It may be called the Second City, but Chicago never takes a backseat to anyone. Chicago has always been a leader in architecture, as evidenced by the towering structures lining The Loop and the Chicago River seen from the not-to-miss architectural boat tours. It has produced some of the best music, live theater and comedians (including Bill Murray, Tina Fey, Amy Poehler and Bernie Mac) to emerge in the last 20 years. Sure, the city has had a reputation as a tough thug, but she always shows off her natural beauty and clean streets. If you've never been here, or haven't been in a few years, you're in for a treat. The last decade has seen an explosion in the food scene, cultural attractions and some of the best music festivals during the summer (Lollapalooza and Pitchfork lead the pack). While you're here, take the L or hop on a Divvy bike to travel around the city. Hit the West Loop's Randolph Street and Fulton Market for some of the best restaurants, Wicker Park to hear live music and chill out on the patio at Big Star and out to Logan Square for cutting-edge cocktails, hipster boutiques and even more delicious dining. And if you're really up for an adventure, visit in February. If nothing else, the lines will be shorter.