Southwest® flights from Tulsa to Chicago-Midway from $149

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Low fares from Tulsa to Chicago-Midway

$

Tulsa (TUL)to

Chicago-Midway (MDW)
Depart: 12/03/2026

One-way

Basic

From
$149
Seen: 23 hrs ago

Tulsa (TUL)to

Chicago-Midway (MDW)
Depart: 11/21/2026

One-way

Basic

From
$149
Seen: 22 hrs ago

Tulsa (TUL)to

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

One-way

Basic

From
$149
Seen: 10 hrs ago

Tulsa (TUL)to

Chicago-Midway (MDW)
Depart: 11/23/2026

One-way

Basic

From
$149
Seen: 17 hrs ago

Tulsa (TUL)to

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

One-way

Basic

From
$149
Seen: 3 hrs ago

Tulsa (TUL)to

Chicago-Midway (MDW)
Depart: 10/22/2026

One-way

Basic

From
$149
Seen: 11 hrs ago

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Explore flights from Tulsa to Chicago-Midway

Oct 2026
From$149*
Seen: 11 hrs ago
One Way/Basic
Nov 2026
From$149*
Seen: 9 hrs ago
One Way/Basic
Dec 2026
From$149*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $149
cmp-daily-histogram-bars-legend-max-price-aria-label $349
Displaying fares for October-2026
  • TUL–MDW, 10/02/2026: From $296
    02

    Fri

    OCT

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    03

    Sat

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    04

    Sun

  • TUL–MDW, 10/05/2026: From $296
    05

    Mon

  • TUL–MDW, 10/06/2026: From $260
    06

    Tue

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    07

    Wed

  • TUL–MDW, 10/08/2026: From $296
    08

    Thu

  • TUL–MDW, 10/09/2026: From $296
    09

    Fri

  • TUL–MDW, 10/10/2026: From $260
    10

    Sat

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Sun

  • TUL–MDW, 10/12/2026: From $296
    12

    Mon

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    13

    Tue

  • TUL–MDW, 10/14/2026: From $349
    14

    Wed

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    15

    Thu

  • TUL–MDW, 10/16/2026: From $270
    16

    Fri

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    17

    Sat

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    18

    Sun

  • TUL–MDW, 10/19/2026: From $270
    19

    Mon

  • TUL–MDW, 10/20/2026: From $260
    20

    Tue

  • TUL–MDW, 10/21/2026: From $260
    21

    Wed

  • TUL–MDW, 10/22/2026: From $149
    22

    Thu

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    23

    Fri

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Sat

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    25

    Sun

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    26

    Mon

  • TUL–MDW, 10/27/2026: From $149
    27

    Tue

  • TUL–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Wed

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

    Thu

  • TUL–MDW, 10/30/2026: From $160
    30

    Fri

  • TUL–MDW, 10/31/2026: From $149
    31

    Sat

  • TUL–MDW, 11/01/2026: From $216
    01

    Sun

    NOV

    • Range$149-$349

    *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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