$59 Find Cheap American Airlines Flights from Chicago to Boston

When to Book Flights with American Airlines from Chicago to Boston

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

  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 58 days before departure.

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

  With an average price of $243 return, American Airlines is not the cheapest airline to fly from Chicago to Boston with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $94 on average.

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

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

• Does American Airlines fly direct to Boston from Chicago?

  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 Chicago to Boston with American Airlines?

  On average, the cheapest day of the week to fly from Chicago to Boston with American Airlines is Monday, when prices are around $58. The most expensive day is generally Wednesday, where the average price is around $88.

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

  The cheapest month for American Airlines flights to Boston from Chicago is generally January, where plane tickets cost $121 on average. If possible, try to avoid the most expensive months of May and April, where tickets cost $178 and $183 respectively.