your travel dates, it’s possible to score a cheap fare right before you leave.
Is it cheaper to book a MDW to DAL flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to DAL flight and hotel package with Expedia could lead to significant savings. What’s more, having it all in one place takes the hassle out of planning your trip. Just secure your flights and choose from our wide range of stays, then customize your trip with other add-ons like tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Love Field Airport (DAL)?
It’s usually possible to reschedule or cancel your MDW to DAL flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline’s policies in your itinerary to see what changes are allowed and whether any costs are involved. You’ll also find further details on our Customer Service portal.
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