Ready to wing your way to the Windy City? Southwest Airlines is ready to get you on your way. Southwest is offering flights from Dallas Love Field to Chicago O’Hare International Airport with prices that are hard to beat. If you have a wide travel window, explore our Low Fare Calendar to find the lowest available fares inside your travel dates. Make the most of your reservation with package deals on flights, hotels, rental cars, and more from Southwest Vacations®.
See why the Second City should be first on your list of places to visit.
Dallas (Love Field), TX to Chicago (O'Hare), IL
departing on 4/8
one-way starting at*$103
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 17 travel days available.
|Dallas Love Field (DAL)
|Chicago O'Hare International Airport (ORD)
|Average flight time
|2 hours 21 minutes
|Nonstop flights per day Monday through Friday
|Nonstop flights on Saturday
|Nonstop flights on Sunday
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 3/1/2024 and 3/31/2024. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 3/1/2024 and 3/31/2024.
Chicago is truly one of the nation’s great cities, with awe-inspiring architecture, a wealth of cultural opportunities, and world-class nightlife. Whatever you’re into, you’ll find it in Chicago.
A thriving metropolis situated on the shore of picturesque Lake Michigan, Chicago’s waterfront location offers a wide array of activities and attractions to explore. Downtown Chicago is the cultural center of the city as well as the site of Grant Park. Here, visitors can experience sprawling lawns, colorful flowers, selfie-worthy fountains, several fascinating public art installations, and the captivating Cloud Gate sculpture, affectionately called The Bean for its shape.
Head south of the Loop to get acquainted with aquatic life at the Shedd Aquarium. Enjoy its polar playroom, the stingray touch exhibit, and watching the majestic dolphins and beluga whales in the Abbot Oceanarium. It’s also located right near the Adler Planetarium and Field Museum of Natural History. It’s easy to spend the day enjoying the splendor of the rivers and oceans, outer space, and nature, all while remaining indoors, which is desirable during the winter months.
When the sun goes down, the town doesn’t stop. There are a slew of theatre, live music, comedy, and dining options available to you. Dive into Chicago’s legendary blues scene. Check out the stand-up and improv comedy skits of the stars of today. And in addition to Chicago-style pizza (thin crust tavern cut or deep dish), you’re sure to find a restaurant to please any of the most adventurous or picky of palates.
Whether you want to do everything or do nothing, Chicago has big-city feel combined with Midwestern hospitality. It’s all there waiting for you.
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.
At Southwest, we know it takes more than great deals on Chicago (O'Hare) 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 (O'Hare) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Dallas Love Field to Chicago O'Hare 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 (O'Hare), 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.
5Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
6Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
7Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.