It's been years since I've done the Chilly Hilly but I don't remember anything as difficult as Queen Anne on that ride. I think there was as steep, but not as long. Taylor is a bit less steep than QA though.

Here's GPS data with an elevation plot for the Chilly Hilly:

https://connect.garmin.com/modern/activity/72320363

I got 2,340 feet over 33 miles. You could rack up similar numbers with a loop down to Seward Park and a return via Beacon Hill.