Oak Street, Chicago

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.

Want to visit this sight? Check out these Self-Guided Walking Tours in Chicago. Alternatively, you can download the mobile app "GPSmyCity: Walks in 1K+ Cities" from Apple App Store or Google Play Store. The app turns your mobile device to a personal tour guide and it works offline, so no data plan is needed when traveling abroad.

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Oak Street on Map

Sight Name: Oak Street
Sight Location: Chicago, USA (See walking tours in Chicago)
Sight Type: Park/Outdoor
Guide(s) Containing This Sight:

Walking Tours in Chicago, Illinois

Create Your Own Walk in Chicago

Create Your Own Walk in Chicago

Creating your own self-guided walk in Chicago is easy and fun. Choose the city attractions that you want to see and a walk route map will be created just for you. You can even set your hotel as the start point of the walk.
The Magnificent Mile Walking Tour

The Magnificent Mile Walking Tour

The stretch of Michigan Avenue from the Chicago River to Lake Shore Drive, otherwise known as the Magnificent Mile, is regarded as one of the world’s great avenues – or Chicago’s version of Fifth Avenue. Take this self-guided walk to explore its whole stretch and surrounding area, featuring a wide selection of amazing stores/malls, world-known museums, restaurants and spectacular...  view more

Tour Duration: 3 Hour(s)
Travel Distance: 3.2 Km or 2 Miles
Chicago Chinatown Walking Tour

Chicago Chinatown Walking Tour

Tucked away just south of the Loop, the Chinatown of Chicago was established in 1912 and is considered one of the best examples of American Chinatown. While it may be one of Chicago’s smallest neighborhoods geographically, it is big on character, colors, sights, sounds, and flavors. Here, you’ll find a wide range of unique boutiques, specialty shops, religious sights, authentic Chinese...  view more

Tour Duration: 1 Hour(s)
Travel Distance: 1.7 Km or 1.1 Miles
Loop District Architecture Walking Tour

Loop District Architecture Walking Tour

Chicago features an outstanding architectural legacy, having long been connected with some of architecture's most important names: Frank Lloyd Wright, Louis Sullivan, Mies van der Rohe, Holabird & Root, and others. The multi-layered Loop District, in particular, offers an extensive number of Chicago’s famous architectural “must-sees” – from modern skyscrapers to historic buildings...  view more

Tour Duration: 3 Hour(s)
Travel Distance: 4.6 Km or 2.9 Miles
Chicago Navy Pier Walking Tour

Chicago Navy Pier Walking Tour

Additional to scenic views of the lake, the boats, and the city skyline, the Navy Pier offers a variety of attractions on the waterfront – for kids as well as adults – that draw nearly ten million people annually, making this Chicago's most visited spot. Yes, some may see it as a “tourist trap”, but it is worth the time and money to spend some time here, so take this self-guided walk...  view more

Tour Duration: 1 Hour(s)
Travel Distance: 1.0 Km or 0.6 Miles
Chicago Old Town Walking Tour

Chicago Old Town Walking Tour

Settled in 1850 by German immigrants, Chicago’s Old Town neighborhood is a popular destination for locals and visitors who cater to the entertainment venues, restaurants, pubs, coffee shops and boutiques – all of which have turned an area once referred to as the “Cabbage Patch” into an attraction that rivals Navy Pier, Wrigley Field and the Magnificent Mile.

Start your Old Town walking...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 2.6 Km or 1.6 Miles
Chicago Introduction Walking Tour

Chicago Introduction Walking Tour

Sitting on the shore of Lake Michigan in the U.S. State of Illinois, Chicago has had many nicknames throughout its history, including the Windy City, Chi-Town, Second City, and the City of the Big Shoulders referring to the numerous towers and high-risers that punctuate its skyline.

Prior to the Europeans, the area of today's Chicago was successively inhabited by various Native American...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 3.5 Km or 2.2 Miles

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