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

Promo Code

Low fares from Cincinnati to Chicago (O'Hare)

$

Cincinnati (CVG)to

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

One-way

Basic

From
$79
Seen: 22 hrs ago

Cincinnati (CVG)to

Chicago (Midway) (MDW)
Depart: 09/19/2026

One-way

Basic

From
$79
Seen: 22 hrs ago

Cincinnati (CVG)to

Chicago (Midway) (MDW)
Depart: 10/15/2026

One-way

Basic

From
$79
Seen: 9 hrs ago

Cincinnati (CVG)to

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

One-way

Basic

From
$79
Seen: 3 hrs ago

Cincinnati (CVG)to

Chicago (Midway) (MDW)
Depart: 10/26/2026

One-way

Basic

From
$79
Seen: 9 hrs ago

Cincinnati (CVG)to

Chicago (Midway) (MDW)
Depart: 10/05/2026

One-way

Basic

From
$79
Seen: 1 hour ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Cincinnati to Chicago (O'Hare)

Aug 2026
From$228*
Seen: 7 hrs ago
One Way/Basic
Sep 2026
From$79*
Seen: 19 hrs ago
One Way/Basic
Oct 2026
From$79*
Seen: 9 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $79
cmp-daily-histogram-bars-legend-max-price-aria-label $245
Displaying fares for August-2026
  • CVG–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Tue

    AUG

  • CVG–MDW, 08/26/2026: From $228
    26

    Wed

  • CVG–MDW, 08/27/2026: From $245
    27

    Thu

  • CVG–MDW, 08/28/2026: From $245
    28

    Fri

  • CVG–MDW, 08/29/2026: From $228
    29

    Sat

  • CVG–MDW, 08/30/2026: From $245
    30

    Sun

  • CVG–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Mon

  • CVG–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

  • CVG–MDW, 09/02/2026: From $228
    02

    Wed

  • CVG–MDW, 09/03/2026: From $245
    03

    Thu

  • CVG–MDW, 09/04/2026: From $245
    04

    Fri

  • CVG–MDW, 09/05/2026: From $175
    05

    Sat

  • CVG–MDW, 09/06/2026: From $175
    06

    Sun

  • CVG–MDW, 09/07/2026: From $212
    07

    Mon

  • CVG–MDW, 09/08/2026: From $212
    08

    Tue

  • CVG–MDW, 09/09/2026: From $175
    09

    Wed

  • CVG–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Thu

  • CVG–MDW, 09/11/2026: From $175
    11

    Fri

  • CVG–MDW, 09/12/2026: From $175
    12

    Sat

  • CVG–MDW, 09/13/2026: From $212
    13

    Sun

  • CVG–MDW, 09/14/2026: From $79
    14

    Mon

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

    Tue

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

    Wed

  • CVG–MDW, 09/17/2026: From $94
    17

    Thu

  • CVG–MDW, 09/18/2026: From $103
    18

    Fri

  • CVG–MDW, 09/19/2026: From $79
    19

    Sat

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

    Sun

  • CVG–MDW, 09/21/2026: From $79
    21

    Mon

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

    Tue

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

    Wed

  • CVG–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Thu

    • Range$79-$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.

    Explore Flights from Other Popular Origins

    Popular Flights from Cincinnati