Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from Cincinnati to Chicago (Midway) now!
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Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from Cincinnati to Chicago (Midway) now!
Cincinnati, OH to Chicago (Midway), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 42 travel days available. Fares are updated hourly. Fares displayed on external channels may no longer be available at time of booking. To find the most updated fare, please visit Southwest.com.
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
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.
Have a change of travel plans? We offer free same-day standby for all fare types. This means that you can retain your current flight while listing for standby on an earlier flight. If a seat becomes available, it’s yours at no charge!
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
| Fare | Fly one-way from $106 (departing on 5/24)* |
|---|---|
| Departing from | Cincinnati/Northern Kentucky International Airport (CVG) |
| Arriving at | Chicago Midway International Airport (MDW) |
| Average flight time | 1 hour 10 minutes |
| Distance | 249 miles |
| 45† | Weekly flights |
|---|---|
| 1‡ | Nonstop flight per day Monday through Friday |
| 1 ‡ | Nonstop flight on Saturday |
| 1 ‡ | Nonstop flight on Sunday |
Other popular flights from Cincinnati:
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 5/1/2025 and 5/31/2025. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 5/1/2025 and 5/31/2025.
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.
If your preferred use of your belly is laughter, get ready for nightly opportunities for chuckles. Chicago is a world-famous comedy town thanks to the rich history of improv comedy, but you’ll also find standup (both professional and open mics) and sketch comedy every night of the week. If you prefer theater, there are local troupes as well as Broadway in Chicago shows—something for every kind of theatergoer.
No matter what you’re hungry for when you land in Chicago or how you choose to spend your time, flying from Cincinnati to Chicago (Midway) with Southwest Airlines makes the booking-to-boarding portion of your trip a breeze.
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.
4Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
5Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
6Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
7Internet 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.
8Flights 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.
9Free same-day standby: You can list for same-day standby for an earlier flight via a Southwest Customer Service Agent at the airport or the Southwest app or mobile web. You must request to be added to the same-day standby list at least 10 minutes prior to the scheduled departure of your original flight or the no-show policy will apply. If using the app or mobile web, you must list your name 30 minutes ahead of scheduled departure. You will receive a message based on the contact preference selected during booking if you are cleared on the flight. Group bookings and Unaccompanied Minors are not eligible for same-day standby. You will be required to pay any government taxes and fees associated with these itinerary changes but refunds will be provided. Your original boarding position is not guaranteed on your standby flight. Southwest Business Customers booked through travel agencies may need to see a Southwest agent at the airport for a standby listing. See Southwest.com/standby for more details.