Depending on what you're going for, you could take a trip down to Havre. It's fairly easily to do in a day from Calgary. It's about 2hrs from Medicine Hat (so about a 5hr trip from Calgary) and while quite small, has a brand new casino that's quite nice (and will exchange Cdn $$ at par up to $500/day), some decent shopping (big Wal-Mart, big K-Mart, shopping center) and is a quick trip to Great Falls if you want to head on thru. I got a really nice room there 2wks ago for $80 USD for the night (including a really good breakfast too).
Don't think I'd go for longer than a day or 2 tops, but it wasn't bad for what it was. Just a reminder - check your duty-free allowances before heading back across the border. I got tagged for $30 cuz I thought I was allowed more than I actually was.
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