Southwest® flights from Tulsa to Chicago (O'Hare)

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Low fares from Tulsa to Chicago (O'Hare)

$

Tulsa (TUL)to

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

One-way

Basic

From
$89
Seen: 22 hrs ago

Tulsa (TUL)to

Chicago (Midway) (MDW)
Depart: 10/01/2026

One-way

Basic

From
$89
Seen: 17 hrs ago

Tulsa (TUL)to

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

One-way

Basic

From
$89
Seen: 16 hrs ago

Tulsa (TUL)to

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

One-way

Basic

From
$89
Seen: 11 hrs ago

Tulsa (TUL)to

Chicago (Midway) (MDW)
Depart: 09/14/2026

One-way

Basic

From
$89
Seen: 8 hrs ago

Tulsa (TUL)to

Chicago (Midway) (MDW)
Depart: 09/29/2026

One-way

Basic

From
$89
Seen: 5 hrs ago

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Explore flights from Tulsa to Chicago (O'Hare)

Aug 2026
From$240*
Seen: 17 hrs ago
One Way/Basic
Sep 2026
From$89*
Seen: 23 hrs ago
One Way/Basic
Oct 2026
From$89*
Seen: 12 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $89
cmp-daily-histogram-bars-legend-max-price-aria-label $286
Displaying fares for August-2026
  • TUL–MDW, 08/25/2026: From $240
    25

    Tue

    AUG

  • 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, 08/29/2026: From $240
    29

    Sat

  • TUL–MDW, 08/30/2026: From $276
    30

    Sun

  • TUL–MDW, 08/31/2026: From $286
    31

    Mon

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

    Tue

    SEP

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

    Wed

  • TUL–MDW, 09/03/2026: From $276
    03

    Thu

  • TUL–MDW, 09/04/2026: From $276
    04

    Fri

  • TUL–MDW, 09/05/2026: From $190
    05

    Sat

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

    Sun

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

    Fri

  • TUL–MDW, 09/12/2026: From $190
    12

    Sat

  • TUL–MDW, 09/13/2026: From $250
    13

    Sun

  • TUL–MDW, 09/14/2026: From $89
    14

    Mon

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

    Tue

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

    Wed

  • TUL–MDW, 09/17/2026: From $89
    17

    Thu

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

    Fri

  • TUL–MDW, 09/19/2026: From $129
    19

    Sat

  • TUL–MDW, 09/20/2026: From $141
    20

    Sun

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

    Mon

  • TUL–MDW, 09/22/2026: From $89
    22

    Tue

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

    Wed

  • TUL–MDW, 09/24/2026: From $89
    24

    Thu

    • Range$89-$286

    *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:
    O'Hare International Airport
    Distance:
    585 miles

    Route Information

    78† 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 78 weekly flights from Tulsa to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Tulsa 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 Tulsa 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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