Southwest® flights from Chicago (Midway) to Cleveland from $59

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Low fares from Chicago (Midway) to Cleveland

$

Chicago (Midway) (MDW)to

Cleveland (CLE)
Depart: 09/21/2026

One-way

Basic

From
$59
Seen: 23 hrs ago

Chicago (Midway) (MDW)to

Cleveland (CLE)
Depart: 10/22/2026

One-way

Basic

From
$59
Seen: 20 hrs ago

Chicago (Midway) (MDW)to

Cleveland (CLE)
Depart: 10/03/2026

One-way

Basic

From
$59
Seen: 10 hrs ago

Chicago (Midway) (MDW)to

Cleveland (CLE)
Depart: 09/22/2026

One-way

Basic

From
$59
Seen: 9 hrs ago

Chicago (Midway) (MDW)to

Cleveland (CLE)
Depart: 10/29/2026

One-way

Basic

From
$59
Seen: 17 hrs ago

Chicago (Midway) (MDW)to

Cleveland (CLE)
Depart: 11/07/2026

One-way

Basic

From
$59
Seen: 3 hrs ago

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Explore flights from Chicago (Midway) to Cleveland

Aug 2026
From$238*
Seen: 15 hrs ago
One Way/Basic
Sep 2026
From$59*
Seen: 16 hrs ago
One Way/Basic
Oct 2026
From$59*
Seen: 7 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $59
cmp-daily-histogram-bars-legend-max-price-aria-label $277
Displaying fares for August-2026
  • MDW–CLE, 08/22/2026: From $238
    22

    Sat

    AUG

  • MDW–CLE, 08/23/2026: From $267
    23

    Sun

  • MDW–CLE, 08/24/2026: From $267
    24

    Mon

  • MDW–CLE, 08/25/2026: From $238
    25

    Tue

  • MDW–CLE, 08/26/2026: From $238
    26

    Wed

  • MDW–CLE, 08/27/2026: From $277
    27

    Thu

  • MDW–CLE, 08/28/2026: From $267
    28

    Fri

  • MDW–CLE, 08/29/2026: From $238
    29

    Sat

  • MDW–CLE, 08/30/2026: From $267
    30

    Sun

  • MDW–CLE, 08/31/2026: From $267
    31

    Mon

  • MDW–CLE, 09/01/2026: From $238
    01

    Tue

    SEP

  • MDW–CLE, 09/02/2026: From $238
    02

    Wed

  • MDW–CLE, 09/03/2026: From $267
    03

    Thu

  • MDW–CLE, 09/04/2026: From $225
    04

    Fri

  • MDW–CLE, 09/05/2026: From $191
    05

    Sat

  • MDW–CLE, 09/06/2026: From $191
    06

    Sun

  • MDW–CLE, 09/07/2026: From $225
    07

    Mon

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

    Tue

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

    Wed

  • MDW–CLE, 09/10/2026: From $191
    10

    Thu

  • MDW–CLE, 09/11/2026: From $76
    11

    Fri

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

    Sat

  • MDW–CLE, 09/13/2026: From $185
    13

    Sun

  • MDW–CLE, 09/14/2026: From $59
    14

    Mon

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

    Tue

  • MDW–CLE, 09/16/2026: From $59
    16

    Wed

  • MDW–CLE: cmp-view-offers-disclaimer. Find Offers
    17

    Thu

  • MDW–CLE, 09/18/2026: From $76
    18

    Fri

  • MDW–CLE, 09/19/2026: From $59
    19

    Sat

  • MDW–CLE, 09/20/2026: From $144
    20

    Sun

  • MDW–CLE, 09/21/2026: From $59
    21

    Mon

    • Range$59-$277

    *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

    Route Information

    85† Weekly flights
    • 3‡ Nonstop flights per day Monday through Friday
    • 3‡ Nonstop flights on Saturday
    • 3‡ Nonstop flights on Sunday

    † 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

    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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