Southwest® flights from Chicago-Midway to Dallas-Love Field from $129

Promo Code

Low fares from Chicago-Midway to Dallas-Love Field

$

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 10/26/2026

One-way

Basic

From
$129
Seen: 21 hrs ago

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 12/08/2026

One-way

Basic

From
$129
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 10/08/2026

One-way

Basic

From
$129
Seen: 9 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$129
Seen: 9 hrs ago

Chicago-Midway (MDW)to

Dallas-Love Field (DAL)
Depart: 12/09/2026

One-way

Basic

From
$129
Seen: 8 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$129
Seen: 8 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Chicago-Midway to Dallas-Love Field

Sep 2026
From$129*
Seen: 3 hrs ago
One Way/Basic
Oct 2026
From$129*
Seen: 8 hrs ago
One Way/Basic
Nov 2026
From$129*
Seen: 10 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $129
cmp-daily-histogram-bars-legend-max-price-aria-label $287
Displaying fares for September-2026
  • MDW–DAL, 09/10/2026: From $287
    10

    Thu

    SEP

  • MDW–DAL, 09/11/2026: From $287
    11

    Fri

  • MDW–DAL, 09/12/2026: From $239
    12

    Sat

  • MDW–DAL, 09/13/2026: From $287
    13

    Sun

  • MDW–DAL, 09/14/2026: From $287
    14

    Mon

  • MDW–DAL, 09/15/2026: From $239
    15

    Tue

  • MDW–DAL, 09/16/2026: From $239
    16

    Wed

  • MDW–DAL, 09/17/2026: From $287
    17

    Thu

  • MDW–DAL, 09/18/2026: From $287
    18

    Fri

  • MDW–DAL, 09/19/2026: From $239
    19

    Sat

  • MDW–DAL, 09/20/2026: From $287
    20

    Sun

  • MDW–DAL, 09/21/2026: From $287
    21

    Mon

  • MDW–DAL, 09/22/2026: From $239
    22

    Tue

  • MDW–DAL, 09/23/2026: From $239
    23

    Wed

  • MDW–DAL, 09/24/2026: From $276
    24

    Thu

  • MDW–DAL, 09/25/2026: From $276
    25

    Fri

  • MDW–DAL, 09/26/2026: From $239
    26

    Sat

  • MDW–DAL: cmp-view-offers-disclaimer. Find Offers
    27

    Sun

  • MDW–DAL, 09/28/2026: From $276
    28

    Mon

  • MDW–DAL, 09/29/2026: From $239
    29

    Tue

  • MDW–DAL, 09/30/2026: From $129
    30

    Wed

  • MDW–DAL, 10/01/2026: From $129
    01

    Thu

    OCT

  • MDW–DAL, 10/02/2026: From $139
    02

    Fri

  • MDW–DAL, 10/03/2026: From $129
    03

    Sat

  • MDW–DAL, 10/04/2026: From $250
    04

    Sun

  • MDW–DAL, 10/05/2026: From $129
    05

    Mon

  • MDW–DAL, 10/06/2026: From $129
    06

    Tue

  • MDW–DAL, 10/07/2026: From $129
    07

    Wed

  • MDW–DAL, 10/08/2026: From $129
    08

    Thu

  • MDW–DAL, 10/09/2026: From $139
    09

    Fri

    • Range$129-$287

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Chicago-Midway