Hemingway's is a great Yorkville spot, at moderate Parkdale-ish prices.
It attracts everyone from frat boys, to lawyers, to pro sports players and celebs, but has a great atmosphere on any given night. In the summer there will be a lineup on Friday and Saturdays. Service can be slow on these nights, so be patient.
I recommend the "Shotover". It's the second level, same level as the bathrooms, on the South side. The main patios get ram-jammed most nights, plus the 'Shotover' folk tend to be more chilled out.
They serve great pub food until 2am, which is a huge bonus. Check it out on a random evening with pals, you won't be disappointed.
Cheers.