Southwest® flights from Cleveland to Chicago-Midway from $72

Promo Code

Low fares from Cleveland to Chicago-Midway

$

Cleveland (CLE)to

Chicago-Midway (MDW)
Depart: 01/17/2027

One-way

Basic

From
$72
Seen: 17 hrs ago

Cleveland (CLE)to

Chicago-Midway (MDW)
Depart: 12/07/2026

One-way

Basic

From
$72
Seen: 16 hrs ago

Cleveland (CLE)to

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

One-way

Basic

From
$72
Seen: 18 hrs ago

Cleveland (CLE)to

Chicago-Midway (MDW)
Depart: 12/04/2026

One-way

Basic

From
$72
Seen: 19 hrs ago

Cleveland (CLE)to

Chicago-Midway (MDW)
Depart: 11/22/2026

One-way

Basic

From
$72
Seen: 18 hrs ago

Cleveland (CLE)to

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

One-way

Basic

From
$72
Seen: 18 hrs ago

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Explore flights from Cleveland to Chicago-Midway

Oct 2026
From$252*
Seen: 4 hrs ago
One Way/Basic
Nov 2026
From$72*
Seen: 7 hrs ago
One Way/Basic
Dec 2026
From$72*
Seen: 10 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $72
cmp-daily-histogram-bars-legend-max-price-aria-label $297
Displaying fares for October-2026
  • CLE–MDW, 10/22/2026: From $297
    22

    Thu

    OCT

  • CLE–MDW, 10/23/2026: From $297
    23

    Fri

  • CLE–MDW, 10/24/2026: From $253
    24

    Sat

  • CLE–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Sun

  • CLE–MDW, 10/26/2026: From $297
    26

    Mon

  • CLE–MDW, 10/27/2026: From $252
    27

    Tue

  • CLE–MDW, 10/28/2026: From $252
    28

    Wed

  • CLE–MDW, 10/29/2026: From $297
    29

    Thu

  • CLE–MDW, 10/30/2026: From $297
    30

    Fri

  • CLE–MDW, 10/31/2026: From $253
    31

    Sat

  • CLE–MDW, 11/01/2026: From $297
    01

    Sun

    NOV

  • CLE–MDW, 11/02/2026: From $297
    02

    Mon

  • CLE–MDW, 11/03/2026: From $252
    03

    Tue

  • CLE–MDW, 11/04/2026: From $253
    04

    Wed

  • CLE–MDW, 11/05/2026: From $255
    05

    Thu

  • CLE–MDW, 11/06/2026: From $255
    06

    Fri

  • CLE–MDW, 11/07/2026: From $252
    07

    Sat

  • CLE–MDW, 11/08/2026: From $255
    08

    Sun

  • CLE–MDW, 11/09/2026: From $104
    09

    Mon

  • CLE–MDW, 11/10/2026: From $72
    10

    Tue

  • CLE–MDW, 11/11/2026: From $104
    11

    Wed

  • CLE–MDW, 11/12/2026: From $72
    12

    Thu

  • CLE–MDW, 11/13/2026: From $72
    13

    Fri

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

    Sat

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

    Sun

  • CLE–MDW, 11/16/2026: From $104
    16

    Mon

  • CLE–MDW, 11/17/2026: From $72
    17

    Tue

  • CLE–MDW, 11/18/2026: From $72
    18

    Wed

  • CLE–MDW, 11/19/2026: From $72
    19

    Thu

  • CLE–MDW, 11/20/2026: From $142
    20

    Fri

  • CLE–MDW, 11/21/2026: From $72
    21

    Sat

    • Range$72-$297

    *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:
    Hopkins International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    1 hour 16 minutes
    Distance:
    307 miles

    Questions we hear the most

    The average flight time from Cleveland to Chicago (Midway) is 1 hour 16 minutes.
    There are 89 weekly flights from Cleveland to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Cleveland to Chicago (Midway) 3 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Cleveland to Chicago (Midway) 3 times per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Cleveland 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 Cleveland 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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