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

Promo Code

Low fares from Chicago-Midway to Cleveland

$

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 12/12/2026

One-way

Basic

From
$59
Seen: 21 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 02/16/2027

One-way

Basic

From
$59
Seen: 14 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 02/09/2027

One-way

Basic

From
$59
Seen: 4 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 02/06/2027

One-way

Basic

From
$59
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 01/16/2027

One-way

Basic

From
$59
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 01/09/2027

One-way

Basic

From
$59
Seen: 18 hrs ago

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Explore flights from Chicago-Midway to Cleveland

Nov 2026
From$246*
Seen: 13 hrs ago
One Way/Basic
Dec 2026
From$59*
Seen: 13 hrs ago
One Way/Basic
Jan 2027
From$59*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $59
cmp-daily-histogram-bars-legend-max-price-aria-label $246
Displaying fares for November-2026
  • MDW–CLE, 11/12/2026: From $246
    12

    Thu

    NOV

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

    Fri

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

    Sat

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

    Sun

  • MDW–CLE, 11/16/2026: From $246
    16

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

  • MDW–CLE: cmp-view-offers-disclaimer. Find Offers
    28

    Sat

  • MDW–CLE, 11/29/2026: From $246
    29

    Sun

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

    Mon

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

    Tue

    DEC

  • MDW–CLE, 12/02/2026: From $59
    02

    Wed

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

    Thu

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

    Fri

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

    Sat

  • MDW–CLE, 12/06/2026: From $220
    06

    Sun

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

    Mon

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

    Tue

  • MDW–CLE: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

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

    Thu

  • MDW–CLE, 12/11/2026: From $110
    11

    Fri

    • Range$59-$246

    *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:
    Chicago Midway International Airport
    Arriving at:
    Hopkins International Airport
    Average flight time:
    1 hour 11 minutes
    Distance:
    307 miles

    Questions we hear the most

    The average flight time from Chicago (Midway) to Cleveland is 1 hour 11 minutes.
    There are 85 weekly flights from Chicago (Midway) to Cleveland on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Cleveland 3 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Cleveland 3 times per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Cleveland with Southwest, check out our Low Fare Calendar.
    You can rent a car at Hopkins International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Cleveland—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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