$69 Find Cheap Southwest Flights from New York to Chicago

When to Book Flights with Southwest from New York to Chicago

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

  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 60 days before departure.

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

  With an average price of $273 return, Southwest is not the cheapest airline to fly from New York to Chicago with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $199 on average.

• What is the cheapest Southwest flight from New York to Chicago?

  In the last 3 days, the lowest price for a flight with Southwest from New York to Chicago was $49 for a return flight and $34 for a one-way flight.

• Does Southwest fly direct to Chicago from New York?

  Yes, Southwest does offer direct flights for the route, with around 35 flights per week.

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

  On average, the cheapest day of the week to fly from New York to Chicago with Southwest is Monday, when prices are around $68. The most expensive day is generally Saturday, where the average price is around $84.

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

  The cheapest month for Southwest flights to Chicago from New York is generally September, where plane tickets cost $93 on average. If possible, try to avoid the most expensive months of July and April, where tickets cost $236 and $239 respectively.