Southwest® flights from Tulsa to Chicago-Midway from $165

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Low fares from Tulsa to Chicago-Midway

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Tulsa (TUL)to

Chicago-Midway (MDW)
Depart: 12/30/2026

One-way

Basic

From
$165
Seen: 14 hrs ago

Tulsa (TUL)to

Chicago-Midway (MDW)
Depart: 12/23/2026

One-way

Basic

From
$165
Seen: 22 hrs ago

Tulsa (TUL)to

Chicago-Midway (MDW)
Depart: 12/19/2026

One-way

Basic

From
$165
Seen: 10 hrs ago

Tulsa (TUL)to

Chicago-Midway (MDW)
Depart: 12/08/2026

One-way

Basic

From
$165
Seen: 22 hrs ago

Tulsa (TUL)to

Chicago-Midway (MDW)
Depart: 12/02/2026

One-way

Basic

From
$165
Seen: 1 hour ago

Tulsa (TUL)to

Chicago-Midway (MDW)
Depart: 12/10/2026

One-way

Basic

From
$185
Seen: 21 hrs ago

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Explore flights from Tulsa to Chicago-Midway

Nov 2026
From$225*
Seen: 11 hrs ago
One Way/Basic
Dec 2026
From$165*
Seen: 22 hrs ago
One Way/Basic
Jan 2027
From$185*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $165
cmp-daily-histogram-bars-legend-max-price-aria-label $225
Displaying fares for November-2026
  • TUL–MDW, 11/13/2026: From $225
    13

    Fri

    NOV

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

    Sat

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

    Sun

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    16

    Mon

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    17

    Tue

  • TUL–MDW, 11/18/2026: From $225
    18

    Wed

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    19

    Thu

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    20

    Fri

  • TUL–MDW, 11/21/2026: From $225
    21

    Sat

  • TUL–MDW, 11/22/2026: From $225
    22

    Sun

  • TUL–MDW, 11/23/2026: From $225
    23

    Mon

  • TUL–MDW, 11/24/2026: From $225
    24

    Tue

  • TUL–MDW, 11/25/2026: From $225
    25

    Wed

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

    Thu

  • TUL–MDW, 11/27/2026: From $225
    27

    Fri

  • TUL–MDW, 11/28/2026: From $225
    28

    Sat

  • TUL–MDW, 11/29/2026: From $225
    29

    Sun

  • TUL–MDW, 11/30/2026: From $225
    30

    Mon

  • TUL–MDW, 12/01/2026: From $225
    01

    Tue

    DEC

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

    Wed

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

    Thu

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

    Fri

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

    Sat

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    06

    Sun

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Mon

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

    Tue

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

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

    Thu

  • TUL–MDW, 12/11/2026: From $200
    11

    Fri

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Sat

    • Range$165-$225

    *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

    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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