$70 Find Cheap Southwest Flights from Chicago to New York

When to Book Flights with Southwest from Chicago to New York

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

  Generally, when trying to get a below average price for your ticket, try to book around 15 days before departure. For the cheapest possible price, our data suggests booking 85 days before departure.

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

  With an average price of $291 return, Southwest is not the cheapest airline to fly from Chicago to New York with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $132 on average.

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

  In the last 3 days, the lowest price for a flight with Southwest from Chicago to New York was $50 for a return flight and $29 for a one-way flight.

• Does Southwest fly direct to New York from Chicago?

  Yes, Southwest does offer direct flights for the route, with around 7 flights per week.

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

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

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

  The cheapest month for Southwest flights to New York from Chicago is generally September, where plane tickets cost $113 on average. If possible, try to avoid the most expensive months of December and July, where tickets cost $236 and $238 respectively.