Southwest® flights from Cleveland to Chicago-Midway from $59

Promo Code

Low fares from Cleveland to Chicago-Midway

$

Cleveland (CLE)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$59
Seen: 23 hrs ago

Cleveland (CLE)to

Chicago-Midway (MDW)
Depart: 02/13/2027

One-way

Basic

From
$59
Seen: 13 hrs ago

Cleveland (CLE)to

Chicago-Midway (MDW)
Depart: 01/30/2027

One-way

Basic

From
$59
Seen: 9 hrs ago

Cleveland (CLE)to

Chicago-Midway (MDW)
Depart: 01/16/2027

One-way

Basic

From
$59
Seen: 2 hrs ago

Cleveland (CLE)to

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

One-way

Basic

From
$59
Seen: 20 hrs ago

Cleveland (CLE)to

Chicago-Midway (MDW)
Depart: 12/23/2026

One-way

Basic

From
$59
Seen: 22 hrs ago

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Explore flights from Cleveland to Chicago-Midway

Nov 2026
From$246*
Seen: 18 hrs ago
One Way/Basic
Dec 2026
From$59*
Seen: 22 hrs ago
One Way/Basic
Jan 2027
From$59*
Seen: 20 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $59
cmp-daily-histogram-bars-legend-max-price-aria-label $291
Displaying fares for November-2026
  • CLE–MDW, 11/11/2026: From $246
    11

    Wed

    NOV

  • CLE–MDW, 11/12/2026: From $246
    12

    Thu

  • CLE–MDW, 11/13/2026: From $246
    13

    Fri

  • CLE–MDW, 11/14/2026: From $246
    14

    Sat

  • CLE–MDW, 11/15/2026: From $246
    15

    Sun

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

    Mon

  • CLE–MDW, 11/17/2026: From $246
    17

    Tue

  • CLE–MDW, 11/18/2026: From $246
    18

    Wed

  • CLE–MDW, 11/19/2026: From $246
    19

    Thu

  • CLE–MDW, 11/20/2026: From $246
    20

    Fri

  • CLE–MDW, 11/21/2026: From $246
    21

    Sat

  • CLE–MDW, 11/22/2026: From $246
    22

    Sun

  • CLE–MDW, 11/23/2026: From $246
    23

    Mon

  • CLE–MDW, 11/24/2026: From $246
    24

    Tue

  • CLE–MDW, 11/25/2026: From $246
    25

    Wed

  • CLE–MDW, 11/26/2026: From $246
    26

    Thu

  • CLE–MDW, 11/27/2026: From $246
    27

    Fri

  • CLE–MDW, 11/28/2026: From $291
    28

    Sat

  • CLE–MDW, 11/29/2026: From $256
    29

    Sun

  • CLE–MDW, 11/30/2026: From $246
    30

    Mon

  • CLE–MDW, 12/01/2026: From $246
    01

    Tue

    DEC

  • CLE–MDW: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

  • CLE–MDW, 12/03/2026: From $95
    03

    Thu

  • CLE–MDW, 12/04/2026: From $110
    04

    Fri

  • CLE–MDW, 12/05/2026: From $59
    05

    Sat

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

    Sun

  • CLE–MDW, 12/07/2026: From $95
    07

    Mon

  • CLE–MDW, 12/08/2026: From $59
    08

    Tue

  • CLE–MDW, 12/09/2026: From $59
    09

    Wed

  • CLE–MDW, 12/10/2026: From $95
    10

    Thu

    • Range$59-$291

    *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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