Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from Washington, D.C. (Reagan National) to Chicago (Midway) now!
Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from Washington, D.C. (Reagan National) to Chicago (Midway) now!
Washington, D.C. (Reagan National), DC to Chicago (Midway), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 41 travel days available. Fares are updated hourly. Fares displayed on external channels may no longer be available at time of booking. To find the most updated fare, please visit Southwest.com.
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
We make bag-checking a breeze with our flexible baggage policy. Here’s how to make your journey even smoother:
Take advantage of inflight entertainment with free movies4, free live TV5, free texting6, and $8 inflight Internet7.
We also offer free sodas, coffee, and snacks8—learn more about the inflight food and beverage experience.
Have a change of travel plans? We offer free same-day standby for all fare types. This means that you can retain your current flight while listing for standby on an earlier flight. If a seat becomes available, it’s yours at no charge!
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
| Fare | Fly one-way from $96 (departing on 1/14)* |
|---|---|
| Departing from | Ronald Reagan Washington National Airport (DCA) |
| Arriving at | Chicago Midway International Airport (MDW) |
| Average flight time | 2 hours 8 minutes |
| Distance | 601 miles |
| 156† | Weekly flights |
|---|---|
| 5‡ | 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):
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 1/1/2025 and 1/31/2025. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 1/1/2025 and 1/31/2025.
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 41 travel days available. Fares are updated hourly. Fares displayed on external channels may no longer be available at time of booking. To find the most updated fare, please visit Southwest.com.
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.
1EarlyBird Check-In® pricing starts at $15 one-way, and is subject to availability. Pricing may vary based on the popularity and length of each (one-way) flight. Please see optional travel charges for more details.
2Upgraded boarding prices and benefits are per eligible segment. Flights must be within 24 hours of departure to be eligible for upgraded boarding.
3First and second checked bags. Weight and size limits apply.
4Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
5Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
6Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
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.
8Flights traveling 175 miles or less will have only water available. Complimentary snacks are served on flights over 175 miles. If you’re flying between Hawaii and the continental U.S., you’ll have even more snacks to choose from.
9Free same-day standby: You can list for same-day standby for an earlier flight via a Southwest Customer Service Agent at the airport or the Southwest app or mobile web. You must request to be added to the same-day standby list at least 10 minutes prior to the scheduled departure of your original flight or the no-show policy will apply. If using the app or mobile web, you must list your name 30 minutes ahead of scheduled departure. You will receive a message based on the contact preference selected during booking if you are cleared on the flight. Group bookings and Unaccompanied Minors are not eligible for same-day standby. You will be required to pay any government taxes and fees associated with these itinerary changes but refunds will be provided. Your original boarding position is not guaranteed on your standby flight. Southwest Business Customers booked through travel agencies may need to see a Southwest agent at the airport for a standby listing. See Southwest.com/standby for more details.