Southwest® flights from Cincinnati to Chicago (Midway) from $79
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Low fares from Cincinnati to Chicago (Midway)
$
Cincinnati (CVG)to
Chicago (Midway) (MDW)
Depart: 01/08/2026
One-way
Basic
From
$79
Seen: 9 minutes ago
Cincinnati (CVG)to
Chicago (Midway) (MDW)
Depart: 02/24/2026
One-way
Basic
From
$82
Seen: 3 hrs ago
Cincinnati (CVG)to
Chicago (Midway) (MDW)
Depart: 01/07/2026
One-way
Basic
From
$92
Seen: 9 minutes ago
Cincinnati (CVG)to
Chicago (Midway) (MDW)
Depart: 01/08/2026
One-way
Choice
From
$94
Seen: 9 minutes ago
Cincinnati (CVG)to
Chicago (Midway) (MDW)
Depart: 01/06/2026
One-way
Basic
From
$96
Seen: 8 minutes ago
Cincinnati (CVG)to
Chicago (Midway) (MDW)
Depart: 02/24/2026
One-way
Choice
From
$101
Seen: 3 hrs ago
Explore flights from Cincinnati to Chicago (Midway)
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Travel tips for your next Southwest flight
How to board the plane earlier on open seating flights departing on or before January 26, 2026:
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
- Purchase EarlyBird Check-In®1 for automatic check-in and a better boarding position.
- Purchase Upgraded Boarding2 to get an A1-A15 boarding position (depending on availability).
- Purchase a Business Select® fare or upgrade to Business Select to get a guaranteed A1-A15 boarding position.
Enjoy movies, sips, and snacks during your flight.
Take advantage of inflight entertainment with free movies4, free live TV5, free texting6, and $8 inflight Internet7.
We also offer free sodas, coffee, and snacks8—learn more about the inflight food and beverage experience.
Make the most of our Rapid Rewards® Program.
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
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.
Explore Flights from Other Popular Origins
Popular Flights from Cincinnati
1EarlyBird Check-In® pricing starts at $15 one-way, and is subject to availability. Pricing may vary based on the popularity and length of each (one-way) flight. Please see optional travel charges for more details.
2Upgraded boarding prices and benefits are per eligible segment. Flights must be within 24 hours of departure to be eligible for upgraded boarding.
3Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
4Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
5Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
6Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.
7Flights traveling 175 miles or less will have only water available. Complimentary snacks are served on flights over 175 miles. If you’re flying between Hawaii and the continental U.S., you’ll have even more snacks to choose from.