Southwest® flights from Chicago-Midway to Dallas-Love Field from $139

Promo Code

Low fares from Chicago-Midway to Dallas-Love Field

$

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 12/03/2026

One-way

Basic

From
$139
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 11/04/2026

One-way

Basic

From
$139
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 11/26/2026

One-way

Basic

From
$139
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 11/12/2026

One-way

Basic

From
$139
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 11/07/2026

One-way

Basic

From
$139
Seen: 21 hrs ago

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 11/17/2026

One-way

Basic

From
$139
Seen: 15 hrs ago

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Explore flights from Chicago-Midway to Dallas-Love Field

Sep 2026
From$249*
Seen: 18 hrs ago
One Way/Basic
Oct 2026
From$139*
Seen: 16 hrs ago
One Way/Basic
Nov 2026
From$139*
Seen: 7 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $139
cmp-daily-histogram-bars-legend-max-price-aria-label $297
Displaying fares for September-2026
  • MDW–DAL, 09/30/2026: From $249
    30

    Wed

    SEP

  • MDW–DAL, 10/01/2026: From $297
    01

    Thu

  • MDW–DAL, 10/02/2026: From $297
    02

    Fri

  • MDW–DAL, 10/03/2026: From $249
    03

    Sat

  • MDW–DAL, 10/04/2026: From $297
    04

    Sun

  • MDW–DAL, 10/05/2026: From $297
    05

    Mon

  • MDW–DAL, 10/06/2026: From $249
    06

    Tue

  • MDW–DAL, 10/07/2026: From $249
    07

    Wed

  • MDW–DAL, 10/08/2026: From $297
    08

    Thu

  • MDW–DAL, 10/09/2026: From $297
    09

    Fri

  • MDW–DAL, 10/10/2026: From $249
    10

    Sat

  • MDW–DAL, 10/11/2026: From $297
    11

    Sun

  • MDW–DAL, 10/12/2026: From $297
    12

    Mon

  • MDW–DAL, 10/13/2026: From $249
    13

    Tue

  • MDW–DAL, 10/14/2026: From $249
    14

    Wed

  • MDW–DAL, 10/15/2026: From $286
    15

    Thu

  • MDW–DAL, 10/16/2026: From $286
    16

    Fri

  • MDW–DAL, 10/17/2026: From $249
    17

    Sat

  • MDW–DAL, 10/18/2026: From $286
    18

    Sun

  • MDW–DAL, 10/19/2026: From $286
    19

    Mon

  • MDW–DAL, 10/20/2026: From $139
    20

    Tue

  • MDW–DAL: cmp-view-offers-disclaimer. Find Offers
    21

    Wed

  • MDW–DAL, 10/22/2026: From $139
    22

    Thu

  • MDW–DAL, 10/23/2026: From $149
    23

    Fri

  • MDW–DAL, 10/24/2026: From $139
    24

    Sat

  • MDW–DAL: cmp-view-offers-disclaimer. Find Offers
    25

    Sun

  • MDW–DAL, 10/26/2026: From $139
    26

    Mon

  • MDW–DAL, 10/27/2026: From $139
    27

    Tue

  • MDW–DAL, 10/28/2026: From $139
    28

    Wed

  • MDW–DAL, 10/29/2026: From $139
    29

    Thu

    • Range$139-$297

    *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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