Southwest® flights from Cleveland to Chicago (O'Hare)

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Low fares from Cleveland to Chicago (O'Hare)

$

Cleveland (CLE)to

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

One-way

Basic

From
$59
Seen: 23 hrs ago

Cleveland (CLE)to

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

One-way

Basic

From
$59
Seen: 21 hrs ago

Cleveland (CLE)to

Chicago (Midway) (MDW)
Depart: 10/19/2026

One-way

Basic

From
$59
Seen: 13 hrs ago

Cleveland (CLE)to

Chicago (Midway) (MDW)
Depart: 09/29/2026

One-way

Basic

From
$59
Seen: 18 hrs ago

Cleveland (CLE)to

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

One-way

Basic

From
$59
Seen: 16 hrs ago

Cleveland (CLE)to

Chicago (Midway) (MDW)
Depart: 09/24/2026

One-way

Basic

From
$59
Seen: 2 hrs ago

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Explore flights from Cleveland to Chicago (O'Hare)

Aug 2026
From$238*
Seen: 5 hrs ago
One Way/Basic
Sep 2026
From$59*
Seen: 21 hrs ago
One Way/Basic
Oct 2026
From$59*
Seen: 3 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $59
cmp-daily-histogram-bars-legend-max-price-aria-label $267
Displaying fares for August-2026
  • CLE–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Tue

    AUG

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

    Wed

  • CLE–MDW, 08/27/2026: From $267
    27

    Thu

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

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

    SEP

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

    Wed

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

    Thu

  • CLE–MDW, 09/04/2026: From $267
    04

    Fri

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

    Sat

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

    Sun

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

    Mon

  • CLE–MDW, 09/08/2026: From $225
    08

    Tue

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

    Wed

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

    Thu

  • CLE–MDW, 09/11/2026: From $191
    11

    Fri

  • CLE–MDW, 09/12/2026: From $191
    12

    Sat

  • CLE–MDW, 09/13/2026: From $225
    13

    Sun

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

    Mon

  • CLE–MDW, 09/15/2026: From $59
    15

    Tue

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

    Wed

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

    Thu

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

    Fri

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

    Sat

  • CLE–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Sun

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

    Mon

  • CLE–MDW, 09/22/2026: From $59
    22

    Tue

  • CLE–MDW, 09/23/2026: From $59
    23

    Wed

  • CLE–MDW, 09/24/2026: From $59
    24

    Thu

    • Range$59-$267

    *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:
    O'Hare International Airport
    Distance:
    316 miles

    Route Information

    14† Weekly flights

    † 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

    There are 14 weekly flights from Cleveland to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Cleveland to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Cleveland to Chicago (O'Hare)—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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