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Find low faresSouthwest® flights from Cincinnati to Chicago (Midway) from $72
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Low fares from Cincinnati to Chicago (Midway)
$
Cincinnati (CVG)to
Chicago (Midway) (MDW)
Depart: 05/02/2026
One-way
Choice
From
$72
Seen: 13 hrs ago
Cincinnati (CVG)to
Chicago (Midway) (MDW)
Depart: 05/02/2026
One-way
Basic
From
$82
Seen: 13 hrs ago
Cincinnati (CVG)to
Chicago (Midway) (MDW)
Depart: 02/28/2026
One-way
Choice
From
$96
Seen: 8 hrs ago
Cincinnati (CVG)to
Chicago (Midway) (MDW)
Depart: 03/11/2026
One-way
Basic
From
$96
Seen: 11 hrs ago
Cincinnati (CVG)to
Chicago (Midway) (MDW)
Depart: 03/25/2026
One-way
Basic
From
$96
Seen: 12 hrs ago
Cincinnati (CVG)to
Chicago (Midway) (MDW)
Depart: 03/24/2026
One-way
Basic
From
$96
Seen: 12 hrs ago
Explore flights from Cincinnati to Chicago (Midway)
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Flight Details
Departing from:
Cincinnati/Northern Kentucky Airport
Arriving at:
Chicago Midway International Airport
Average flight time:
1 hour 9 minutes
Distance:
249 miles
Route Information
39† Weekly flights
- 1‡ Nonstop flight per day Monday through Friday
- 2‡ Nonstop flights on Saturday
- 2‡ 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.
Explore Chicago (Midway)
Whether your first order of business when you deplane at Chicago Midway International Airport is to belly up to a bar for a Chicago Handshake, to order up a tavern style pizza, or to hit the streets for a walking tour, the City of the Big Shoulders is ready to say hello! Grab a rental car, call a rideshare, or hop on the Orange Line of the ‘L’ and start your Windy City adventure.
Chicago is a city of neighborhoods, boasting 77 officially designated neighborhood areas. You likely won’t have time to hit each and every one of them in one visit, but you can pass through many of them aboard the ‘L’; consider buying a CTA pass and going on an uncharted expedition. Some of the best eats in the city can be found miles away from Restaurant Row, so pick up that Michelin Guide and venture to Logan Square, Avondale, Pilsen, or Bronzeville.
Questions we hear the most
The average flight time from Cincinnati to Chicago (Midway) is 1 hour 9 minutes.
There are 39 weekly flights from Cincinnati to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Cincinnati to Chicago (Midway) once per day from Monday through Friday.
Yes, Southwest flies nonstop from Cincinnati to Chicago (Midway) 2 times per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Cincinnati 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 Cincinnati 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.