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: 12/07/2026

One-way

Basic

From
$59
Seen: 22 hrs ago

Cleveland (CLE)to

Chicago-Midway (MDW)
Depart: 10/01/2026

One-way

Basic

From
$59
Seen: 22 hrs ago

Cleveland (CLE)to

Chicago-Midway (MDW)
Depart: 10/22/2026

One-way

Basic

From
$59
Seen: 18 hrs ago

Cleveland (CLE)to

Chicago-Midway (MDW)
Depart: 10/29/2026

One-way

Basic

From
$59
Seen: 19 hrs ago

Cleveland (CLE)to

Chicago-Midway (MDW)
Depart: 12/10/2026

One-way

Basic

From
$59
Seen: 15 hrs ago

Cleveland (CLE)to

Chicago-Midway (MDW)
Depart: 10/20/2026

One-way

Basic

From
$59
Seen: 12 hrs ago

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Explore flights from Cleveland to Chicago-Midway

Sep 2026
From$235*
Seen: 23 hrs ago
One Way/Basic
Oct 2026
From$59*
Seen: 22 hrs ago
One Way/Basic
Nov 2026
From$59*
Seen: 19 hrs 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 September-2026
  • CLE–MDW, 09/12/2026: From $258
    12

    Sat

    SEP

  • CLE–MDW, 09/13/2026: From $287
    13

    Sun

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

    Mon

  • CLE–MDW, 09/15/2026: From $258
    15

    Tue

  • CLE–MDW, 09/16/2026: From $258
    16

    Wed

  • CLE–MDW, 09/17/2026: From $287
    17

    Thu

  • CLE–MDW, 09/18/2026: From $287
    18

    Fri

  • CLE–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Sat

  • CLE–MDW, 09/20/2026: From $287
    20

    Sun

  • CLE–MDW: cmp-view-offers-disclaimer. Find Offers
    21

    Mon

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

    Tue

  • CLE–MDW, 09/23/2026: From $258
    23

    Wed

  • CLE–MDW, 09/24/2026: From $287
    24

    Thu

  • CLE–MDW, 09/25/2026: From $245
    25

    Fri

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

    Sat

  • CLE–MDW, 09/27/2026: From $245
    27

    Sun

  • CLE–MDW, 09/28/2026: From $245
    28

    Mon

  • CLE–MDW, 09/29/2026: From $245
    29

    Tue

  • CLE–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Wed

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

    Thu

    OCT

  • CLE–MDW, 10/02/2026: From $120
    02

    Fri

  • CLE–MDW, 10/03/2026: From $120
    03

    Sat

  • CLE–MDW, 10/04/2026: From $205
    04

    Sun

  • CLE–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Mon

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

    Tue

  • CLE–MDW, 10/07/2026: From $120
    07

    Wed

  • CLE–MDW, 10/08/2026: From $120
    08

    Thu

  • CLE–MDW, 10/09/2026: From $120
    09

    Fri

  • CLE–MDW, 10/10/2026: From $120
    10

    Sat

  • CLE–MDW, 10/11/2026: From $164
    11

    Sun

    • 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:
    Hopkins International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    1 hour 16 minutes
    Distance:
    307 miles

    Route Information

    89† 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 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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