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!
Boston Logan, MA to Chicago (Midway), IL
departing on 2/11
one-way starting at*$52
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 45 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 Coronavirus Travel Information page for information about potential restrictions on air travel.
Average flight time: 2 hours 55 minutes
Departing from: Logan International Airport (BOS)
Arriving at: Chicago Midway International Airport (MDW)
Nonstop flightper day
Other popular flights from BostonView our interactive map
†Based on DOT published scheduled average flights Monday-Friday between 12/11/2020 and 2/28/2021, as of 12/11/2020.
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 free. 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® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
How long is the flight from Boston Logan to Chicago (Midway)?
The average flight time from Boston Logan to Chicago (Midway) is 2 hours 55 minutes.
How many Southwest flights from Boston Logan to Chicago (Midway) occur daily?
There are 8 flights daily from Boston Logan to Chicago (Midway) on Southwest Airlines.
Does Southwest fly nonstop from Boston Logan to Chicago (Midway)?
Southwest flies nonstop from Boston Logan to Chicago (Midway) once daily.
What day is it cheapest to fly from Boston Logan to Chicago (Midway)?
To find the cheapest day and time to fly Boston Logan to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
Can I rent a car at Chicago Midway International Airport?
You can rent a car at Chicago Midway International Airport—book yours with your flight.
Can I change my flight reservation for my flight from Boston Logan to Chicago (Midway)?
Yes! Flights from Boston Logan to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Where can I find the status of my flight from Boston Logan to Chicago (Midway)?
Check the status of your upcoming Southwest flight here.
Where can I find answers to other questions about flying from Boston Logan to Chicago (Midway) with Southwest?
Check out the Southwest Airlines® FAQs for answers about everything Southwest.