Lots and lots of places are offering "Free hotspots", such as hotels for their guests. Within a 5 minute walk of where I work, I can hit 4 or 5 different hotspots that are wide open. When it isn't -18 outside, myself and a couple of co workers will have lunch on the grass at one such place and surf on my Vaio. A buddy and I have hit and used over 75 different unsecured APs. My location is a TINY area, I would think that a city would have thousands.
A couple of the places (homes) even have unsecured shares. So I would think that "Yes" it is that easy.....