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$139 Cheap Flights from Chicago (MDW) to Dallas (DAL)

View $139 flight on Sat, Nov 14, 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 $139 for one-way flights and $243 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Oct 27 - Sat, Oct 31
MDW
Chicago
DAL
Dallas
$243 Roundtrip, found 1 day ago
$243
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Oct 27 from Chicago to Dallas, returning Sat, Oct 31, priced at $243 found 1 day ago
Southwest Airlines
Wed, Oct 14 - Mon, Oct 19
MDW
Chicago
DAL
Dallas
$251 Roundtrip, found 2 days ago
$251
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Oct 14 from Chicago to Dallas, returning Mon, Oct 19, priced at $251 found 2 days ago
Southwest Airlines
Wed, Oct 21 - Mon, Oct 26
MDW
Chicago
DAL
Dallas
$252 Roundtrip, found 3 days ago
$252
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Chicago to Dallas, returning Mon, Oct 26, priced at $252 found 3 days ago
Delta
Wed, Dec 9 - Sat, Dec 12
MDW
Chicago
DAL
Dallas
$253 Roundtrip, found 3 days ago
$253
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Dec 9 from Chicago to Dallas, returning Sat, Dec 12, priced at $253 found 3 days ago
Southwest Airlines
Wed, Oct 28 - Tue, Nov 10
MDW
Chicago
DAL
Dallas
$255 Roundtrip, found 3 days ago
$255
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Chicago to Dallas, returning Tue, Nov 10, priced at $255 found 3 days ago
Southwest Airlines
Thu, Dec 31 - Tue, Jan 5
MDW
Chicago
DAL
Dallas
$262 Roundtrip, found 1 day ago
$262
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Dec 31 from Chicago to Dallas, returning Tue, Jan 5, priced at $262 found 1 day ago
Southwest Airlines
Fri, Oct 23 - Sat, Oct 24
MDW
Chicago
DAL
Dallas
$268 Roundtrip, found 2 days ago
$268
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Oct 23 from Chicago to Dallas, returning Sat, Oct 24, priced at $268 found 2 days ago
Southwest Airlines
Thu, Oct 22 - Mon, Oct 26
MDW
Chicago
DAL
Dallas
$269 Roundtrip, found 2 days ago
$269
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Oct 22 from Chicago to Dallas, returning Mon, Oct 26, priced at $269 found 2 days ago
Southwest Airlines
Tue, Oct 6 - Tue, Oct 13
MDW
Chicago
DAL
Dallas
$271 Roundtrip, found 2 days ago
$271
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Oct 6 from Chicago to Dallas, returning Tue, Oct 13, priced at $271 found 2 days ago
Southwest Airlines
Fri, Oct 23 - Sat, Oct 24
MDW
Chicago
DAL
Dallas
$274 Roundtrip, found 2 days ago
$274
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Oct 23 from Chicago to Dallas, returning Sat, Oct 24, priced at $274 found 2 days 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 $253
DFW
Dallas-Fort Worth Intl.
Cheapest
Average driving time to city center21 min
Flights from $253

What you need to know for your flight from Midway Intl. to Love Field

Chicago (MDW) to Dallas (DAL) at a glance

Explore a range of options for your flight from Chicago (MDW) to Dallas (DAL) on this domestic short-haul route. You can choose between full-service airlines and budget-friendly carriers to find the best itinerary that suits your travel plans, budget, and schedule. Discover the highlights of Dallas as you plan your journey, and check out the essential details for flights from Midway International Airport (MDW) to Love Field Airport (DAL).

  • Fastest flight duration: around 2h 30m non-stop
  • Route distance: roughly 800 miles (1,290 km)
  • Flights per week: around 20+ flights with multiple daily departures on average
  • Typical fares (one-way): economy tickets often range from $70–$405, depending on seasonality and how far ahead you book

Flights from Midway International Airport (MDW) to Love Field Airport (DAL)

Based on the latest traveler bookings, here are the top airlines favored for non-stop and one-stop flights from Chicago to Dallas. Many travelers opt for layovers at Kansas City International Airport (MCI, approximately 50 minutes), Hartsfield-Jackson Atlanta International Airport (ATL, around 55 minutes), and Lambert-St. Louis International Airport (STL, about 2 hours). This gives you the flexibility to mix and match options for price, total travel time, and cabin class, allowing you to discover the best itinerary for your journey.

