Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from Dallas (Love Field) to Chicago (O'Hare) now!
Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from Dallas (Love Field) to Chicago (O'Hare) now!
Dallas (Love Field), TX to Chicago (O'Hare), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 20 travel days available. Fares are updated hourly. Fares displayed on external channels may no longer be available at time of booking. To find the most updated fare, please visit Southwest.com.
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
We make bag-checking a breeze with our flexible baggage policy. Here’s how to make your journey even smoother:
Take advantage of inflight entertainment with free movies4, free live TV5, free texting6, and $8 inflight Internet7.
We also offer free sodas, coffee, and snacks8—learn more about the inflight food and beverage experience.
Have a change of travel plans? We offer free same-day standby for all fare types. This means that you can retain your current flight while listing for standby on an earlier flight. If a seat becomes available, it’s yours at no charge!
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
| Fare | Fly one-way from $89 (departing on 2/18)* |
|---|---|
| Departing from | Dallas Love Field (DAL) |
| Arriving at | Chicago O'Hare International Airport (ORD) |
| Average flight time | 2 hours 20 minutes |
| Distance | 798 miles |
| 124† | Weekly flights |
|---|---|
| 2‡ | Nonstop flights per day Monday through Friday |
| 2 ‡ | Nonstop flights on Saturday |
| 2 ‡ | Nonstop flights on Sunday |
Other popular flights from Dallas (Love Field):
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 2/1/2025 and 2/28/2025. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 2/1/2025 and 2/28/2025.
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 20 travel days available. Fares are updated hourly. Fares displayed on external channels may no longer be available at time of booking. To find the most updated fare, please visit Southwest.com.
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.
1EarlyBird Check-In® pricing starts at $15 one-way, and is subject to availability. Pricing may vary based on the popularity and length of each (one-way) flight. Please see optional travel charges for more details.
2Upgraded boarding prices and benefits are per eligible segment. Flights must be within 24 hours of departure to be eligible for upgraded boarding.
3First and second checked bags. Weight and size limits apply.
4Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
5Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
6Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
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.
8Flights traveling 175 miles or less will have only water available. Complimentary snacks are served on flights over 175 miles. If you’re flying between Hawaii and the continental U.S., you’ll have even more snacks to choose from.
9Free same-day standby: You can list for same-day standby for an earlier flight via a Southwest Customer Service Agent at the airport or the Southwest app or mobile web. You must request to be added to the same-day standby list at least 10 minutes prior to the scheduled departure of your original flight or the no-show policy will apply. If using the app or mobile web, you must list your name 30 minutes ahead of scheduled departure. You will receive a message based on the contact preference selected during booking if you are cleared on the flight. Group bookings and Unaccompanied Minors are not eligible for same-day standby. You will be required to pay any government taxes and fees associated with these itinerary changes but refunds will be provided. Your original boarding position is not guaranteed on your standby flight. Southwest Business Customers booked through travel agencies may need to see a Southwest agent at the airport for a standby listing. See Southwest.com/standby for more details.