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Cheap MDW to BOS Flights

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

Chicago

$112.60

Providence

$192.00

Cheap MDW to BOS Flights

Question : Is the price you found a good deal?
Answer : Flight prices are fluctuating more for this route than the majority of routes in the United States, as they're ranging from $149 to $900. The further out you book a route, the more likely you are to save.

Question : Which airline is struggling to get to Boston on time?
Answer : If you decide to book your flight with Delta Air Lines, keep an eye on your departure time. 50% of flights from Chicago Midway International Airport (MDW) to Logan International Airport (BOS) are delayed.

Question : How often is the Chicago Midway International Airport (MDW) to Logan International Airport (BOS) route delayed?
Answer : Flights from MDW to BOS are on time 71% of the time, ranking in the bottom 50% of the world. When there is a delay, it averages 31 minutes.

Question : If traveling from MDW to BOS, how long can you expect to be in the air?
Answer : When flying from MDW to BOS, it will take two hours and 12 minutes on average.

Question : Which airline has been on schedule to Logan International Airport (BOS) from Chicago Midway International Airport (MDW) the most?
Answer : Executive Express Aviation leads the way with a 100% on-time rate. Spend as little time in an airport as necessary by flying with Executive Express Aviation. Hopefully they keep that perfect record alive.

Question : What is the shortest flight from MDW to BOS?
Answer : Southwest Airlines can get you there in two hours and 10 minutes. For example, if you were to leave Chicago at 8:55 PM CST, you would arrive in Boston at 12:05 AM EST (remember, there is a one-hour time difference).

Question : If your plans are flexible, have you considered changing your departure day?
Answer : For the month of January, the cheapest day to fly is Monday. Being flexible with your travel days garners even more savings during booking.

Chicago to Boston Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Chicago to Boston will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Boston.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with MDW to BOS flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to BOS with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.