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

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Low fares from Cleveland to Chicago (Midway)

$

Cleveland (CLE)to

Chicago (Midway) (MDW)
Depart: 09/11/2026

One-way

Basic

From
$59
Seen: 7 minutes ago

Cleveland (CLE)to

Chicago (Midway) (MDW)
Depart: 09/26/2026

One-way

Basic

From
$76
Seen: 20 hrs ago

Cleveland (CLE)to

Chicago (Midway) (MDW)
Depart: 09/02/2026

One-way

Basic

From
$76
Seen: 20 hrs ago

Cleveland (CLE)to

Chicago (Midway) (MDW)
Depart: 08/24/2026

One-way

Basic

From
$76
Seen: 10 hrs ago

Cleveland (CLE)to

Chicago (Midway) (MDW)
Depart: 10/06/2026

One-way

Basic

From
$76
Seen: 12 hrs ago

Cleveland (CLE)to

Chicago (Midway) (MDW)
Depart: 10/07/2026

One-way

Basic

From
$76
Seen: 12 hrs ago

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Explore flights from Cleveland to Chicago (Midway)

Aug 2026
From$76*
Seen: 10 hrs ago
One Way/Basic
Sep 2026
From$59*
Seen: 7 minutes ago
One Way/Basic
Oct 2026
From$76*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $76
cmp-daily-histogram-bars-legend-max-price-aria-label $287
Displaying fares for August-2026
  • CLE–MDW, 08/01/2026: From $238
    01

    Sat

    AUG

  • CLE–MDW, 08/02/2026: From $267
    02

    Sun

  • CLE–MDW, 08/03/2026: From $287
    03

    Mon

  • CLE–MDW, 08/04/2026: From $238
    04

    Tue

  • CLE–MDW, 08/05/2026: From $273
    05

    Wed

  • CLE–MDW, 08/06/2026: From $267
    06

    Thu

  • CLE–MDW, 08/07/2026: From $267
    07

    Fri

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

    Sat

  • CLE–MDW, 08/09/2026: From $287
    09

    Sun

  • CLE–MDW, 08/10/2026: From $267
    10

    Mon

  • CLE–MDW, 08/11/2026: From $273
    11

    Tue

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

    Wed

  • CLE–MDW, 08/13/2026: From $267
    13

    Thu

  • CLE–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Fri

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

    Sat

  • CLE–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Sun

  • CLE–MDW, 08/17/2026: From $225
    17

    Mon

  • CLE–MDW, 08/18/2026: From $225
    18

    Tue

  • CLE–MDW, 08/19/2026: From $225
    19

    Wed

  • CLE–MDW, 08/20/2026: From $225
    20

    Thu

  • CLE–MDW, 08/21/2026: From $110
    21

    Fri

  • CLE–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Sat

  • CLE–MDW, 08/23/2026: From $185
    23

    Sun

  • CLE–MDW, 08/24/2026: From $76
    24

    Mon

  • CLE–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Tue

  • CLE–MDW, 08/26/2026: From $76
    26

    Wed

  • CLE–MDW: cmp-view-offers-disclaimer. Find Offers
    27

    Thu

  • CLE–MDW, 08/28/2026: From $110
    28

    Fri

  • CLE–MDW, 08/29/2026: From $76
    29

    Sat

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

    Sun

  • CLE–MDW, 08/31/2026: From $76
    31

    Mon

    • Range$76-$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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