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!
Washington, D.C. (Reagan National), DC to Chicago (Midway), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 23 travel days available.
Departing from | Ronald Reagan Washington National Airport (DCA) |
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Arriving at | Chicago Midway International Airport (MDW) |
Average flight time | 2 hours 3 minutes |
Distance | 601 miles |
92† | Weekly flights |
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6‡ | Nonstop flights per day Monday through Friday |
4‡ | Nonstop flights on Saturday |
5‡ | Nonstop flights on Sunday |
Other popular flights from Washington, D.C. (Reagan National):
View our interactive map†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 4/1/2024 and 4/30/2024. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 4/1/2024 and 4/30/2024.
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.
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 Washington, D.C. (Reagan National) to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Ronald Reagan Washington National 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.