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 enjoyable travel. If your upcoming trip has flexible dates, explore additional flight options with the Low Fare Calendar and find the lowest fares on 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!
Best Airline in the U.S. and North America & Best Economy Class and Low Cost Airline in North America.
Cincinnati, OH to Chicago (Midway), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 48 travel days available.
During the ongoing COVID-19 pandemic, the availability, health and safety procedures, operations, and schedules for local attractions are changing constantly. Please contact attractions directly for hours of operation, potential temperature screenings, and other possible health and safety procedures and restrictions. Visit our COVID-19 Travel Information page for information about potential restrictions on air travel.
Departing from: Cincinnati/Northern Kentucky International Airport (CVG)
Arriving at: Chicago Midway International Airport (MDW)
Other popular flights from Cincinnati
View our interactive mapWhether 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.
Chicago Midway International Airport is a quick 30-minute 'L' ride from downtown Chicago. Get going—adventure awaits.
At Southwest, we know it takes more than great deals on Chicago (Midway) airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Cincinnati to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Cincinnati/Northern Kentucky International Airport to Chicago Midway International Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Chicago (Midway), know that you won’t be surprised at checkout. Low fares and no hidden fees. That's Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? Sign up to receive email from us. Looking for tours, activities, and more hidden gems to add to your Chicago (Midway) adventure? Explore getaways with Southwest®. Book your flight today and know that you'll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
To find the cheapest 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 here.
Check out the Southwest Airlines® FAQs for answers about everything Southwest.
Discussion Forum and StoriesMobile Apps
