$128 Cheap Flights from Dallas (DAL) to Chicago (MDW)

View $128 flight on Wed, Aug 26, 2026Opens in a new window

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

Cheap Flights from Dallas to Chicago (DAL-MDW)

Prices were available within the past 7 days and start at $128 for one-way flights and $202 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Jun 9 - Sat, Jun 13
DAL
Dallas
MDW
Chicago
$202 Roundtrip, found 6 days ago
$202
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Jun 9 from Dallas to Chicago, returning Sat, Jun 13, priced at $202 found 6 days ago
Southwest Airlines
Thu, Sep 10 - Mon, Sep 14
DAL
Dallas
MDW
Chicago
$209 Roundtrip, found 6 days ago
$209
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Sep 10 from Dallas to Chicago, returning Mon, Sep 14, priced at $209 found 6 days ago
Southwest Airlines
Tue, Aug 25 - Fri, Aug 28
DAL
Dallas
MDW
Chicago
$255 Roundtrip, found 16 hours ago
$255
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Tue, Aug 25 from Dallas to Chicago, returning Fri, Aug 28, priced at $255 found 16 hours ago
Southwest Airlines
Fri, Jul 3 - Tue, Jul 7
DAL
Dallas
MDW
Chicago
$263 Roundtrip, found 19 hours ago
$263
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Fri, Jul 3 from Dallas to Chicago, returning Tue, Jul 7, priced at $263 found 19 hours ago
Southwest Airlines
Wed, Jul 15 - Sat, Jul 18
DAL
Dallas
MDW
Chicago
$265 Roundtrip, found 16 hours ago
$265
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Wed, Jul 15 from Dallas to Chicago, returning Sat, Jul 18, priced at $265 found 16 hours ago
Southwest Airlines
Wed, May 27 - Wed, Jun 3
DAL
Dallas
MDW
Chicago
$268 Roundtrip, found 1 day ago
$268
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, May 27 from Dallas to Chicago, returning Wed, Jun 3, priced at $268 found 1 day ago
Southwest Airlines
Wed, May 20 - Sun, May 24
DAL
Dallas
MDW
Chicago
$269 Roundtrip, found 9 hours ago
$269
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Wed, May 20 from Dallas to Chicago, returning Sun, May 24, priced at $269 found 9 hours ago
Southwest Airlines
Wed, Jul 15 - Wed, Jul 22
DAL
Dallas
MDW
Chicago
$271 Roundtrip, found 18 hours ago
$271
Roundtrip
found 18 hours ago
Select Southwest Airlines flight, departing Wed, Jul 15 from Dallas to Chicago, returning Wed, Jul 22, priced at $271 found 18 hours ago
Southwest Airlines
Wed, Aug 26 - Sun, Aug 30
DAL
Dallas
MDW
Chicago
$273 Roundtrip, found 1 day ago
$273
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Aug 26 from Dallas to Chicago, returning Sun, Aug 30, priced at $273 found 1 day ago
Delta
Mon, Jun 8 - Tue, Jun 23
DAL
Dallas
MDW
Chicago
$280 Roundtrip, found 1 day ago
$280
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Jun 8 from Dallas to Chicago, returning Tue, Jun 23, priced at $280 found 1 day ago

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. Average driving time to city center is 23 minutes. Flights from $367
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $367

Frequently asked questions

How much does a flight from Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights and cheap return flights from $202 Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights generally range between $89 and $468, and roundtrip flights usually range from $224 to $688. 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 Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.) 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 Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from DAL to MDW is June when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.)?
Enter DAL to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.)?
Southwest Airlines is one of the cheapest airlines offering nonstop flights from Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.), with round-trip tickets starting from around $433. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.), 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 Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.)?
The best airline to fly with from Dallas, TX (DAL) to Chicago, IL (MDW) 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 also offers the most daily flights from DAL to MDW, 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 Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.)?
You can find approximately 6 nonstop flights per day from Love Field (DAL) to Midway Intl. (MDW). For more options, look at flights that include layovers.
What is the earliest flight from Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Love Field (DAL) to Midway International (MDW) typically departs at around 5:45 AM, operated by Delta. This seasonal service is active in June, July, and August, making it a convenient option for summer travel. An early flight allows you to arrive in Chicago with plenty of time to enjoy your day. 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 Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Dallas (DAL) to Chicago (MDW) are in the early morning, from 6am to 9am. About 27% of passengers prefer this time window. Many major carriers, including Southwest Airlines, offer flights during this window. This timing is favored as it allows you to arrive in Chicago early and make the most of your day.
How long does it take to fly from Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.)?
Direct flights from DAL to MDW usually take about 2 hours 20 minutes, traveling roughly 794 miles. If you opt for a connecting flight, expect to add around 3 hours 40 minutes to your journey. 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 Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the DAL to MDW route with Delta Air Lines.
How do I earn miles on a Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.) 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 Chicago from Love Field (DAL)?
From Love Field (DAL), you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD) in Chicago. Some flights may connect through major hubs like William P. Hobby (HOU), Austin-Bergstrom Intl. (AUS), Baltimore Washington Intl. Thurgood Marshall (BWI) before reaching Chicago. 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 Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.) 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 Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.) Chicago 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 Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Dallas, TX (DAL-Love Field) to Chicago, IL (MDW-Midway Intl.) 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
Love Field
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$180
Distance
794 mi
Average flight time
2 hours 13 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 June. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $128 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

*Flight schedules are subject to change.

*Available to One Key members.

 

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