Though Booking is up more than 10% this year, other travel stocks are winning out, with Spirit Airlines, JetBlue and Expedia logging some of the largest returns.
"A lot of the travel names have basically moved sideways since March," O'Hara told CNBC's "Trading Nation" on Friday. "But Bookings is breaking out. ... If it holds its current levels, it would be a new weekly closing high and that's very powerful by our work."
O'Hara set a $2,750 to $2,800 target for Booking, roughly 11.5% and 13.5% above its Monday trading price near $2,460.
"We are buyers of Booking on the breakout," O'Hara said.
Booking shares fell nearly 1% by midday Monday.