$109 Cheap Flights from Chicago (MDW) to Dallas (DAL)

View $109 flight on Tue, May 19, 2026Opens in a new window

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

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Cheap Flights from Chicago to Dallas (MDW-DAL)

Prices were available within the past 7 days and start at $109 for one-way flights and $167 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Jun 9 - Tue, Jun 16
MDW
Chicago
DAL
Dallas
$167 Roundtrip, found 9 hours ago
$167
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Jun 9 from Chicago to Dallas, returning Tue, Jun 16, priced at $167 found 9 hours ago
Delta
Thu, Jul 2 - Wed, Jul 8
MDW
Chicago
DAL
Dallas
$202 Roundtrip, found 9 hours ago
$202
Roundtrip
found 9 hours ago
Select Delta flight, departing Thu, Jul 2 from Chicago to Dallas, returning Wed, Jul 8, priced at $202 found 9 hours ago
Southwest Airlines
Wed, May 20 - Sat, May 23
MDW
Chicago
DAL
Dallas
$202 Roundtrip, found 15 hours ago
$202
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, May 20 from Chicago to Dallas, returning Sat, May 23, priced at $202 found 15 hours ago
Southwest Airlines
Tue, Jun 9 - Tue, Jun 16
MDW
Chicago
DAL
Dallas
$206 Roundtrip, found 9 hours ago
$206
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Tue, Jun 9 from Chicago to Dallas, returning Tue, Jun 16, priced at $206 found 9 hours ago
Delta
Tue, May 12 - Wed, May 13
MDW
Chicago
DAL
Dallas
$212 Roundtrip, found 13 hours ago
$212
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, May 12 from Chicago to Dallas, returning Wed, May 13, priced at $212 found 13 hours ago
Delta
Tue, Jun 9 - Tue, Jun 16
MDW
Chicago
DAL
Dallas
$216 Roundtrip, found 9 hours ago
$216
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Jun 9 from Chicago to Dallas, returning Tue, Jun 16, priced at $216 found 9 hours ago
Southwest Airlines
Sun, Aug 16 - Tue, Aug 18
MDW
Chicago
DAL
Dallas
$216 Roundtrip, found 2 days ago
$216
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sun, Aug 16 from Chicago to Dallas, returning Tue, Aug 18, priced at $216 found 2 days ago
Southwest Airlines
Sat, May 16 - Tue, May 19
MDW
Chicago
DAL
Dallas
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sat, May 16 from Chicago to Dallas, returning Tue, May 19, priced at $217 found 1 hour ago
Southwest Airlines
Tue, Jun 9 - Tue, Jun 16
MDW
Chicago
DAL
Dallas
$221 Roundtrip, found 9 hours ago
$221
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Tue, Jun 9 from Chicago to Dallas, returning Tue, Jun 16, priced at $221 found 9 hours ago
Southwest Airlines
Thu, Jul 2 - Wed, Jul 8
MDW
Chicago
DAL
Dallas
$223 Roundtrip, found 9 hours ago
$223
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Thu, Jul 2 from Chicago to Dallas, returning Wed, Jul 8, priced at $223 found 9 hours ago

Alternative airports near Dallas

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

Select flight to Dallas-Fort Worth Intl. DFW. Cheapest option available. Average driving time to city center is 21 minutes. Flights from $138
DFW
Dallas-Fort Worth Intl.
Cheapest
Average driving time to city center21 min
Flights from $138

Frequently asked questions

How much does a flight from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field) cost?
You can find cheap one-way flights from $109 and cheap return flights from $167 Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field) with Expedia. One-way flights typically cost between $128 and $481, and return flights often range between $243 and $693. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field)?
April is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field), with average return fares around $220. This price is about 23% lower than the average for the year, as demand is typically lower in spring. Other affordable months to consider are January and May.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field)?
Enter MDW to DAL and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field)?
To find a cheap flight from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field)?
The best airline to fly with from Chicago, IL (MDW) to Dallas, TX (DAL) will differ from traveler to traveler. If you like to fly early, WN offers early morning flights. If price is the most important factor, WN typically offers the lowest fares. WN offers the most daily flights from MDW to DAL, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field)?
The best times to fly from Chicago (MDW) to Dallas (DAL) are in January and April. January has an average price of around $220, making it an affordable option. While May and December are popular months, they can be more crowded and expensive. By choosing to travel in January or April, you can enjoy lower fares and a more relaxed travel experience.*Prices based on flights available on Expedia in the last year.
How many flights per day from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field)?
You can find approximately 6 nonstop flights per day from Midway Intl. (MDW) to Love Field (DAL). For more options, look at flights that include layovers.
What is the earliest flight from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field)?
The earliest flight from Chicago Midway International Airport (MDW) to Dallas Love Field (DAL) typically departs at around 5:00 AM, operated by Southwest Airlines. This seasonal service is available in January, November, and December, allowing you to start your day early and maximize your time in Dallas. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field)?
The most popular departure times for flights from Chicago (MDW) to Dallas (DAL) are from 6am to 9am. About 26% of passengers prefer this time window. This timing is favored because it allows travelers to arrive in Dallas with plenty of time to enjoy the day. Southwest Airlines is a major carrier offering flights during this window.
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field)?
Flying nonstop from MDW to DAL takes around 2 hours 30 minutes, with the route covering approximately 794 miles. Flights with a layover typically take 5 hours 30 minutes longer than direct options. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field)?
First class seats are offered on the MDW to DAL route with Delta Air Lines.
How do I earn miles on a Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field) flight with Expedia?
It's easy to earn miles on a Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Dallas from Midway Intl. (MDW)?
From Midway Intl. (MDW), you can fly into Love Field (DAL) and Dallas-Fort Worth Intl. (DFW) in Dallas. Some flights may connect through major hubs like Lambert-St. Louis Intl. (STL), Nashville Intl. (BNA), Denver Intl. (DEN) before reaching Dallas. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field) at the last minute?
Typically, booking a last minute flight from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field) flight and hotel package?
Securing a Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field) Dallas Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field)?
If you booked your Chicago, IL (MDW-Midway Intl.) to Dallas, TX (DAL-Love Field) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Midway Intl.
Destination airport
Love Field
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$166
Distance
794 mi
Average flight time
2 hours 26 mins

Book with confidence

Chicago to Dallas Flights

The cheapest times to fly from Chicago to Dallas

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 Chicago to Dallas are during the month of June. You can find some of the cheapest flights from Chicago to Dallas with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Dallas

Sunday is one of the best days to book for cheap flights from Chicago to Dallas: 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 Chicago to Dallas

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 Chicago to Dallas in 2026. You can also book with separate airlines for your outbound and return journeys, from $109 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 Chicago to Dallas 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 Chicago to Dallas 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.

 

Chicago to Dallas Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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