Southwest® flights from Dallas (Love Field) to Chicago (O'Hare) from $100

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Low fares from Dallas (Love Field) to Chicago (O'Hare)

$

Dallas (Love Field) (DAL)to

Chicago (Midway) (MDW)
Depart: 06/03/2026

One-way

Basic

From
$100
Seen: 10 hrs ago

Dallas (Love Field) (DAL)to

Chicago (Midway) (MDW)
Depart: 04/29/2026

One-way

Basic

From
$100
Seen: 10 hrs ago

Dallas (Love Field) (DAL)to

Chicago (Midway) (MDW)
Depart: 05/12/2026

One-way

Basic

From
$100
Seen: 4 hrs ago

Dallas (Love Field) (DAL)to

Chicago (Midway) (MDW)
Depart: 05/05/2026

One-way

Basic

From
$100
Seen: 10 hrs ago

Dallas (Love Field) (DAL)to

Chicago (Midway) (MDW)
Depart: 05/16/2026

One-way

Basic

From
$100
Seen: 10 hrs ago

Dallas (Love Field) (DAL)to

Chicago (Midway) (MDW)
Depart: 05/04/2026

One-way

Basic

From
$100
Seen: 11 hrs ago

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Explore flights from Dallas (Love Field) to Chicago (O'Hare)

Apr 2026
From$100*
Seen: 10 hrs ago
One Way/Basic
May 2026
From$100*
Seen: 10 hrs ago
One Way/Basic
Jun 2026
From$100*
Seen: 6 hrs ago
One Way/Basic
$100
$199
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    • Range$100-$199

    *Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

    Flight Details

    Departing from:
    Dallas Love Field
    Arriving at:
    O'Hare International Airport
    Average flight time:
    2 hours 25 minutes
    Distance:
    798 miles

    Route Information

    123† Weekly flights
    • 2‡ Nonstop flights per day Monday through Friday
    • 2‡ Nonstop flights on Saturday
    • 3‡ Nonstop flights on Sunday

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Explore Chicago (O'Hare)

    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.

    Questions we hear the most

    The average flight time from Dallas (Love Field) to Chicago (O'Hare) is 2 hours 25 minutes.
    There are 123 weekly flights from Dallas (Love Field) to Chicago (O'Hare) on Southwest Airlines.
    Yes, Southwest flies nonstop from Dallas (Love Field) to Chicago (O'Hare) 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Dallas (Love Field) to Chicago (O'Hare) 2 times per day on Saturdays and 3 times per day on Sundays.
    To find the lowest fares by day and time to fly Dallas (Love Field) to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Dallas (Love Field) to Chicago (O'Hare)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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