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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 Airport/Thurgood Marshall 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!
Average flight time: 2 hours 2 minutes
Departing from: Baltimore/Washington International Airport/Thurgood Marshall (BWI)
Arriving at: Chicago Midway International Airport (MDW)
Nonstop flightsper day
Flights before noon
Flights after 6pm
Other popular flights from Baltimore/Washington
|Milwaukee (MKE)||Grand Rapids (GRR)|
|Indianapolis (IND)||Detroit (DTW)|
*Based on DOT published scheduled average Monday-Friday departures between 6/29/2020 and 1/4/2021, as of 6/29/2020.
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.
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
We know that a fun, memorable trip is made of more than a cheap flight from the Capitol Region to Chicago (Midway), which is why Southwest offers more. Learn more about our services and perks, from booking to boarding, and the Southwest Travel Experience while you book your Baltimore/Washington (BWI) to Chicago (Midway) flight.
No matter which of our dozens of destinations you're headed to, booking with Southwest is straightforward. There are no hidden fees tacked onto our low fares at checkout—that's our Transfarency® promise. Enroll in our Click 'N Save® emails to stay up to date on our latest and greatest deals. 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.