Southwest® flights from Houston (Hobby) to Chicago (O'Hare)

Promo Code

Low fares from Houston (Hobby) to Chicago (O'Hare)

$

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 09/06/2026

One-way

Basic

From
$105
Seen: 17 hrs ago

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Basic

From
$105
Seen: 16 hrs ago

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 09/11/2026

One-way

Basic

From
$105
Seen: 21 hrs ago

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 09/05/2026

One-way

Basic

From
$115
Seen: 23 hrs ago

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 08/29/2026

One-way

Basic

From
$118
Seen: 20 hrs ago

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 10/14/2026

One-way

Basic

From
$118
Seen: 19 hrs ago

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Explore flights from Houston (Hobby) to Chicago (O'Hare)

Aug 2026
From$118*
Seen: 16 hrs ago
One Way/Basic
Sep 2026
From$105*
Seen: 17 hrs ago
One Way/Basic
Oct 2026
From$105*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $118
cmp-daily-histogram-bars-legend-max-price-aria-label $280
Displaying fares for August-2026
  • HOU–MDW, 08/05/2026: From $229
    05

    Wed

    AUG

  • HOU–MDW, 08/06/2026: From $277
    06

    Thu

  • HOU–MDW, 08/07/2026: From $277
    07

    Fri

  • HOU–MDW, 08/08/2026: From $229
    08

    Sat

  • HOU–MDW, 08/09/2026: From $277
    09

    Sun

  • HOU–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Mon

  • HOU–MDW, 08/11/2026: From $229
    11

    Tue

  • HOU–MDW, 08/12/2026: From $229
    12

    Wed

  • HOU–MDW, 08/13/2026: From $277
    13

    Thu

  • HOU–MDW, 08/14/2026: From $277
    14

    Fri

  • HOU–MDW, 08/15/2026: From $229
    15

    Sat

  • HOU–MDW, 08/16/2026: From $277
    16

    Sun

  • HOU–MDW, 08/17/2026: From $277
    17

    Mon

  • HOU–MDW, 08/18/2026: From $229
    18

    Tue

  • HOU–MDW, 08/19/2026: From $229
    19

    Wed

  • HOU–MDW, 08/20/2026: From $270
    20

    Thu

  • HOU–MDW, 08/21/2026: From $280
    21

    Fri

  • HOU–MDW, 08/22/2026: From $229
    22

    Sat

  • HOU–MDW, 08/23/2026: From $270
    23

    Sun

  • HOU–MDW, 08/24/2026: From $270
    24

    Mon

  • HOU–MDW, 08/25/2026: From $118
    25

    Tue

  • HOU–MDW, 08/26/2026: From $118
    26

    Wed

  • HOU–MDW, 08/27/2026: From $128
    27

    Thu

  • HOU–MDW, 08/28/2026: From $146
    28

    Fri

  • HOU–MDW, 08/29/2026: From $118
    29

    Sat

  • HOU–MDW, 08/30/2026: From $236
    30

    Sun

  • HOU–MDW, 08/31/2026: From $118
    31

    Mon

  • HOU–MDW, 09/01/2026: From $118
    01

    Tue

    SEP

  • HOU–MDW, 09/02/2026: From $118
    02

    Wed

  • HOU–MDW, 09/03/2026: From $184
    03

    Thu

  • HOU–MDW, 09/04/2026: From $184
    04

    Fri

    • Range$118-$280

    *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:
    William P. Hobby Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    945 miles

    Route Information

    154† Weekly flights

    † 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

    There are 154 weekly flights from Houston (Hobby) to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Houston (Hobby) to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Houston (Hobby) to Chicago (O'Hare)—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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