Take a break from Jazz Capital of the World and get down with some blues in the Windy City. Southwest Airlines® flies direct from Kansas City International Airport to Chicago Midway International Airport. Book your flight to Chicago (Midway) on Southwest® with confidence, knowing your travel will be both easy and enjoyable. Does your trip have flexible dates? Put your date range into the Low Fare Calendar and see our lowest fares inside your range. Explore Southwest Vacations® for deals on flights, hotels, rental cars, and more.
What’re you waiting for? Explore flights from Kansas City to Chicago (Midway) and book yours now!
Kansas City, MO to Chicago (Midway), IL
departing on 3/18
one-way starting at*$59
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 26 travel days available.
|Kansas City International Airport (MCI)
|Chicago Midway International Airport (MDW)
|Average flight time
|1 hour 22 minutes
|Nonstop flights per day Monday through Friday
|Nonstop flights on Saturday
|Nonstop flights on Sunday
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 3/1/2024 and 3/31/2024. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 3/1/2024 and 3/31/2024.
When you think of the City of the Big Shoulders, there’s a good chance you picture the iconic skyline. When you visit Chicago, you can take in the view by land or sea (or, more accurately, lake or river) with popular tours, or you can view the skyline from within it. The Chicago Skydeck Ledge lets you step four feet out from the building, placing you 1,353 feet above the busy streets of downtown Chicago. If your nerves don’t take your breath away, the view sure will.
There’s more to see in Chicago than the skyline, of course. Museum fans are in for a treat and should consider a trip to one of the several that the city boasts. The Art Institute, the Field Museum, the Museum of Contemporary Art, the American Writers Museum, and the Museum of Science and Industry are all conveniently located near the Loop (what locals call the city’s downtown); the Chicago History Museum is further north, but should not be missed for true lovers of the town. More interested in flora and fauna than man-made masterpieces? Chicago boasts the Shedd Aquarium and Lincoln Park Zoo inside city limits, Brookfield Zoo in the western suburbs, and the Chicago Botanic Gardens in the northern suburbs. The latter two are easily accessible via Metra train.
The real charm of the city, though, is visible in and amongst the neighborhoods. Chicago is a city of neighborhoods, comprised of 77 designated community areas. Hop on a CTA bus or ‘L’ train and get exploring. Find yourself in a corner bar and try a Chicago Handshake. Stumble upon a pizza joint and have yourself a slice (deep dish or thin crust, it’s up to you). Treat yourself to ethnically diverse food, cultural centers and celebrations, and landmarks dotted across the city. It’s all yours to explore after you deplane at Midway.
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.
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 Kansas City to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Kansas City 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. 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.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
6Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
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.