A group of men in wigs and high heels slap each other’s asses outside of Roscoe’s Tavern on North Halsted. If you’re a woman, you’re feeling slighted that the queens look more beautiful than you on your best day. With a vibrant rainbow flag waving in the background, you see local drag persona Britney Shears saunter past in short shorts and mile-high heels. She does her signature bleach-blonde hair flip and it’s on. Dinner’s at Taverna 750 where the ridiculously cute bartender shakes your martini to the beat of Ricky Martin’s “Livin’ La Vida Loca.” Later, you can’t wait to hit up Sidetrack and gawk at shirtless men while worshipping Beyoncé’s latest single.
Things have changed — hanging ducks adorn window fronts, vendors are peddling live frogs, and unfamiliar dialects are flooding your senses. Won Kow serves up a wicked Mai Tai and tops it off with a tropical drink umbrella. Souvenir shops sell ginseng, teapots, Hello Kitty stuffed animals, and gold-pawed waving money cats. You can’t seem to resist steaming hot dim sum from MingHin Cuisine. Since you parked under the train tracks and got validated (thanks MingHin!) you spend your last few bucks on a fruit tart from Feida Bakery.
A tough-looking grandma swears loudly at punk kids hanging around her front porch and tells them to “git-to-git outta here!” The sound of bucket drummers fills the air and you decide to duck in for a Pabst Blue Ribbon at Bernice’s Tavern before the Sox game. A ticket scalper in baggy shorts hawks tickets to passersby while a Mexican woman sells homemade tamales out of her Coleman cooler street side. After celebrating a Sox win, you line up for an all-beef Chicago dog at 35th Street Red Hots.
A woman dressed all in Prada elbows past you, arms full of bags from Armani, Hermés, Louboutin, and Barney’s New York. She nearly gets hit by a taxi crossing Oak Street, because not only is she hiding behind giant Ralph Lauren sunglasses, but she’s gabbling away on her cell phone about how much of a dick her ex-husband is. Businessmen devour prime rib and lobster tail dinners al fresco at Gibson’s Bar and Steakhouse, while service industry folk (i.e. the tired-looking bartender with ratty hair and bags under her eyes) slink into divey Dublin Bar and Grill to rest their aching feet — and psyches — over copious pints of Guinness.
On Clark Street you’re weaving in between well-to-do, clean-cut yuppie couples and their double-wide strollers…strollers that nearly put your car to shame. A pierced and tattooed college kid whizzes past on his fixed gear and nearly knocks over runners from DePaul’s cross-country club. Their bright futures flash before your eyes. You consider dinner at Alinea, then remember the two-month waiting list… Churros outside the chimpanzee house at the free zoo will have to do. Later, you answer the calling to booze and blues at Kingston Mines ‘til 4 am.
You ride the escalators down from LaSalle Street Station with the men and women who’ll spend the day shouting over one another on the trade room floor. Walking to Grant Park along with hundreds, no thousands, of other people decked out in daisy dukes and tie-dyed shirts can only mean one thing — Lollapalooza. Men in tuxedos and women in black dresses wield instrument cases across Michigan Avenue to make it to warm-up for the Chicago Symphony Orchestra. You hop on the El…and quickly wish you’d never bothered — Chicago’s urban confines are most definitely best explored on foot. 
