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

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Low fares from Tulsa to Chicago (Midway)

$

Tulsa (TUL)to

Chicago (Midway) (MDW)
Depart: 11/16/2026

One-way

Basic

From
$89
Seen: 12 hrs ago

Tulsa (TUL)to

Chicago (Midway) (MDW)
Depart: 10/27/2026

One-way

Basic

From
$89
Seen: 13 hrs ago

Tulsa (TUL)to

Chicago (Midway) (MDW)
Depart: 10/28/2026

One-way

Basic

From
$89
Seen: 10 hrs ago

Tulsa (TUL)to

Chicago (Midway) (MDW)
Depart: 09/30/2026

One-way

Basic

From
$89
Seen: 4 hrs ago

Tulsa (TUL)to

Chicago (Midway) (MDW)
Depart: 10/31/2026

One-way

Basic

From
$89
Seen: 5 hrs ago

Tulsa (TUL)to

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

One-way

Basic

From
$89
Seen: 3 hrs ago

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Explore flights from Tulsa to Chicago (Midway)

Aug 2026
From$240*
Seen: 23 hrs ago
One Way/Basic
Sep 2026
From$89*
Seen: 20 hrs ago
One Way/Basic
Oct 2026
From$89*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $89
cmp-daily-histogram-bars-legend-max-price-aria-label $276
Displaying fares for August-2026
  • TUL–MDW, 08/22/2026: From $240
    22

    Sat

    AUG

  • TUL–MDW, 08/23/2026: From $276
    23

    Sun

  • TUL–MDW, 08/24/2026: From $276
    24

    Mon

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Tue

  • TUL–MDW, 08/26/2026: From $240
    26

    Wed

  • TUL–MDW, 08/27/2026: From $276
    27

    Thu

  • TUL–MDW, 08/28/2026: From $276
    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 $276
    31

    Mon

  • TUL–MDW, 09/01/2026: From $240
    01

    Tue

    SEP

  • TUL–MDW, 09/02/2026: From $240
    02

    Wed

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    03

    Thu

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    04

    Fri

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Sat

  • TUL–MDW, 09/06/2026: From $190
    06

    Sun

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    07

    Mon

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Tue

  • TUL–MDW, 09/09/2026: From $190
    09

    Wed

  • TUL–MDW, 09/10/2026: From $190
    10

    Thu

  • TUL–MDW, 09/11/2026: From $107
    11

    Fri

  • TUL–MDW, 09/12/2026: From $89
    12

    Sat

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    13

    Sun

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

  • TUL–MDW, 09/15/2026: From $89
    15

    Tue

  • TUL–MDW, 09/16/2026: From $89
    16

    Wed

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    17

    Thu

  • TUL–MDW, 09/18/2026: From $107
    18

    Fri

  • TUL–MDW, 09/19/2026: From $89
    19

    Sat

  • TUL–MDW, 09/20/2026: From $196
    20

    Sun

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

    Mon

    • Range$89-$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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