Southwest® flights from Kansas City to Chicago (O'Hare)

Promo Code

Low fares from Kansas City to Chicago (O'Hare)

$

Kansas City (MCI)to

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

One-way

Basic

From
$109
Seen: 11 hrs ago

Kansas City (MCI)to

Chicago (Midway) (MDW)
Depart: 09/11/2026

One-way

Basic

From
$109
Seen: 15 hrs ago

Kansas City (MCI)to

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Basic

From
$109
Seen: 4 hrs ago

Kansas City (MCI)to

Chicago (Midway) (MDW)
Depart: 10/20/2026

One-way

Basic

From
$128
Seen: 22 hrs ago

Kansas City (MCI)to

Chicago (Midway) (MDW)
Depart: 11/12/2026

One-way

Basic

From
$128
Seen: 17 hrs ago

Kansas City (MCI)to

Chicago (Midway) (MDW)
Depart: 10/29/2026

One-way

Basic

From
$128
Seen: 22 hrs ago

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Explore flights from Kansas City to Chicago (O'Hare)

Aug 2026
From$128*
Seen: 9 hrs ago
One Way/Basic
Sep 2026
From$109*
Seen: 11 hrs ago
One Way/Basic
Oct 2026
From$109*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $109
cmp-daily-histogram-bars-legend-max-price-aria-label $240
Displaying fares for August-2026
  • MCI–MDW, 08/06/2026: From $230
    06

    Thu

    AUG

  • MCI–MDW, 08/07/2026: From $222
    07

    Fri

  • MCI–MDW, 08/08/2026: From $215
    08

    Sat

  • MCI–MDW, 08/09/2026: From $240
    09

    Sun

  • MCI–MDW, 08/10/2026: From $222
    10

    Mon

  • MCI–MDW, 08/11/2026: From $215
    11

    Tue

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

    Wed

  • MCI–MDW, 08/13/2026: From $222
    13

    Thu

  • MCI–MDW, 08/14/2026: From $230
    14

    Fri

  • MCI–MDW, 08/15/2026: From $215
    15

    Sat

  • MCI–MDW, 08/16/2026: From $230
    16

    Sun

  • MCI–MDW, 08/17/2026: From $230
    17

    Mon

  • MCI–MDW, 08/18/2026: From $215
    18

    Tue

  • MCI–MDW, 08/19/2026: From $202
    19

    Wed

  • MCI–MDW, 08/20/2026: From $230
    20

    Thu

  • MCI–MDW, 08/21/2026: From $230
    21

    Fri

  • MCI–MDW, 08/22/2026: From $215
    22

    Sat

  • MCI–MDW, 08/23/2026: From $230
    23

    Sun

  • MCI–MDW, 08/24/2026: From $230
    24

    Mon

  • MCI–MDW, 08/25/2026: From $215
    25

    Tue

  • MCI–MDW, 08/26/2026: From $128
    26

    Wed

  • MCI–MDW, 08/27/2026: From $128
    27

    Thu

  • MCI–MDW, 08/28/2026: From $154
    28

    Fri

  • MCI–MDW, 08/29/2026: From $128
    29

    Sat

  • MCI–MDW, 08/30/2026: From $190
    30

    Sun

  • MCI–MDW, 08/31/2026: From $128
    31

    Mon

  • MCI–MDW, 09/01/2026: From $128
    01

    Tue

    SEP

  • MCI–MDW, 09/02/2026: From $128
    02

    Wed

  • MCI–MDW, 09/03/2026: From $128
    03

    Thu

  • MCI–MDW, 09/04/2026: From $154
    04

    Fri

  • MCI–MDW, 09/05/2026: From $109
    05

    Sat

    • Range$109-$240

    *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:
    Kansas City International Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    403 miles

    Route Information

    129† 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 129 weekly flights from Kansas City to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Kansas City 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 Kansas City 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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