Southwest® flights from Chicago-Midway to Houston Hobby from $115

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Low fares from Chicago-Midway to Houston Hobby

$

Chicago-Midway (MDW)to

Houston Hobby (HOU)
Depart: 12/16/2026

One-way

Basic

From
$115
Seen: 20 hrs ago

Chicago-Midway (MDW)to

Houston Hobby (HOU)
Depart: 12/15/2026

One-way

Basic

From
$115
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Houston Hobby (HOU)
Depart: 12/12/2026

One-way

Basic

From
$115
Seen: 9 hrs ago

Chicago-Midway (MDW)to

Houston Hobby (HOU)
Depart: 12/14/2026

One-way

Basic

From
$155
Seen: 7 hrs ago

Chicago-Midway (MDW)to

Houston Hobby (HOU)
Depart: 12/15/2026

One-way

Choice

From
$155
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Houston Hobby (HOU)
Depart: 12/12/2026

One-way

Choice

From
$155
Seen: 9 hrs ago
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Explore flights from Chicago-Midway to Houston Hobby

cmp-daily-histogram-bars-legend-min-price-aria-label $155
cmp-daily-histogram-bars-legend-max-price-aria-label $240
Displaying fares for November-2026
  • MDW–HOU, 11/12/2026: From $230
    12

    Thu

    NOV

  • MDW–HOU, 11/13/2026: From $230
    13

    Fri

  • MDW–HOU, 11/14/2026: From $230
    14

    Sat

  • MDW–HOU: cmp-view-offers-disclaimer. Find Offers
    15

    Sun

  • MDW–HOU, 11/16/2026: From $230
    16

    Mon

  • MDW–HOU, 11/17/2026: From $230
    17

    Tue

  • MDW–HOU, 11/18/2026: From $230
    18

    Wed

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

    Thu

  • MDW–HOU, 11/20/2026: From $230
    20

    Fri

  • MDW–HOU, 11/21/2026: From $230
    21

    Sat

  • MDW–HOU, 11/22/2026: From $230
    22

    Sun

  • MDW–HOU, 11/23/2026: From $230
    23

    Mon

  • MDW–HOU, 11/24/2026: From $230
    24

    Tue

  • MDW–HOU, 11/25/2026: From $240
    25

    Wed

  • MDW–HOU, 11/26/2026: From $230
    26

    Thu

  • MDW–HOU, 11/27/2026: From $235
    27

    Fri

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

    Sat

  • MDW–HOU, 11/29/2026: From $230
    29

    Sun

  • MDW–HOU, 11/30/2026: From $230
    30

    Mon

  • MDW–HOU, 12/01/2026: From $230
    01

    Tue

    DEC

  • MDW–HOU, 12/02/2026: From $165
    02

    Wed

  • MDW–HOU, 12/03/2026: From $185
    03

    Thu

  • MDW–HOU, 12/04/2026: From $200
    04

    Fri

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

    Sat

  • MDW–HOU, 12/06/2026: From $230
    06

    Sun

  • MDW–HOU, 12/07/2026: From $185
    07

    Mon

  • MDW–HOU, 12/08/2026: From $165
    08

    Tue

  • MDW–HOU, 12/09/2026: From $165
    09

    Wed

  • MDW–HOU, 12/10/2026: From $185
    10

    Thu

  • MDW–HOU, 12/11/2026: From $155
    11

    Fri

  • Range$155-$240

    Flight Details

    Departing from:
    Chicago Midway International Airport
    Arriving at:
    William P. Hobby Airport
    Average flight time:
    2 hours 35 minutes
    Distance:
    937 miles

    Explore Houston (Hobby)

    Take a flight from Chicago (Midway) to Houston (Hobby) with Southwest. Whether it’s your first time visiting or you’ve gone a hundred times, Houston always has something new to offer. Foodies enjoy the location for its diverse range of cuisine. The city has thousands of different restaurants that serve food from all over the world, although Tex-Mex is Houston’s claim to fame. For sports lovers, Houston is a dream come true. Catch a professional baseball, football, or basketball game while you’re in town and root for the home team. Is your head always in the clouds? Visit Space Center Houston to learn more about some of NASA’s most impressive rockets.

    In addition to Space Center Houston, you will find plenty of other interesting museums to visit as well. The Museum of Natural Science is home to other space station models and also some pretty cool dinos—including four T-Rexes! For those individuals who like art, the Museum of Fine Arts covers more than 6,000 years of history with approximately 64,000 works from all over the world. Talk about impressive! Do you have little ones with you? Check out the Houston Children’s Museum, which offers fun exhibits the whole family can enjoy. After all that learning, you might like to get out and soak up some Houston sunshine (and we don’t blame you!) Take a stroll through one of Houston’s beautiful parks. Or rent a bike and hit a trail—it’s a win-win, either way!

    Questions we hear the most

    The average flight time from Chicago (Midway) to Houston (Hobby) is 2 hours 35 minutes.
    There are 156 weekly flights from Chicago (Midway) to Houston (Hobby) on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Houston (Hobby) 5 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Houston (Hobby) 5 times per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Houston (Hobby) with Southwest, check out our Low Fare Calendar.
    You can rent a car at William P. Hobby Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Houston (Hobby)—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.

    Popular Flights from Chicago-Midway