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!
Boston Logan, MA to Chicago (Midway), IL
departing on 11/28
one-way starting at*$89
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 56 travel days available.
|Departing from||Logan International Airport (BOS)|
|Arriving at||Chicago Midway International Airport (MDW)|
|Average flight time||2 hours 38 minutes|
|4‡||Nonstop flights per day Monday through Friday|
|4‡||Nonstop flights on Saturday|
|5‡||Nonstop flights on Sunday|
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 10/1/2023 and 10/31/2023. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 10/1/2023 and 10/31/2023.
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.
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. 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.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
6Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
7Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.