Southwest® flights from Chicago-Midway to Dallas-Love Field from $105

Promo Code

Low fares from Chicago-Midway to Dallas-Love Field

$

Chicago-Midway (MDW)to

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

One-way

Basic

From
$105
Seen: 14 hrs ago

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 12/16/2026

One-way

Basic

From
$110
Seen: 2 hrs ago

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 12/15/2026

One-way

Basic

From
$110
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 01/13/2027

One-way

Basic

From
$128
Seen: 23 hrs ago

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 02/17/2027

One-way

Basic

From
$128
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 01/27/2027

One-way

Basic

From
$128
Seen: 18 hrs ago

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Explore flights from Chicago-Midway to Dallas-Love Field

Nov 2026
From$220*
Seen: 12 hrs ago
One Way/Basic
Dec 2026
From$105*
Seen: 14 hrs ago
One Way/Basic
Jan 2027
From$128*
Seen: 20 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $155
cmp-daily-histogram-bars-legend-max-price-aria-label $376
Displaying fares for November-2026
  • MDW–DAL, 11/11/2026: From $220
    11

    Wed

    NOV

  • MDW–DAL, 11/12/2026: From $220
    12

    Thu

  • MDW–DAL, 11/13/2026: From $220
    13

    Fri

  • MDW–DAL, 11/14/2026: From $220
    14

    Sat

  • MDW–DAL, 11/15/2026: From $220
    15

    Sun

  • MDW–DAL, 11/16/2026: From $220
    16

    Mon

  • MDW–DAL, 11/17/2026: From $220
    17

    Tue

  • MDW–DAL, 11/18/2026: From $220
    18

    Wed

  • MDW–DAL, 11/19/2026: From $230
    19

    Thu

  • MDW–DAL, 11/20/2026: From $220
    20

    Fri

  • MDW–DAL, 11/21/2026: From $220
    21

    Sat

  • MDW–DAL, 11/22/2026: From $376
    22

    Sun

  • MDW–DAL, 11/23/2026: From $220
    23

    Mon

  • MDW–DAL, 11/24/2026: From $220
    24

    Tue

  • MDW–DAL, 11/25/2026: From $230
    25

    Wed

  • MDW–DAL, 11/26/2026: From $220
    26

    Thu

  • MDW–DAL, 11/27/2026: From $220
    27

    Fri

  • MDW–DAL, 11/28/2026: From $230
    28

    Sat

  • MDW–DAL, 11/29/2026: From $294
    29

    Sun

  • MDW–DAL, 11/30/2026: From $220
    30

    Mon

  • MDW–DAL, 12/01/2026: From $220
    01

    Tue

    DEC

  • MDW–DAL, 12/02/2026: From $155
    02

    Wed

  • MDW–DAL, 12/03/2026: From $175
    03

    Thu

  • MDW–DAL, 12/04/2026: From $190
    04

    Fri

  • MDW–DAL, 12/05/2026: From $165
    05

    Sat

  • MDW–DAL, 12/06/2026: From $220
    06

    Sun

  • MDW–DAL, 12/07/2026: From $175
    07

    Mon

  • MDW–DAL, 12/08/2026: From $155
    08

    Tue

  • MDW–DAL, 12/09/2026: From $155
    09

    Wed

  • MDW–DAL, 12/10/2026: From $175
    10

    Thu

    • Range$155-$376

    *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

    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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