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: 11/12/2026

One-way

Basic

From
$59
Seen: 14 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 10/17/2026

One-way

Basic

From
$59
Seen: 12 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 12/12/2026

One-way

Basic

From
$59
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 11/07/2026

One-way

Basic

From
$59
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 11/14/2026

One-way

Basic

From
$59
Seen: 21 hrs ago

Chicago-Midway (MDW)to

Cleveland (CLE)
Depart: 11/16/2026

One-way

Basic

From
$59
Seen: 23 hrs ago

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Explore flights from Chicago-Midway to Cleveland

Sep 2026
From$235*
Seen: 18 hrs ago
One Way/Basic
Oct 2026
From$59*
Seen: 10 hrs ago
One Way/Basic
Nov 2026
From$59*
Seen: 23 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $59
cmp-daily-histogram-bars-legend-max-price-aria-label $292
Displaying fares for September-2026
  • MDW–CLE, 09/11/2026: From $277
    11

    Fri

    SEP

  • MDW–CLE, 09/12/2026: From $248
    12

    Sat

  • MDW–CLE, 09/13/2026: From $277
    13

    Sun

  • MDW–CLE, 09/14/2026: From $277
    14

    Mon

  • MDW–CLE, 09/15/2026: From $248
    15

    Tue

  • MDW–CLE, 09/16/2026: From $277
    16

    Wed

  • MDW–CLE, 09/17/2026: From $277
    17

    Thu

  • MDW–CLE, 09/18/2026: From $277
    18

    Fri

  • MDW–CLE, 09/19/2026: From $248
    19

    Sat

  • MDW–CLE, 09/20/2026: From $277
    20

    Sun

  • MDW–CLE, 09/21/2026: From $292
    21

    Mon

  • MDW–CLE, 09/22/2026: From $248
    22

    Tue

  • MDW–CLE, 09/23/2026: From $235
    23

    Wed

  • MDW–CLE, 09/24/2026: From $235
    24

    Thu

  • MDW–CLE, 09/25/2026: From $235
    25

    Fri

  • MDW–CLE, 09/26/2026: From $235
    26

    Sat

  • MDW–CLE, 09/27/2026: From $235
    27

    Sun

  • MDW–CLE, 09/28/2026: From $235
    28

    Mon

  • MDW–CLE, 09/29/2026: From $235
    29

    Tue

  • MDW–CLE, 09/30/2026: From $235
    30

    Wed

  • MDW–CLE, 10/01/2026: From $59
    01

    Thu

    OCT

  • MDW–CLE, 10/02/2026: From $86
    02

    Fri

  • MDW–CLE, 10/03/2026: From $59
    03

    Sat

  • MDW–CLE, 10/04/2026: From $195
    04

    Sun

  • MDW–CLE, 10/05/2026: From $59
    05

    Mon

  • MDW–CLE, 10/06/2026: From $59
    06

    Tue

  • MDW–CLE: cmp-view-offers-disclaimer. Find Offers
    07

    Wed

  • MDW–CLE, 10/08/2026: From $59
    08

    Thu

  • MDW–CLE, 10/09/2026: From $86
    09

    Fri

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

    Sat

    • Range$59-$292

    *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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