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Cheap Flights from Chicago to Boston $172.61

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Cheapest Flights from Chicago to Boston (MDW to BOS)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Chicago to Boston (MDW to BOS)

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.