City Cast

3 Questions With Cheap Flights Guru Scott Keyes

Sidney Madden
Sidney Madden
Posted on June 5
A headshot of a man

Going founder Scott Keyes. (Courtesy of Scott Keyes)

Scott Keyes has been finding cheap airfare since he booked a round-trip flight from New York City to Milan for $130 in 2013. He runs Going, formerly Scott’s Cheap Flights, and shared how Chicagoans can save on travel.

Why is Chicago a good place for cheap flights?

“If you were to base where you live entirely on cheap flights, you'd be between New York and Chicago. It's not the size of a city that determines how many cheap flights you might find, it's competition between airlines. So O'Hare being United and American hubs and a Frontier focus city as well as Southwest at Midway, you see a lot of cheap flights in and out of Chicago.”

How do you get a cheap flight?

“Generally speaking, there is no cheapest time to book flights. But there are cheapest days to take flights: Tuesday, Wednesday, and Saturday. Those tend to be cheaper because business travelers usually avoid them.”

“Your best odds of booking a cheap flight occur during a ‘Goldilocks window,’ not too early or too late. If you're traveling domestically, that’s about one to three months in advance of travel. Internationally, it's two to eight months in advance. But if you're traveling during peak travel periods — summer, Christmas, or New Year’s — add a couple months.”“Some of the best deals (round-trip on good airlines) out of Chicago in the last 12 months or pre-pandemic were:

  • U.S. Virgin Islands for $70
  • Tokyo for $202
  • Australia for $493”

Which has better deals: O’Hare or Midway? Which do you prefer?

“O'Hare tends to have more deals because there's not only a lot more flights but also more airlines. I’ll go out of my way to fly through O'Hare rather than any other connecting airport because of Tortas Frontera.”

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