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 12/28
one-way starting at*$163
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 165 travel days available.
|Departing from||Dallas Love Field (DAL)|
|Arriving at||Chicago Midway International Airport (MDW)|
|Average flight time||2 hours 9 minutes|
|6‡||Nonstop flights per day Monday through Friday|
|5‡||Nonstop flights on Saturday|
|6‡||Nonstop flights on Sunday|
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 12/1/2022 and 12/31/2022. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 12/1/2022 and 12/31/2022.
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.
Chicago Midway International Airport is a quick 30-minute 'L' ride from downtown Chicago. Get going—adventure awaits.
At Southwest, we know it takes more than great deals on Chicago (Midway) airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Dallas (Love Field) to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Dallas Love Field to Chicago Midway International Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Chicago (Midway), know that you won’t be surprised at checkout. Low fares and no hidden fees. That's Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? Sign up to receive email from us. Book your flight today and know that you'll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Available only on WiFi-enabled aircraft. Limited-time offer. Where available.
6Internet access for $8 a day, per device. In order to provide the best experience, we block access to certain high-bandwidth applications, websites, and video conferencing services, including, but not limited to, Netflix, HBO Max, Zoom, and Microsoft Teams. In consideration of the public environment onboard, we also block potentially offensive online content.