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 enjoyable travel on the horizon. Upcoming trip have flexible dates? Explore flight options with the Low Fare Calendar and find the lowest fares on 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!
Best Airline in the U.S. and North America & Best Economy Class and Low Cost Airline in North America.
Detroit, MI to Chicago (Midway), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 36 travel days available.
During the ongoing COVID-19 pandemic, the availability, health and safety procedures, operations, and schedules for local attractions are changing constantly. Please contact attractions directly for hours of operation, potential temperature screenings, and other possible health and safety procedures and restrictions. Visit our COVID-19 Travel Information page for information about potential restrictions on air travel.
Departing from: Detroit Metropolitan Wayne County Airport (DTW)
Arriving at: Chicago Midway International Airport (MDW)
Other popular flights from Detroit
View our interactive mapWhen 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.
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 Detroit to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Detroit Metropolitan Wayne County 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. Looking for tours, activities, and more hidden gems to add to your Chicago (Midway) adventure? Explore getaways with Southwest®. 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.
To find the lowest fares by day and time to fly Detroit to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
You can rent a car at Chicago Midway International Airport—book yours with your flight.
Yes! Flights from Detroit to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® FAQs for answers about everything Southwest.
Discussion Forum and StoriesMobile Apps
