In Winnipeg, MB, Canada it's somewhat easy to find free wifi around the city. It's not always there - as it is the benevolent stores offering it up as a perk. But I will say it's certainly put free 802.11b/g on the map and given it a badly needed voice.

When traveling for work (usually to Alberta), people have said I can expense off wifi time at the airport, but I prefer to go without. While it would be nice to get the full techie experience while traveling, the prices are just too opportunistic. I watched all the free wifi at airports disappear as the major players put their pieces into place. If I'm going to pay for internet access on a regular basis, I want it everywhere I go.

As for hotels... In Canada and the Northern USA they almost always have free wireless internet with varying - usually crippled - degrees of quality. Even some small motels in rural Saskatchewan have free access!
The Fairfield Inn-Mariott in Grand Forks is the best I've seen to date where they actually offered real IPs on request through their management software! The speed was comparable to a home connection no less, I complimented them at the front desk in person as these kinds of things need to happen more often.

I'm hoping that the auction of wireless bandwidth in Canada recently will open things up a bit more - but I'm not holding my breath. The only people interested in - and capable of!! - investing in communications infrastructure in Canada are greedy and progress averse albatrosses.

That's half the reason why I prefer to ride on the coattails of small businesses' goodwill and obtain a practical and unrestricted device like the N810. It represents a badly needed correction in wireless innovation: away from the monopolies and dishonest business practices wireless providers are so clearly guilty of.
As a bonus, if the business has something I can buy at the time, I'll almost always do so or at least do so a majority of the time. They have a proactive and positive interest in what they do (Espresso Junction @ the Forks in Winnipeg, this goes out to you!).

This has somewhat inspired me to see if my DDWRT flashed Linksys router is capable of joining a free wifi ring.