As a Canadian, I've always wondered about this when I've visited the States. The transition from swipe cards to chip cards was fairly painless, from the consumer's point of view, up here.
I think what helped make it work is the prevalence of Interac. Before chip cards, you'd swipe your card, verify the amount, select an account, and enter your PIN. The only thing that changed with the chip was that you inserted your card instead of swiped.
When credit cards started getting chips, people were already familiar with the process and just needed to be issued a PIN by the credit card issuer.