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Cheap Flights from Boston to Chicago $182.22

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Cheapest Flights from Boston to Chicago (BOS to MDW)

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

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

Question : If speed is all that matters, how can you get from BOS to MDW as quickly as possible?
Answer : Southwest Airlines currently holds the fastest travel time with two hours and 45 minutes. For example, you would arrive in Chicago at 5:15 PM CDT if you left Boston at 3:30 PM EDT. Remember, there is a time change of one hour.

Question : Looking for the cheapest flight over the next 30 days?
Answer : As of Mar 20th, the cheapest day to fly from Boston to Chicago is Apr 4th. Tickets are currently being sold for $164, which is 57% below the average price for this route.

Question : Is the price you found a good deal?
Answer : Ranging anywhere from $164 to $819, prices for BOS to MDW do fluctuate a lot more than the majority of routes in the United States. Remember, the sooner you book, the more you'll be able to save.

Question : What is the cheapest round-trip ticket you can get to Chicago?
Answer : Prices are hitting as high as $819 over the next three months when flying to MDW from BOS. Check out Delta Air Lines, as they have been booking customers at just $164.

Question : Which airline has been on schedule to Chicago Midway International Airport (MDW) from Logan International Airport (BOS) the most?
Answer : The current leader is Southwest Airlines with a 79% on-time rate. Life has too much to offer to spend it waiting in an airport, so check out Southwest Airlines to get in and out of airports as quickly as possible. If they are late for some reason though, the average delay is less than half an hour.

Question : How many days should you spend in Chicago?
Answer : The average time spent in Chicago by travelers from Boston is four days.

Question : Will you do what it takes to get the absolute lowest-cost flight?
Answer : For the month of April, the cheapest day to fly is Wednesday. Flexibility is paramount when booking travel plans in order to keep travel costs down.

Question : Which airline is struggling to get to Chicago on time?
Answer : Flight Options is late on 100% of flights from Logan International Airport (BOS) to Chicago Midway International Airport (MDW) at the moment. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.

Question : How often is the Logan International Airport (BOS) to Chicago Midway International Airport (MDW) route delayed?
Answer : Passengers are currently getting to their destination on schedule 76% of the time, which ranks in the top 50% of the world. If a flight is late, though, expect an average of 22 minutes added to your flight time.

Question : What's the likelihood of you being delayed on this route?
Answer : The best measurement of overall promptness combines both on-time percentage and total delay minutes. BOS to MDW currently has 3 stars out of 5, an average score at best.

Question : How many departure times from Logan International Airport (BOS) to Chicago Midway International Airport (MDW) are there on a daily basis?
Answer : Each day is different, but on average, you can expect to see three available departure times. You won't have as many options on this route as most other routes departing the United States.

Question : What day of the week has the most flight time options?
Answer : Saturday has the greatest variety of flight times for Boston to Chicago with three. With 5,738 different time options, Sunday provides the most options on average across all flights departing the United States.

Question : How long will the flight typically be from Logan International Airport (BOS) to Chicago Midway International Airport (MDW)?
Answer : When flying from BOS to MDW, it will take two hours and 51 minutes on average.