When the Windy City calls, you can find direct flights from Dallas (Love Field) to Chicago (Midway) at Southwest Airlines®. Going from D-Town to the City of the Big Shoulders is straightforward with Southwest®—and you'll find flights at Midwest-nice prices. Book with confidence no matter if you're traveling for business, pleasure, or a bit of both. Does your Chi-Town visit have flexible dates? Search for your Dallas (Love Field) to Chicago (Midway) flight with our Low Fare Calendar and discover a range of rates on your flight. Explore Southwest Vacations® and see opportunities for savings on flights, hotels, rental cars, and more.
Check out Dallas (Love Field) to Chicago (Midway) flights and book yours today!
Dallas (Love Field), TX to Chicago (Midway), IL
departing on 12/05
one-way starting at*$50
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 25 travel days available.
Middle seats open through November 30
Full exchange of fresh, outdoor air every 2-3 minutes while inflight
Face coverings required
Average flight time: 2 hours 10 minutes
Departing from: Dallas Love Field (DAL)
Arriving at: Chicago Midway International Airport (MDW)
Nonstop flightsper day
Other popular flights from DallasView our interactive map
†Based on DOT published scheduled average flights Monday-Friday between 10/9/2020 and 12/31/2020, as of 10/9/2020.
Those in the know will tell you that both Dallas and Chicago are cities comprised of sides and neighborhoods. Distinct. Unique. Each one full of the possibility for adventure and discovery. When your Southwest flight to Chicago (Midway) lands, you can hop on the Orange Line of the CTA and start exploring immediately. Half an hour aboard will land you in the Loop—what Chicagoans call their downtown—where you can transfer to any other rail line you'd like (or hop aboard a bus). The neighborhoods await—will you explore Pilsen, or Dunning, or Hyde Park?
Chicago is a noted destination for foodie tourists, and with good reason: From Michelin-starred haute cuisine eateries to hole-in-the-wall neighborhood joints, there's something for everyone. But beware: Know that deep dish pizza is just for when your least-cool relatives come to town, and that a Chicago-style hot dog demands that you never, ever look at ketchup. (Some hot dog stands will turn you away if you even ask for it!)
Chicago is a big sports town year round. Take in a baseball game—either the north side team or the south side team, we won't tell you which home team to root for—or check out whatever's happening at the stadium shared by the basketball and hockey teams. The lakefront landmark where the football team plays is a real sight to see. Sports not your thing? Take in a play, an improv show, some standup comedy, staged storytelling, a concert, the symphony—the list goes on. There really is something for everyone in Chi-Town.
One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.
Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest® pet policy.
Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
We know that a memorable trip from Dallas to Chicago (and back again, or beyond) is made of more than cheap flights. Thankfully, Southwest has more to offer than cheap fares. Find out more about Southwest Travel Experience while you book your Dallas (Love Field) to Chicago (Midway) flight.
No matter where you're headed, traveling with Southwest Airlines is simple and straightforward. When you search for and book your next flight, you know there will be no hidden fees, and always low fares—that's our Transfarency® promise. Stay up to date with our latest flight deals: Enroll in our Click 'N Save® emails. Looking for tours, activities, and more hidden gems? Check out Southwest Airlines® Experiences and earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
How long is the flight from Dallas (Love Field) to Chicago (Midway)?
The average flight time from Dallas (Love Field) to Chicago (Midway) is 2 hours 10 minutes.
How many Southwest flights from Dallas (Love Field) to Chicago (Midway) occur daily?
There are 19 flights daily from Dallas (Love Field) to Chicago (Midway) on Southwest Airlines.
Does Southwest fly nonstop from Dallas (Love Field) to Chicago (Midway)?
Southwest flies nonstop from Dallas (Love Field) to Chicago (Midway) 6 times daily.
What day is it cheapest to fly from Dallas (Love Field) to Chicago (Midway)?
To find the cheapest day and time to fly Dallas (Love Field) to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
Can I rent a car at Chicago Midway International Airport?
You can rent a car at Chicago Midway International Airport—book yours with your flight.
Can I change my flight reservation for my flight from Dallas (Love Field) to Chicago (Midway)?
Yes! Flights from Dallas (Love Field) to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Where can I find the status of my flight from Dallas (Love Field) to Chicago (Midway)?
Check the status of your upcoming Southwest flight here.
Where can I find answers to other questions about flying from Dallas (Love Field) to Chicago (Midway) with Southwest?
Check out the Southwest Airlines® FAQs for answers about everything Southwest.