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 12/08
one-way starting at*$49
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 45 travel days available.
Middle seats open through November 30
Full exchange of fresh, outdoor air every 2-3 minutes while inflight
Face coverings required
Average flight time: 1 hour 24 minutes
Departing from: Kansas City International Airport (MCI)
Arriving at: Chicago Midway International Airport (MDW)
Nonstop flightsper day
Other popular flights from Kansas CityView our interactive map
†Based on DOT published scheduled average flights Monday-Friday between 10/9/2020 and 12/31/2020, as of 10/9/2020.
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.
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
Taking a trip from Kansas City to Chicago (Midway) is as memorable as you make it, but you’ll remember booking the flight as a breeze when you get a great deal on a direct flight with Southwest. See how else we go the extra mile—learn about the Southwest® Experience.
Whether you’re traveling for work or play, alone or with the whole family, booking with Southwest is straightforward. Low fares. No hidden fees. That’s Transfarency®. Stay up to date with our latest flight deals: Enroll in our Click 'N Save® emails. Looking for tours, activities, and more hidden gems? Check out Southwest Airlines® Experiences and earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
How long is the flight from Kansas City to Chicago (Midway)?
The average flight time from Kansas City to Chicago (Midway) is 1 hour 24 minutes.
How many Southwest flights from Kansas City to Chicago (Midway) occur daily?
There are 13 flights daily from Kansas City to Chicago (Midway) on Southwest Airlines.
Does Southwest fly nonstop from Kansas City to Chicago (Midway)?
Southwest flies nonstop from Kansas City to Chicago (Midway) 3 times daily.
What day is it cheapest to fly from Kansas City to Chicago (Midway)?
To find the cheapest day and time to fly Kansas City to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
Can I rent a car at Chicago Midway International Airport?
You can rent a car at Chicago Midway International Airport—book yours with your flight.
Can I change my flight reservation for my flight from Kansas City to Chicago (Midway)?
Yes! Flights from Kansas City to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Where can I find the status of my flight from Kansas City to Chicago (Midway)?
Check the status of your upcoming Southwest flight here.
Where can I find answers to other questions about flying from Kansas City to Chicago (Midway) with Southwest?
Check out the Southwest Airlines® FAQs for answers about everything Southwest.