Earn 40,000 points
to find your place in the sun.Learn more
Trade Motor City for the Windy City with Southwest Airlines®. Southwest® has flights from Detroit Metropolitan Wayne County Airport to Chicago Midway International Airport that’ll make booking your next getaway a cinch. Find your flight from Detroit to Chicago (Midway) and book with confidence, knowing you’ve got cheap, enjoyable travel on the horizon. Upcoming trip have flexible dates? Explore flight options with the Low Fare Calendar and find the cheapest flights you’ve got within your travel window. Want more savings? Explore Southwest Vacations® to see deals on flights, hotels, and rental cars packages.
What’re you waiting for? Find and book your flight from Detroit to Chicago (Midway) now!
Departing from: Detroit Metropolitan Wayne County Airport (DTW)
Arriving at: Chicago Midway International Airport (MDW)
When you deplane at Chicago Midway International Airport, you’re a short Orange Line ride away from the center of the city and access to 77 neighborhoods worth of fun. Rental cars and rideshares are available too, of course, but when you take the ‘L’, you have a chance to take in the unique views from the elevated train system. If views are what you’re after, summit the highest building in the Western hemisphere—Willis Tower (or Sears Tower, as locals still call it). From the famous Skydeck Chicago Ledge, daredevils can step out onto a glass floor 1,353 ft. above the hustle and bustle of the streets below. The views don’t stop there, though. Chicago has architecture tours (by boat or on foot), food tours, mafia-related tours, haunted building tours, and tours amongst the neighborhoods. See for yourself.
While you’re touring the diverse neighborhoods of the city of the big shoulders, don’t forget to eat! Restaurant Row isn’t the only place to find Michelin-starred meals, but hole-in-the-wall dives and local faves abound and deserve your attention. Maybe you’re after a slice of famous Chicago-style pizza—but don’t let anyone tell you deep dish isn’t the only game in town. In fact, there are two kinds of ooey-gooey, larger-than-life pizza styles: deep dish and stuffed. However, Chicago natives actually call thin-and-crispy “party cut” or “tavern style” pizza true Chicago-style pie.
Of course, there’s much more to do when you land in Chicago than eat and take tours: museums, Navy Pier, Botanic Gardens, Broadway in Chicago, standup and improv shows—there’s so much to choose from. No matter how you choose to spend your time, flying from Detroit to Chicago (Midway) with Southwest Airlines makes booking a breeze.
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.
At Southwest, we understand that a memorable trip from Detroit to Chicago (Midway) contains more than cheap fares from Detroit Metropolitan Wayne County Airport to Chicago Midway International Airport. That’s why Southwest travelers have access to other services and perks, from booking to boarding, that make for smooth travel and set the stage for fun. Find out more about the Southwest Experience, and book your Detroit to Chicago (Midway) flight.
It’s simple and fun to fly with Southwest, whether for business or pleasure, to any of our myriad locations. When you search for your flight from Detroit to Chicago (Midway), you’ll find low fares without hidden fees—that’s Transfarency.® Stay up to date on our deals by enrolling in the Click 'N Save® emails. Looking for tours, activities, and more hidden gems? Check out Southwest Airlines® Experiences and earn Rapid Rewards® points when you book.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.