Oak Street, Chicago

Next to Michigan Avenue lies the charming shopping enclave known as "Oak Street". While some may consider it an integral part of the Magnificent Mile, it's worth noting that neighboring streets like Rush and Walton don't quite make the official cut.

The Oak Street area, though compact in size, possesses the ability to outshine the Mile with its array of ultra-chic boutiques. Here, you'll encounter fashion havens such as Prada, Jimmy Choo, and Jil Sander, along with the slightly more accessible Bebe, Juicy Couture, and Mac. If you're flush with cash, it's an enjoyable destination for retail therapy, albeit with a somewhat more subdued atmosphere compared to the bustling Mile. Moreover, Oak Street is home to a number of opulent historic mansions dating back to the 1800s, a testament to Chicago's wealthiest denizens of yesteryear.

In contrast, Rush Street takes an oblique course from Chicago Avenue to Elm Street and is characterized by its array of bars, sidewalk cafés, and traditional steakhouses, all of which remain lively around the clock. While many of the establishments here cater to tourists and may come with slightly inflated price tags, there are a handful of exceptions, including the Original Pancake House – a quaint, old-school breakfast spot with abundant outdoor seating.

Just a single block north of Elm Street, Division Street is the epicenter of exuberant nightlife, attracting hordes of spirited college students and young professionals come weekend nights. In a curious twist, the addition of middle-aged men on the prowl has earned this area the nickname "the Viagra Triangle". Among the Division Street hotspots, Butch McGuire's reigns supreme, drawing in a lively crowd of singles in pursuit of a good time and exuding all the charm one might expect from a college fraternity house.