I take pinball based trips once in a while. I think Chicago was my favorite place to go just to play, eat and drink.
Look at the line ups at Headquarters, they have a couple of locations and mostly freeplay. Also Logan's is an important place to check out.
Last time I was there, I spent 4 days bouncing between these spots and loved every minute of it.
Since you're in Canada though, Toronto is a hot spot right now. Cabin Fever, 3030, Junction City Music Hall, California Sandwiches are all great places to play and there's a ton of single or double machine locations that are easy to travel between.
I'm sure you've been here before and know how awesome the city is! Just get an AirBnB on the west side and you'll have access to some great neighborhoods.
Here's a pretty up to date map with info on machines:
https://www.google.com/maps/d/viewer?mid=1gsjvE3XqhL6Jo5-Nhr7KRlT0ugs&hl=en_US