Southwest® flights from Tulsa to Chicago (Midway) from $89

Promo Code

Low fares from Tulsa to Chicago (Midway)

$

Tulsa (TUL)to

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

One-way

Basic

From
$89
Seen: 7 hrs ago

Tulsa (TUL)to

Chicago (Midway) (MDW)
Depart: 09/16/2026

One-way

Basic

From
$107
Seen: 20 hrs ago

Tulsa (TUL)to

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

One-way

Basic

From
$107
Seen: 6 hrs ago

Tulsa (TUL)to

Chicago (Midway) (MDW)
Depart: 08/22/2026

One-way

Basic

From
$107
Seen: 7 hrs ago

Tulsa (TUL)to

Chicago (Midway) (MDW)
Depart: 10/21/2026

One-way

Basic

From
$107
Seen: 6 hrs ago

Tulsa (TUL)to

Chicago (Midway) (MDW)
Depart: 09/17/2026

One-way

Basic

From
$107
Seen: 3 hrs ago

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Explore flights from Tulsa to Chicago (Midway)

Aug 2026
From$107*
Seen: 2 hrs ago
One Way/Basic
Sep 2026
From$89*
Seen: 7 hrs ago
One Way/Basic
Oct 2026
From$107*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $107
cmp-daily-histogram-bars-legend-max-price-aria-label $276
Displaying fares for August-2026
  • TUL–MDW, 08/02/2026: From $276
    02

    Sun

    AUG

  • TUL–MDW, 08/03/2026: From $276
    03

    Mon

  • TUL–MDW, 08/04/2026: From $240
    04

    Tue

  • TUL–MDW, 08/05/2026: From $240
    05

    Wed

  • TUL–MDW, 08/06/2026: From $276
    06

    Thu

  • TUL–MDW, 08/07/2026: From $276
    07

    Fri

  • TUL–MDW, 08/08/2026: From $240
    08

    Sat

  • TUL–MDW, 08/09/2026: From $276
    09

    Sun

  • TUL–MDW, 08/10/2026: From $276
    10

    Mon

  • TUL–MDW, 08/11/2026: From $240
    11

    Tue

  • TUL–MDW, 08/12/2026: From $240
    12

    Wed

  • TUL–MDW, 08/13/2026: From $276
    13

    Thu

  • TUL–MDW, 08/14/2026: From $250
    14

    Fri

  • TUL–MDW, 08/15/2026: From $240
    15

    Sat

  • TUL–MDW, 08/16/2026: From $250
    16

    Sun

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    17

    Mon

  • TUL–MDW, 08/18/2026: From $240
    18

    Tue

  • TUL–MDW, 08/19/2026: From $240
    19

    Wed

  • TUL–MDW, 08/20/2026: From $250
    20

    Thu

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

    Fri

  • TUL–MDW, 08/22/2026: From $107
    22

    Sat

  • TUL–MDW, 08/23/2026: From $228
    23

    Sun

  • TUL–MDW, 08/24/2026: From $107
    24

    Mon

  • TUL–MDW, 08/25/2026: From $107
    25

    Tue

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    26

    Wed

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

    Thu

  • TUL–MDW, 08/28/2026: From $152
    28

    Fri

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Sat

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

  • TUL–MDW, 08/31/2026: From $107
    31

    Mon

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

    • Range$107-$276

    *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:
    Tulsa International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    1 hour 46 minutes
    Distance:
    583 miles

    Route Information

    150† Weekly flights
    • 1‡ Nonstop flight per day Monday through Friday
    • 1‡ Nonstop flight on Saturday
    • 2‡ 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 Tulsa to Chicago (Midway) is 1 hour 46 minutes.
    There are 150 weekly flights from Tulsa to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Tulsa to Chicago (Midway) once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Tulsa to Chicago (Midway) once per day on Saturdays and 2 times per day on Sundays.
    To find the lowest fares by day and time to fly Tulsa to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Tulsa to Chicago (Midway)—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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