$262 Find Cheap Southwest Flights from Chicago to Honolulu

When to Book Flights with Southwest from Chicago to Honolulu

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

  With an average price of $757 return, Southwest is not the cheapest airline to fly from Chicago to Honolulu with. Instead, for the lowest price, our data suggests flying with Delta, where a return flight costs $578 on average.

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

  In the last 3 days, the lowest price for a flight with Southwest from Chicago to Honolulu was $531 for a return flight and $266 for a one-way flight.

• Does Southwest fly direct to Honolulu from Chicago?

  No, Southwest does not fly the route directly.

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

  On average, the cheapest day of the week to fly from Chicago to Honolulu with Southwest is Tuesday, when prices are around $249. The most expensive day is generally Thursday, where the average price is around $347.

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

  The cheapest month for Southwest flights to Honolulu from Chicago is generally January, where plane tickets cost $227 on average. If possible, try to avoid the most expensive months of June and December, where tickets cost $446 and $476 respectively.