Why Oak Street Should Be On Every Chicago Visitor’s List

There’s only one terrible thing about visiting Chicago…

The city has so much to offer that it can be truly challenging to figure out what to do and see if you only have a limited time to spend here.

As dyed-in-the-wool Chicago lovers, we could write a whole book on what visitors should do, but one thing that all of us at the Oak Street Council agree on is that this part of the city is not to be missed.

The History

The Gold Coast is one of Chicago’s oldest and most historically notable neighborhoods in the whole city and, in fact, much of the area is even protected as a historical landmark since it was added to the National Register of Historic Places in 1980. The Gold Coast’s architecture and place in history is what makes it so special.

In addition to being home to landmarks like the original Playboy mansion and the Drake Hotel, it’s interesting to note that this neighborhood was home to the city’s richest residents in the early 20th century. A stroll around the area will leave visitors in awe of the stunning homes that the Second City’s original elite built for themselves here.

The Shopping

Perhaps what Oak Street is most famous for is the fact that it is the undisputed epicenter of upscale shopping in the city. There’s no shortage of great shopping opportunities on the nearby Magnificent Mile, but Oak Street offers something special. Unlike Michigan Avenue, Oak Street is quiet, intimate and feels exclusive.

That’s no surprise considering that it’s home to designer boutiques like Hermès, Jimmy Choo, Prada, Giorgio Armani and many, many more. After all, Oak Street is known as Chicago’s Rodeo Drive. Visitors love the fact that they can walk into any of the gorgeous shops and know they’ll get the very best in personal customer care while they browse everything from luxurious leather handbags to bespoke Italian suits – it’s a special experience you don’t find just anywhere.

The Dining

There’s no question that Chicago is one of the preeminent food cities in the world, so we don’t blame you if you have a hard time narrowing down your choices when you’re here. There are only so many meals in a day, right? But just make sure that your itinerary includes at least one meal at one of the many acclaimed fine dining establishments on Oak Street.

If you want a classic Chicago steakhouse experience, there’s nothing better than Gibson’s or Del Frisco’s; for delicioso Italian fare, there’s Carmine’s and Spiaggia; and if you like contemporary American cuisine, LUXBAR and Tavern on Rush are sure to impress. And those are just a few of the many great restaurants in the area to choose from.

We might be a little biased but we sincerely believe that no visit to Chicago is complete without a day spent on Oak Street, where history, style and luxury come together to offer a unique experience you won ‘t soon forget.

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