$117 Cheap Flights from Dallas (DAL) to Chicago (MDW)
Popular airlines from Love Field Airport (DAL) to Chicago Midway Airport (MDW)
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Cheap Flights from Dallas to Chicago (DAL-MDW)
Alternative airports near Chicago
Prices were available within the past 7 days. Prices and availability are subject to change.
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Dallas (DAL) to Chicago (MDW) at a glance
Travel on a variety of airlines offering routes from Dallas (DAL) to Chicago (MDW) on this domestic short-haul journey. Discover cheap flights from Dallas and compare options from both full-service and low-cost carriers to find an itinerary that aligns with your budget and schedule. As you plan your trip to explore Chicago's iconic sights and vibrant neighborhoods, check out the essential details for flights from Love Field Airport (DAL) to Midway International Airport (MDW).
- Fastest flight duration: around 2h 15m 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 Love Field Airport (DAL) to Midway International Airport (MDW)
Based on recent traveler bookings, here are the top airlines favored for flights from Dallas to Chicago, highlighting options for both non-stop and one-stop journeys. Common layover spots include Lambert-St. Louis International Airport (STL) with a 55-minute stop, Kansas City International Airport (MCI) offering a 1 hour and 15-minute layover, and Hartsfield-Jackson Atlanta International Airport (ATL), also featuring a 1 hour and 15-minute stop. These choices provide the flexibility to balance price, total travel time, and cabin class to create your ideal itinerary.
- Southwest Airlines: This budget-friendly airline provides both non-stop and one-stop options, with one-way prices generally falling between $70 and $405. It dominates this route with nearly 99% of departures. Expect a typical non-stop flight duration of around 2 hours and 15 minutes.
- Delta: Offering one-stop services, Delta is a full-service airline with one-way fares typically ranging from $90 to $395. This carrier constitutes about 1% of departures on this route, featuring an in-flight time of 3 hours and 30 minutes, totaling approximately 4 hours and 45 minutes, including layover time.
Best time to fly from Dallas (DAL) to Chicago (MDW)
The most popular months for travelers flying from Dallas to Chicago are March, April, and December, when peak temperatures in Chicago reach up to 46°F in April. If you prefer quieter travel, consider June, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 67.3°F. For better deals, September usually offers the lowest average one-way fare around $151. Flight availability peaks in August, with approximately 29 flights per week, making it easier to find convenient departure times. February has the fewest flights, with approximately 18 flights per week.
- Cheapest time to fly: September usually offers good deals with average one-way fare around $151, roughly 15% cheaper than the yearly average.
- More budget-friendly months to fly: October and May typically offer average one-way fares of around $157.
- Most flight options: August has the highest number of flights from Dallas to Chicago, with approximately 29 flights per week, giving you more flexibility in scheduling your trip.
| Month | Temperature | Demand | Weekly Flights | Average one-way Fare |
| January | 25.7°F (-3.5°C) | Average | 20 | $181 |
| February | 27.0°F (-2.8°C) | Moderately Low | 18 | $202 |
| March | 37.0°F (2.8°C) | Moderately High | 22 | $209 |
| April | 46.0°F (7.8°C) | Moderately High | 23 | $181 |
| May | 57.0°F (13.9°C) | Average | 28 | $157 |
| June | 67.3°F (19.6°C) | Moderately Low | 21 | $180 |
| July | 73.4°F (23.0°C) | Moderately Low | 21 | $195 |
| August | 73.0°F (22.8°C) | Average | 29 | $169 |
| September | 67.1°F (19.5°C) | Average | 28 | $151 |
| October | 54.9°F (12.7°C) | Average | 24 | $157 |
| November | 42.3°F (5.7°C) | Average | 27 | $181 |
| December | 33.1°F (0.6°C) | Moderately High | 26 | $172 |
*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 Dallas (DAL) to Chicago (MDW)
- Dallas to Chicago (DAL-ORD): O'Hare International Airport (ORD) is located approximately 16 miles from Midway International Airport (MDW). One-way economy ticket prices for this journey generally fall between $65 and $405, influenced by the time of year and when you book. Travelers can choose from both non-stop and one-stop flight options. Leading airlines for this route include the budget-friendly Southwest Airlines and Delta.
- Dallas to Chicago (DFW-MDW): Dallas-Fort Worth International Airport (DFW) is about 12 miles from Love Field Airport (DAL). On this route, one-way economy fares usually range from $35 to $225, varying based on seasonal demand and booking timing. Passengers can select from non-stop and one-stop flights. Popular airlines that service this route encompass Frontier Airlines, known for its low-cost fares, as well as Delta.
- Dallas to Chicago (DFW-ORD): Dallas-Fort Worth International Airport (DFW) lies roughly 12 miles from Love Field Airport (DAL), while O'Hare International Airport (ORD) is around 16 miles from Midway International Airport (MDW). Economy fares for one-way flights on this route typically range from $50 to $355, influenced by the season and when you book your ticket. Both non-stop and one-stop options are available. Major airlines operating this route include American Airlines and the budget-friendly Frontier Airlines. Additionally, first-class service is offered on this route.
How to find the best prices for flights from Dallas (DAL) to Chicago (MDW)
Getting some of the best deals on flights from Dallas to Chicago is all about timing and flexibility. Here are some key tips to help you save:
- Best times to book and fly: cheaper fares are usually available when booking at least two months in advance, although most travelers tend to book between two to eight weeks ahead. Morning departures from 5 a.m. to 12 p.m. often have lower prices and are popular, while flying on Thursday typically offers better deals, even though Friday remains the most favored travel day.
- Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
- Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
- 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.
- Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
- 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 Midway International Airport from Love Field Airport
Chicago welcomes travelers from Dallas with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:
- Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
- Car rental: Renting a car from Midway International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Midway International 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 Midway International Airport, Midway Station (a metro station) is just a short 0.2 miles away on foot, providing easy access to public transport. For those traveling by car, Chicago Ashburn Station (a train station) is approximately 4.1 miles from the airport, while Lyons Seaport (a seaport) is about 7.2 miles away.
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 December. 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 $117 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.
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 from $117 and cheap return flights $223 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 December 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 Airport |
|---|---|
Destination airport | Chicago Midway Airport |
Distance | 794 miles away |
Airlines serving | Southwest Airlines, Delta |
Popular airline | Southwest Airlines |
Roundtrip price | $223 |
Average flight time | 2 hours 44 mins |