$69 Find Cheap Southwest Flights from Chicago to Boston

When to Book Flights with Southwest from Chicago to Boston

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

  Generally, when trying to get a below average price for your ticket, try to book around 7 days before departure. For the cheapest possible price, our data suggests booking 84 days before departure.

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

  With an average price of $253 return, Southwest is not the cheapest airline to fly from Chicago to Boston with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $115 on average.

• What is the cheapest Southwest flight from Chicago to Boston?

  In the last 3 days, the lowest price for a flight with Southwest from Chicago to Boston was $116 for a return flight and $58 for a one-way flight.

• Does Southwest fly direct to Boston from Chicago?

  Yes, Southwest does offer direct flights for the route, with around 24 flights per week.

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

  On average, the cheapest day of the week to fly from Chicago to Boston with Southwest is Sunday, when prices are around $48. The most expensive day is generally Saturday, where the average price is around $68.

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

  The cheapest month for Southwest flights to Boston from Chicago is generally June, where plane tickets cost $108 on average. If possible, try to avoid the most expensive months of October and September, where tickets cost $184 and $218 respectively.