  • Southwest Airlines: This budget-friendly airline provides both non-stop and one-stop options, with one-way ticket prices generally falling between $70 and $405. Southwest dominates this route, handling about 99% of departures, and offers a typical non-stop flight duration of 2 hours and 30 minutes.
  • Delta: As a full-service airline, Delta offers one-stop flights with one-way fares usually ranging from $100 to $240. It represents around 1% of the departures on this route, featuring an in-air time of 3 hours and 30 minutes, with an overall travel time of about 5 hours, including layover.

Best time to fly from Chicago (MDW) to Dallas (DAL)

The most popular months for travelers flying from Chicago to Dallas are March, April, and December, when peak temperatures in Dallas reach up to 65.7°F in April. If you prefer quieter travel, consider January, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 47.1°F. For better deals, May usually offers the lowest average one-way fare around $153. Flight availability peaks in December, with approximately 26 flights per week, making it easier to find convenient departure times. February has the fewest flights, with approximately 17 flights per week.

  • Cheapest time to fly: May usually offers good deals with average one-way fare around $153, roughly 13% cheaper than the yearly average.
  • More budget-friendly months to fly: October and August typically offer average one-way fares of around $162.
  • Most flight options: December has the highest number of flights from Chicago to Dallas, with approximately 26 flights per week, giving you more flexibility in scheduling your trip.
calendar iconMonthtemperature iconTemperaturecrowd level iconDemandflights iconWeekly Flightsprice iconAverage one-way Fare
January47.1°F (8.4°C)Moderately Low21$173
February49.6°F (9.8°C)Moderately Low17$187
March59.0°F (15.0°C)Moderately High19$211
April65.7°F (18.7°C)Moderately High21$178
May73.8°F (23.2°C)Average24$153
June82.9°F (28.3°C)Moderately Low22$188
July86.7°F (30.4°C)Average22$174
August87.4°F (30.8°C)Average24$162
September80.6°F (27.0°C)Average25$169
October69.1°F (20.6°C)Average22$162
November57.6°F (14.2°C)Average21$179
December50.4°F (10.2°C)Moderately High26$175

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative routes from Chicago (MDW) to Dallas (DAL)

  • Chicago to Dallas (ORD-DAL): O'Hare International Airport (ORD) is approximately 16 miles from Midway International Airport (MDW). One-way economy prices for this route generally fall between $65 and $405, influenced by the season and how far in advance you book. Travelers can find both non-stop and one-stop flight options. Major airlines operating on this route include Southwest Airlines (a low-cost carrier) and Delta.
  • Chicago to Dallas (MDW-DFW): Dallas-Fort Worth International Airport (DFW) is located about 12 miles from Love Field Airport (DAL). Economy fares for a one-way trip on this route typically range from $40 to $225, varying with the season and booking timing. This route usually provides non-stop as well as one-stop flights. Prominent airlines include Frontier Airlines (low-cost carrier) and Delta, with first-class service also available.
  • Chicago to Dallas (ORD-DFW): O'Hare International Airport (ORD) is around 16 miles from Midway International Airport (MDW), while Dallas-Fort Worth International Airport (DFW) is approximately 12 miles from Love Field Airport (DAL). One-way economy fares on this route generally vary from $45 to $345, contingent on the season and booking time. Non-stop and one-stop flight options are commonly available. Leading airlines for this route include American Airlines and Frontier Airlines (low-cost carrier), with first-class service offered as well.

How to find the best prices for flights from Chicago (MDW) to Dallas (DAL)

Getting some of the best deals on flights from Chicago to Dallas is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually available when booking at least two months in advance, though most travelers tend to book two to eight weeks beforehand. Evening departures (6 PM to 12 AM) often provide lower prices, while morning flights (5 AM to 12 PM) are the most popular. Additionally, flying on Thursday not only offers cheaper prices but is also the most favored travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Love Field Airport from Midway International Airport

Dallas welcomes travelers from Chicago with a range of transport options based on price, convenience, and proximity. Here's how to reach Dallas efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Dallas, with private rides that can be arranged in advance.
  • Car rental: Renting a car from Love Field Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Love Field Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Love Field Airport, Dallas-Love Field Seaport, a seaport, is just 0.1 miles away on foot, while Burbank Station, a metro station, is about 0.9 miles away by car. Additionally, Dallas Medical-Market Center Station, a train station, is located approximately 3.2 miles from the airport by car, offering convenient transport options.

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 $139 and cheap return flights from $243 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
$243
Distance
794 mi
Average flight time
2 hours 10 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 October. 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 $139 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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