Earn 40,000 points
to find your place in the sun.Learn more
Bid the Paris of America adieu for Chicagoland with Southwest Airlines®. Southwest® has flights from Cincinnati/Northern Kentucky International Airport to Chicago Midway International Airport that’ll make booking flights for your next visit simple. Find your flight from Cincinnati to Chicago (Midway) and pack your bags for cheap, enjoyable travel. If your upcoming trip has flexible dates, explore additional flight options with the Low Fare Calendar and find the cheapest flights you’ve got within your designated travel dates. Want more savings? Visit Southwest Vacations® to see deals on flights, hotels, and rental cars packages.
Find and book your flight from Cincinnati to Chicago (Midway) now!
Departing from: Cincinnati/Northern Kentucky International Airport (CVG)
Arriving at: Chicago Midway International Airport (MDW)
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.
One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.
Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest Pet Policy.
Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
At Southwest, we understand that a memorable trip from Cincinnati to Chicago (Midway) is made up of more than cheap plane tickets from Cincinnati/Northern Kentucky International Airport to Chicago Midway International Airport. That’s why Southwest travelers have access to other services and perks, from booking to boarding, that make for smooth travel and set the stage for fun. Find out more about the Southwest Experience, and book your Cincinnati to Chicago (Midway) flight.
It’s simple and fun to fly with Southwest, whether for business or pleasure, to any of our myriad locations. When you search for your flight from Cincinnati to Chicago (Midway), you’ll find low fares without hidden fees—that’s Transfarency.® Stay up to date on our deals by enrolling in the Click 'N Save® emails. Looking for tours, activities, and more hidden gems? Check out Southwest Airlines® Experiences and earn Rapid Rewards® points when you book.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.