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Cheap Flights from Boston to Chicago $90.8

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Cheapest Flights from Boston to Chicago (BOS to ORD)

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 ORD)

Question : Best case scenario, how quickly can someone get from BOS to ORD?
Answer : If you're able to take the shortest direct flight (which is offered by United Airlines), you will be able to leave BOS at 9:00 AM EDT and get to ORD at 10:51 AM CDT (two hours and 51 minutes). Remember, there is a one-hour time change.

Question : Interested in traveling in the next 30 days and want to get the lowest fare?
Answer : Since low prices are preferred, look at Mar 25th. As of Mar 20th, it's showing the cheapest ticket sales at $107. That is 40% below the average price for this route, so you can spend that extra cash on an adventure in Chicago.

Question : How much should a trip from Boston (BOS) to Chicago (ORD) cost?
Answer : Ranging from $99 to $307, prices for BOS to ORD fluctuate less than most routes in the United States. The further out you book a route, the more likely you are to save.

Question : Who's offering the cheapest round-trip flight to O'Hare International Airport (ORD) over the coming months?
Answer : Prices are hitting as high as $307 over the next three months when flying to ORD from BOS. Check out American Airlines, as they have been booking customers at just $99.

Question : Is there a preferred airline for getting to O'Hare International Airport (ORD) on schedule?
Answer : Virgin America leads the way with a 100% on-time rate. Don't spend more time waiting in an airport than you have to and stick with Virgin America on this route. Hopefully they keep that perfect record alive.

Question : How long do most people stay in Chicago?
Answer : Of course you're not most people, but if you were, you'd stay roughly five days.

Question : If your plans are flexible, have you considered changing your departure day?
Answer : The lowest-cost day to fly in April is Tuesday. Flexibility is paramount when booking travel plans in order to keep travel costs down.

Question : Which airline can you expect delays with on this route?
Answer : NetJets Aviation is late on 100% of flights from Logan International Airport (BOS) to O'Hare International Airport (ORD) at the moment. If you’re on NetJets Aviation, be sure to sign up for the delay notifications to stay up to date with your flight’s status.

Question : How often are flights late from Logan International Airport (BOS) to O'Hare International Airport (ORD)?
Answer : This particular route gets passengers to O'Hare International Airport on time 75% of the time, which puts it in the 50th percentile worldwide. When there is a delay, it averages about half an hour.

Question : Is this route your best bet for getting to Chicago with minimal delays?
Answer : The best measurement of overall promptness combines both on-time percentage and total delay minutes. BOS to ORD currently has 3 stars out of 5, an average score at best.

Question : If you’re booking BOS to ORD, how many different choices of departure times do you have?
Answer : The number of flight times varies by day, but on average, BOS to ORD sees 16 different options. Compared to the average route departing the United States with five flight times, you'll have more choices than most.

Question : What day of the week has the most flight time options?
Answer : Monday has the greatest variety of flight times for Boston to Chicago with 19. Saturday currently offers the least amount of flight times with only 12 options.

Question : About how long is the flight from Boston to Chicago?
Answer : When flying from BOS to ORD, it will take two hours and 58 minutes on average.