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: 11/03/2026

One-way

Basic

From
$59
Seen: 9 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 12/24/2026

One-way

Basic

From
$59
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 12/16/2026

One-way

Basic

From
$59
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 12/09/2026

One-way

Basic

From
$59
Seen: 4 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 12/29/2026

One-way

Basic

From
$59
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 10/27/2026

One-way

Basic

From
$59
Seen: 3 hrs ago

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Explore flights from Chicago-Midway to Cleveland

Oct 2026
From$59*
Seen: 3 hrs ago
One Way/Basic
Nov 2026
From$59*
Seen: 18 hrs ago
One Way/Basic
Dec 2026
From$59*
Seen: 1 hour ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $59
cmp-daily-histogram-bars-legend-max-price-aria-label $287
Displaying fares for October-2026
  • MDW–CLE, 10/02/2026: From $287
    02

    Fri

    OCT

  • MDW–CLE, 10/03/2026: From $258
    03

    Sat

  • MDW–CLE, 10/04/2026: From $287
    04

    Sun

  • MDW–CLE, 10/05/2026: From $287
    05

    Mon

  • MDW–CLE, 10/06/2026: From $258
    06

    Tue

  • MDW–CLE, 10/07/2026: From $258
    07

    Wed

  • MDW–CLE, 10/08/2026: From $287
    08

    Thu

  • MDW–CLE, 10/09/2026: From $287
    09

    Fri

  • MDW–CLE, 10/10/2026: From $258
    10

    Sat

  • MDW–CLE, 10/11/2026: From $287
    11

    Sun

  • MDW–CLE, 10/12/2026: From $287
    12

    Mon

  • MDW–CLE, 10/13/2026: From $258
    13

    Tue

  • MDW–CLE, 10/14/2026: From $258
    14

    Wed

  • MDW–CLE, 10/15/2026: From $245
    15

    Thu

  • MDW–CLE, 10/16/2026: From $245
    16

    Fri

  • MDW–CLE, 10/17/2026: From $245
    17

    Sat

  • MDW–CLE, 10/18/2026: From $245
    18

    Sun

  • MDW–CLE, 10/19/2026: From $245
    19

    Mon

  • MDW–CLE, 10/20/2026: From $245
    20

    Tue

  • MDW–CLE, 10/21/2026: From $245
    21

    Wed

  • MDW–CLE, 10/22/2026: From $59
    22

    Thu

  • MDW–CLE, 10/23/2026: From $86
    23

    Fri

  • MDW–CLE, 10/24/2026: From $59
    24

    Sat

  • MDW–CLE, 10/25/2026: From $205
    25

    Sun

  • MDW–CLE: cmp-view-offers-disclaimer. Find Offers
    26

    Mon

  • MDW–CLE, 10/27/2026: From $59
    27

    Tue

  • MDW–CLE, 10/28/2026: From $59
    28

    Wed

  • MDW–CLE, 10/29/2026: From $59
    29

    Thu

  • MDW–CLE, 10/30/2026: From $86
    30

    Fri

  • MDW–CLE, 10/31/2026: From $59
    31

    Sat

  • MDW–CLE, 11/01/2026: From $164
    01

    Sun

    NOV

    • Range$59-$287

    *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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