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: 11/21/2026

One-way

Basic

From
$129
Seen: 23 hrs ago

Kansas City (MCI)to

Chicago (Midway) (MDW)
Depart: 11/17/2026

One-way

Basic

From
$129
Seen: 21 hrs ago

Kansas City (MCI)to

Chicago (Midway) (MDW)
Depart: 12/01/2026

One-way

Basic

From
$129
Seen: 15 hrs ago

Kansas City (MCI)to

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

One-way

Basic

From
$129
Seen: 16 hrs ago

Kansas City (MCI)to

Chicago (Midway) (MDW)
Depart: 10/07/2026

One-way

Basic

From
$129
Seen: 9 hrs ago

Kansas City (MCI)to

Chicago (Midway) (MDW)
Depart: 10/05/2026

One-way

Basic

From
$129
Seen: 12 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

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

Aug 2026
From$202*
Seen: 4 hrs ago
One Way/Basic
Sep 2026
From$129*
Seen: 23 hrs ago
One Way/Basic
Oct 2026
From$129*
Seen: 21 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $129
cmp-daily-histogram-bars-legend-max-price-aria-label $222
Displaying fares for August-2026
  • MCI–MDW, 08/26/2026: From $202
    26

    Wed

    AUG

  • MCI–MDW, 08/27/2026: From $222
    27

    Thu

  • MCI–MDW, 08/28/2026: From $222
    28

    Fri

  • MCI–MDW, 08/29/2026: From $202
    29

    Sat

  • MCI–MDW, 08/30/2026: From $222
    30

    Sun

  • MCI–MDW, 08/31/2026: From $222
    31

    Mon

  • MCI–MDW, 09/01/2026: From $202
    01

    Tue

    SEP

  • MCI–MDW, 09/02/2026: From $202
    02

    Wed

  • MCI–MDW, 09/03/2026: From $222
    03

    Thu

  • MCI–MDW, 09/04/2026: From $222
    04

    Fri

  • MCI–MDW, 09/05/2026: From $198
    05

    Sat

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

    Sun

  • MCI–MDW, 09/07/2026: From $222
    07

    Mon

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

    Tue

  • MCI–MDW, 09/09/2026: From $198
    09

    Wed

  • MCI–MDW, 09/10/2026: From $198
    10

    Thu

  • MCI–MDW, 09/11/2026: From $198
    11

    Fri

  • MCI–MDW, 09/12/2026: From $198
    12

    Sat

  • MCI–MDW: cmp-view-offers-disclaimer. Find Offers
    13

    Sun

  • MCI–MDW, 09/14/2026: From $222
    14

    Mon

  • MCI–MDW, 09/15/2026: From $129
    15

    Tue

  • MCI–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Wed

  • MCI–MDW, 09/17/2026: From $129
    17

    Thu

  • MCI–MDW, 09/18/2026: From $140
    18

    Fri

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

    Sat

  • MCI–MDW, 09/20/2026: From $190
    20

    Sun

  • MCI–MDW, 09/21/2026: From $129
    21

    Mon

  • MCI–MDW, 09/22/2026: From $129
    22

    Tue

  • MCI–MDW, 09/23/2026: From $129
    23

    Wed

  • MCI–MDW, 09/24/2026: From $129
    24

    Thu

  • MCI–MDW, 09/25/2026: From $140
    25

    Fri

    • Range$129-$222

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Kansas City