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

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Low fares from Cincinnati to Chicago (O'Hare)

$

Cincinnati (CVG)to

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

One-way

Basic

From
$79
Seen: 17 hrs ago

Cincinnati (CVG)to

Chicago (Midway) (MDW)
Depart: 11/05/2026

One-way

Basic

From
$103
Seen: 22 hrs ago

Cincinnati (CVG)to

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

One-way

Basic

From
$103
Seen: 20 hrs ago

Cincinnati (CVG)to

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

One-way

Basic

From
$103
Seen: 21 hrs ago

Cincinnati (CVG)to

Chicago (Midway) (MDW)
Depart: 09/16/2026

One-way

Basic

From
$103
Seen: 11 hrs ago

Cincinnati (CVG)to

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

One-way

Basic

From
$103
Seen: 1 hour ago

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Explore flights from Cincinnati to Chicago (O'Hare)

Aug 2026
From$103*
Seen: 1 hour ago
One Way/Basic
Sep 2026
From$79*
Seen: 17 hrs ago
One Way/Basic
Oct 2026
From$103*
Seen: 10 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $103
cmp-daily-histogram-bars-legend-max-price-aria-label $245
Displaying fares for August-2026
  • CVG–MDW, 08/05/2026: From $228
    05

    Wed

    AUG

  • CVG–MDW, 08/06/2026: From $245
    06

    Thu

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

    Fri

  • CVG–MDW, 08/08/2026: From $228
    08

    Sat

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

    Sun

  • CVG–MDW, 08/10/2026: From $245
    10

    Mon

  • CVG–MDW, 08/11/2026: From $228
    11

    Tue

  • CVG–MDW, 08/12/2026: From $228
    12

    Wed

  • CVG–MDW, 08/13/2026: From $245
    13

    Thu

  • CVG–MDW, 08/14/2026: From $245
    14

    Fri

  • CVG–MDW, 08/15/2026: From $228
    15

    Sat

  • CVG–MDW, 08/16/2026: From $245
    16

    Sun

  • CVG–MDW, 08/17/2026: From $245
    17

    Mon

  • CVG–MDW, 08/18/2026: From $212
    18

    Tue

  • CVG–MDW, 08/19/2026: From $212
    19

    Wed

  • CVG–MDW, 08/20/2026: From $212
    20

    Thu

  • CVG–MDW, 08/21/2026: From $212
    21

    Fri

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

    Sat

  • CVG–MDW: cmp-view-offers-disclaimer. Find Offers
    23

    Sun

  • CVG–MDW, 08/24/2026: From $212
    24

    Mon

  • CVG–MDW, 08/25/2026: From $103
    25

    Tue

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

    Wed

  • CVG–MDW, 08/27/2026: From $103
    27

    Thu

  • CVG–MDW, 08/28/2026: From $137
    28

    Fri

  • CVG–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Sat

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

    Sun

  • CVG–MDW, 08/31/2026: From $103
    31

    Mon

  • CVG–MDW, 09/01/2026: From $103
    01

    Tue

    SEP

  • CVG–MDW: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

  • CVG–MDW, 09/03/2026: From $103
    03

    Thu

  • CVG–MDW, 09/04/2026: From $137
    04

    Fri

    • Range$103-$245

    *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:
    Cincinnati/Northern Kentucky Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    264 miles

    Route Information

    9† 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 9 weekly flights from Cincinnati to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Cincinnati 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 Cincinnati 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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