Southwest® flights from Chicago (Midway) to Dallas (Love Field) from $149

Promo Code

Low fares from Chicago (Midway) to Dallas (Love Field)

$

Chicago (Midway) (MDW)to

Dallas (Love Field) (DAL)
Depart: 11/19/2026

One-way

Basic

From
$149
Seen: 22 hrs ago

Chicago (Midway) (MDW)to

Dallas (Love Field) (DAL)
Depart: 10/27/2026

One-way

Basic

From
$149
Seen: 22 hrs ago

Chicago (Midway) (MDW)to

Dallas (Love Field) (DAL)
Depart: 11/23/2026

One-way

Basic

From
$149
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

Dallas (Love Field) (DAL)
Depart: 10/03/2026

One-way

Basic

From
$149
Seen: 11 hrs ago

Chicago (Midway) (MDW)to

Dallas (Love Field) (DAL)
Depart: 10/14/2026

One-way

Basic

From
$149
Seen: 19 hrs ago

Chicago (Midway) (MDW)to

Dallas (Love Field) (DAL)
Depart: 10/10/2026

One-way

Basic

From
$149
Seen: 16 hrs ago

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Explore flights from Chicago (Midway) to Dallas (Love Field)

Aug 2026
From$225*
Seen: 1 hour ago
One Way/Basic
Sep 2026
From$149*
Seen: 23 hrs ago
One Way/Basic
Oct 2026
From$149*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $149
cmp-daily-histogram-bars-legend-max-price-aria-label $277
Displaying fares for August-2026
  • MDW–DAL, 08/22/2026: From $229
    22

    Sat

    AUG

  • MDW–DAL, 08/23/2026: From $277
    23

    Sun

  • MDW–DAL, 08/24/2026: From $225
    24

    Mon

  • MDW–DAL, 08/25/2026: From $229
    25

    Tue

  • MDW–DAL, 08/26/2026: From $229
    26

    Wed

  • MDW–DAL, 08/27/2026: From $277
    27

    Thu

  • MDW–DAL, 08/28/2026: From $277
    28

    Fri

  • MDW–DAL, 08/29/2026: From $229
    29

    Sat

  • MDW–DAL, 08/30/2026: From $277
    30

    Sun

  • MDW–DAL, 08/31/2026: From $277
    31

    Mon

  • MDW–DAL, 09/01/2026: From $229
    01

    Tue

    SEP

  • MDW–DAL, 09/02/2026: From $229
    02

    Wed

  • MDW–DAL, 09/03/2026: From $266
    03

    Thu

  • MDW–DAL, 09/04/2026: From $277
    04

    Fri

  • MDW–DAL, 09/05/2026: From $166
    05

    Sat

  • MDW–DAL, 09/06/2026: From $176
    06

    Sun

  • MDW–DAL, 09/07/2026: From $266
    07

    Mon

  • MDW–DAL, 09/08/2026: From $269
    08

    Tue

  • MDW–DAL, 09/09/2026: From $166
    09

    Wed

  • MDW–DAL, 09/10/2026: From $149
    10

    Thu

  • MDW–DAL, 09/11/2026: From $162
    11

    Fri

  • MDW–DAL, 09/12/2026: From $149
    12

    Sat

  • MDW–DAL, 09/13/2026: From $240
    13

    Sun

  • MDW–DAL, 09/14/2026: From $149
    14

    Mon

  • MDW–DAL, 09/15/2026: From $149
    15

    Tue

  • MDW–DAL, 09/16/2026: From $149
    16

    Wed

  • MDW–DAL, 09/17/2026: From $149
    17

    Thu

  • MDW–DAL, 09/18/2026: From $162
    18

    Fri

  • MDW–DAL, 09/19/2026: From $159
    19

    Sat

  • MDW–DAL, 09/20/2026: From $204
    20

    Sun

  • MDW–DAL, 09/21/2026: From $149
    21

    Mon

    • Range$149-$277

    *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:
    Chicago Midway International Airport
    Arriving at:
    Dallas Love Field
    Average flight time:
    2 hours 17 minutes
    Distance:
    793 miles

    Route Information

    156† Weekly flights
    • 6‡ Nonstop flights per day Monday through Friday
    • 4‡ Nonstop flights on Saturday
    • 7‡ 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.

    Questions we hear the most

    The average flight time from Chicago (Midway) to Dallas (Love Field) is 2 hours 17 minutes.
    There are 156 weekly flights from Chicago (Midway) to Dallas (Love Field) on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Dallas (Love Field) 6 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Dallas (Love Field) 4 times per day on Saturdays and 7 times per day on Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Dallas (Love Field) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Dallas Love Field book yours with your flight.
    Yes! Flights from Chicago (Midway) to Dallas (Love Field)—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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