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 lowest available fares 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!
Best Airline in the U.S. and North America & Best Economy Class and Low Cost Airline in North America.
Boston Logan, MA to Chicago (Midway), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 83 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 | Logan International Airport (BOS) |
|---|---|
| Arriving at | Chicago Midway International Airport (MDW) |
| Average flight time | 2 hours 48 minutes |
| Distance | 861 miles |
| 79† | Weekly flights |
|---|---|
| 2‡ | Nonstop flights per day Monday through Friday |
| 3‡ | Nonstop flights on Saturday |
| 3‡ | Nonstop flights on Sunday |
Other popular flights from Boston Logan:
View our interactive map†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 10/1/2021 and 10/31/2021. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 10/1/2021 and 10/31/2021.
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.
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 Boston Logan to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Logan International 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.
The average flight time from Boston Logan to Chicago (Midway) is 2 hours 48 minutes.
There are 79 weekly flights from Boston Logan to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Boston Logan to Chicago (Midway) 2 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Boston Logan to Chicago (Midway) 3 times per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Boston Logan 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 Boston Logan 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
