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!
Average Flight Time: 2 hours 10 minutes
Departing from: Dallas Love Field (DAL)
Arriving at: Chicago Midway International Airport (MDW)
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® when you book.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.