W Irving Park/N Ashland Ave parking on a Saturday afternoon/evening?

Well, the farther you're willing to walk, the more likely it is you'll easily find a spot. So if you have the mindset of heading out instead of circling, you'll definitely find a spot within 5 minutes. You just might have a couple block walk. Although it is also entirely possible that you could find parking in an instant. That area is nowhere nearly as crazy as other neighborhoods in terms of parking availability.