Right now, I have to admit that I’m cheating on my hometown and having a love affair with Chicago.

There’s just something about Chitown that inspires adoration and devotion. The architecture is a stunning mix between vintage restoration and contemporary modernism, the food is fantastic, and there’s a sense of romantic history about the entire city — rather like New York City, but less crowded and polluted. And to me, Chicago is also synonamous with hockey, as the first Stanley Cup playoff series I can ever remember watching was between the Chicago Blackhawks and the Pittsburgh Penguins (yay!).

You’ve never been to Chicago? Go. Right now. Especially because you definitely don’t want to miss this year’s NHL Winter Classic - Red Wings vs Blackhawks - being held at Wrigley Field on New Year’s Day.

The 2009 NHL Winter Classic line is a tricky one to cap. Normally, you’d look at the matchup of up-and-comers on the Blackhawks (who are, once again and finally, possible Stanley Cup contenders) versus the veterans of the Red Wings (who are, obviously, the current Stanley Cup holders), and you’d automatically lean towards the boys of Motor City. But, given that two of the Red Wings’ key players - defenseman Nicklas Lidstrom and goaltender Chris Osgood - are day-to-day with injuries (Lidstrom may be back as early as tomorrow though), there may just be a chance for Chicago’s young guns yet.

Not to mention they’re a bunch of hot young hockey foxes.

(You can’t tell from that picture, but oh baby. Put ‘em up there next to the roster of Vancouver Canucks - MINUS Mats Sundin, thanks - for Alice’s holiday wish list.)

Still, if you’re a smart betting woman, you’ll know that hotness doesn’t necessarily win games — experience and skill does. And while the ‘Hawks are rising in those terms, the Red Wings have them licked when it comes to “big games” and the pressure that comes with it. I love the underdog here, but my overall sportsbook pick would be the Red Wings. Much as I’m still bitter that they beat my poor Pens in the playoffs last year…sighhh.