If you need to get from the D.C./Baltimore area to Chicago, Southwest Airlines® has you covered. Southwest® flies directly from Baltimore/Washington International Thurgood Marshall Airport to Chicago Midway International Airport. Booking with Southwest is easy, no matter if you're flying for business or pleasure. Have some wiggle room in your travel dates? Explore your options on the Low Fare Calendar and see if there is a flight available at a nicer price. Don't forget to explore Southwest Vacations® to see package deals with flights, hotels, rental cars, and more.
Browse flights from Baltimore/Washington (BWI) to Chicago (Midway) and book your next trip!
Baltimore/Washington (BWI), MD to Chicago (Midway), IL
departing on 12/13
one-way starting at*$101
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 20 travel days available.
|Departing from||Baltimore/Washington International Thurgood Marshall Airport (BWI)|
|Arriving at||Chicago Midway International Airport (MDW)|
|Average flight time||2 hours 7 minutes|
|5‡||Nonstop flights per day Monday through Friday|
|4‡||Nonstop flights on Saturday|
|5‡||Nonstop flights on Sunday|
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 12/1/2022 and 12/31/2022. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 12/1/2022 and 12/31/2022.
Baltimore may be Charm City, but you'll see that Chicago is just as charming. When you fly in from the D.C./Baltimore Area, you'll deplane at Chicago Midway International Airport on the Southwest side of Chicago. Unlike the East Coast, where everything's exceptionally close together, the Midwest has a little more room to stretch. Thankfully, Midway is only a half-hour Orange Line ride on Chicago's venerable CTA public transit system away from downtown—or the Loop, as the locals call it, named for the elevated train ring around the area. Once there, the city stretches before you, easily accessible by bus, train, automobile, or even rental bike!
Hungry for a taste of local cuisine? Sample some of the best plates in the culinary world on a trip to Restaurant Row in the West Loop (just west of the Magnificent Mile—consider a reservation after a day of shopping). It's rumored that chicken vesuvio originates from here, but who's to say, really? Looking for a meal with fewer frills? Try a slice of Chicago-style pizza (deep dish, stuffed, or thin) or have a dragged-through-the-garden, Chicago-style hot dog—just don't ask for ketchup!
If you have time, consider taking in a show. From the symphony to stadium shows featuring world-famous acts to blues and jazz clubs once (and still) helmed by greats of the genre, there's an evening of music for everyone to enjoy on any given night in Chi-Town. Sports fans can root for one of the home teams, and those looking for laughs can visit one of the improv stomping grounds or check out a bar-room open mic.
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 Baltimore/Washington (BWI) to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Baltimore/Washington International Thurgood Marshall 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.
5Available only on WiFi-enabled aircraft. Limited-time offer. Where available.
6Internet access for $8 a day, per device. In order to provide the best experience, we block access to certain high-bandwidth applications, websites, and video conferencing services, including, but not limited to, Netflix, HBO Max, Zoom, and Microsoft Teams. In consideration of the public environment onboard, we also block potentially offensive online content.