Bust out of Beantown for a day, a weekend, or longer and visit the Windy City—Southwest Airlines® flies from Logan International Airport to Chicago Midway International Airport. The City on a Hill will be easy to bid adieu when you see the low prices on fares at Southwest®. Book with confidence, knowing that you’ll experience a straightforward process. If you’re flexible about your departures and arrivals, check out the Low Fare Calendar to discover our cheapest flights in your date range. Explore Southwest Vacations® for deals on flights, hotels, rental cars, and more to make the most of your trip.
Find your next flight from Boston Logan to Chicago (Midway)—book today!
Average Flight Time: 2 hours 45 minutes
Departing from: Logan International Airport (BOS)
Arriving at: Chicago Midway International Airport (MDW)
Trade in the T for the ‘L’—when you deplane at Midway, you’ll find yourself on the Southwest side of Chicago and a 30-minute ‘L’ train ride away from downtown (what Chicago calls “the Loop”). From there, you can reach the whole city by public transit—the ‘L’ or buses—and begin your adventure, heading in whatever direction you choose. Shopping and theatre fans will want to stick around the Loop and adjacent areas for the Magnificent Mile shopping options and the Downtown Theatre District attractions. Fine dining fans should hop on the Pink or Green Line and head to Restaurant Row in the West Loop, home to what is widely believed to be the best cheeseburger around, Michelin-starred plates, and street food favorites—something to please every palate in the party.
Chicago is a city of neighborhoods. The city is composed of 77 community areas, each with their own storied history and hidden gems. A great way to take it all in—or narrow down where to start—is to visit the Chicago History Museum (in the Old Town Triangle neighborhood on the Northside). Fans of walking tours can traverse Chi-Town by tracing the footsteps of notorious Mafioso Al Capone, or exploring the examples of Prairie School housing stock and the surviving examples of Frank Lloyd Wright’s work. Whether you find affinity with Cubs fans or Sox fans, there’s something for everyone in each side of the City of the Big Shoulders.
When you find great deals on flights from Boston Logan to Chicago (Midway), you can spend your time (and your money) focused on exploring your destination instead of fretting about travel.
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.
A memorable trip to Chicago (Midway) is made of more than scoring a great deal on a flight from Boston Logan to Midway. That’s why Southwest works to make everything from booking to boarding memorable. Learn more about what goes into the Southwest Experience and book your next flight from Boston Logan to Chicago (Midway).
Journeying to Chicago (Midway) on Southwest is simple, fun, and straightforward. So is flying to any of our other dozens of destinations, thanks to Transfarency®: low fares, no hidden fees. And, as always, bags fly free1. Stay up to date with our latest flight deals: Enroll in our Click 'N Save® emails. Looking for tours, activities, and more hidden gems? Check out Southwest Airlines® Experiences and earn Rapid Rewards® when you book.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.