$59 Find Cheap American Airlines Flights from Boston to Chicago

When to Book Flights with American Airlines from Boston to Chicago

• How far in advance should I book tickets for a flight with American Airlines from Boston to Chicago?

  Generally, when trying to get a below average price for your ticket, try to book around 8 days before departure. For the cheapest possible price, our data suggests booking 39 days before departure.

• Is American Airlines the cheapest airline to fly with from Boston to Chicago?

  With an average price of $260 return, American Airlines is not the cheapest airline to fly from Boston to Chicago with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $104 on average.

• What is the cheapest American Airlines flight from Boston to Chicago?

  In the last 3 days, the lowest price for a flight with American Airlines from Boston to Chicago was $97 for a return flight and $48 for a one-way flight.

• Does American Airlines fly direct to Chicago from Boston?

  Yes, American Airlines does offer direct flights for the route, with around 12 flights per week.

• What’s the cheapest day of the week to fly from Boston to Chicago with American Airlines?

  On average, the cheapest day of the week to fly from Boston to Chicago with American Airlines is Tuesday, when prices are around $52. The most expensive day is generally Thursday, where the average price is around $78.

• What’s the cheapest month to fly from Boston to Chicago with American Airlines?

  The cheapest month for American Airlines flights to Chicago from Boston is generally January, where plane tickets cost $101 on average. If possible, try to avoid the most expensive months of April and December, where tickets cost $183 and $183 respectively.