- Shopping the Town: Michigan Avenue is often touted as a shopper's paradise, thanks to its lineup of big-name designer boutiques and multilevel high-end shopping malls. But that's all stuff you can find in any other big city. For more distinctive items, head to Chicago's residential districts, where trendy independent clothing boutiques sit next to eclectic home design stores filled with one-of-a-kind treasures. The home decor shops along Armitage Avenue cater to stylish young families with plenty of spending money, while Wicker Park and Bucktown attract edgy fashionistas with a range of funky clothing shops. Southport Avenue (near Wrigley Field) and West Division Street (south of Wicker Park) are the newest cool shopping meccas — with no nametag-wearing conventioneers in sight.
- Soaking up Sun at Wrigley Field: It's a Chicago tradition to play hooky for an afternoon, sit in the bleachers at this historic baseball park, and watch the Cubbies try to hit 'em onto Waveland Avenue. Note that the Cubs sell out almost every game; your best bet is to buy tickets for a weekday afternoon (although you'll often find season ticket holders selling seats at face value in front of Wrigley right before a game). Even if you can't get in, you can still soak in the atmosphere at one of the neighborhood's many watering holes.
- Playing in the Sand: If you're staying at a downtown hotel, you can hit the sands of Chicago's urban beaches almost as quickly as your elevator gets you to the lobby. Oak Street Beach (at Michigan Ave. and Lake Shore Dr.) is mostly for posing. North Avenue Beach, a little farther north along the lakefront path, is home to weekend volleyball games, family beach outings, and a whole lot of eye candy. You probably won't do any swimming (even in the middle of summer, the water's frigid), but either beach makes a great place to hang out with a picnic and a book on a warm afternoon.
- Raising a Glass (or a Coffee Cup): Chicago has its share of trendy lounges that serve overpriced specialty martinis, but the heart of the city's nightlife remains the neighborhood taverns. These are the places you can soak in a convivial atmosphere without attitude or self-consciously flashy decor, but also have a conversation without being drowned out by the hoots and hollers of drunken frat boys (although there are plenty of bars catering to that particular demographic). Favorite local hangouts include Miller's Pub in the Loop, and the Map Room in Bucktown. If you prefer to keep things nonalcoholic, grab coffee and dessert at the 3rd Coast on the Gold Coast or Uncommon Ground in Wrigleyville.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.