When the Windy City calls you away from the Capital Region, Southwest Airlines® has you covered with direct flights from Ronald Reagan Washington National Airport to Chicago Midway International Airport. Book your Southwest® flight confidently, knowing your travel will be easy and enjoyable. If your trip to Chicago (Midway) has flexible dates, put your date range into the Low Fare Calendar and see what savings we have in store for you. Build a whole vacation package with Southwest Vacations®—find flight and hotel deals, rental car savings, and more.
Explore Washington, D.C. (Reagan National) to Chicago (Midway) flights and book yours now!
Average Flight Time: 1 hour 55 minutes
Departing from: Ronald Reagan Washington National Airport (DCA)
Arriving at: Chicago Midway International Airport (MDW)
Discover what keeps the City of the Big Shoulders standing tall. Take the iconic skyline, for example: The Willis Tower (or the Sears Tower, as Chicagoland lifers still call it) is the tallest building in the Western hemisphere—and you can venture over the edge of it when you visit the Chicago Skydeck Ledge! Fancy peering straight down from 1,353 feet above the streets of downtown Chicago? Maybe you’d prefer to view the iconic architecture of the city from safely at sea level. There are walking tours and boat tours (both boozy and family friendly) from the Chicago River and on Lake Michigan.
There’s much more to see in the Windy City than what the Loop (what Chicagoans call downtown) has to offer. Hop aboard an ‘L’ train (part elevated rail, part subway, all adventure) or bus, and let the CTA take you to the far reaches of the city. Chicago is built of 77 community areas, each of which has something for you to explore. From national institutions to neighborhood haunts, the less commercial areas of the city are just as entertaining as the Mag Mile or Restaurant Row—maybe even more so. Don’t forget to treat yourself to a slice of Chicago-style pizza (locals will tell you it’s actually the thin-crust kind, not the deep dish or stuffed).
Flying Southwest from Washington, D.C. (Reagan National) to Chicago (Midway) with low fares will leave you room to spend more on enjoying Chicago. Maximize savings by exploring our deals on rental cars, hotels, and more—even entire vacation packages. Whether you’re in Chicago for a short time on the way to elsewhere or are staying indefinitely, your trip there will go smoothly with Southwest.
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.
Planning a memorable trip from Washington, D.C. (Reagan National) to Chicago (Midway) takes more than scoring a great deal on a direct flight from Ronald Reagan Washington National Airport to Chicago Midway International Airport. But wait—there’s more! See what sets us apart and learn about the Southwest Travel Experience.
Whether you’re flying from Washington, D.C. (Reagan National) to Chicago (Midway) or any of our other dozens of destinations, booking with Southwest Airlines® is straightforward. You’ll encounter no hidden fees and enjoy low fares. That’s Transfarency®. Stay up to date with our latest flight deals by enrolling in our Click 'N Save® emails. Want extra help planning your next trip? Explore the Southwest Travel Guide.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.