WebHow Much Does it Cost To Fly From Midway Intl. (MDW)? The cheapest prices found with in the last 7 days for return flights were $48 and $24 for one-way flights to for the period specified. Prices and availability are subject to change. Additional terms apply. WebSouthwest.com ®; Routes; Boston (BOS) to Chicago (MDW) Flights from Boston (BOS) to Chicago (MDW) 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 …
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