Question : In the next four weeks, what day should you book your trip?
Answer : As of January 16th, the best day for booking to Boston (BOS) from Chicago (MDW) is February 2nd. Bookings have been made roughly 13% below the average price for this route.
Question : Which airline is least likely to get you to BOS on time?
Answer : Delta Air Lines flights from MDW to BOS are delayed 50% of the time. If you're on Delta Air Lines, be sure to sign up for the delay notifications to stay up to date with your flight's status.
Question : Is price more important than specific travel days for you?
Answer : For the month of February, the cheapest day to fly is Saturday. Flexibility is paramount when booking travel plans in order to keep costs down.
Question : How many days should you spend in Boston if you're flying in from Chicago?
Answer : Over the next two months, travelers from MDW to BOS are planning on staying for four days on average.
Question : Is there another local airport that can get you to Boston?
Answer : Chicago Midway International Airport is a terrific airport, but there is a lower cost option - O'Hare International Airport. It's just 16 miles away, and flights are 49% cheaper over the next few months.