2015 Chicago Holiday Guide: Downtown Chicago Shopping

While all the holiday lights, festivals, and various other seasonal events and activities help shape the holiday season in Chicago, few things relate more to this time of year than shopping. And given we’re lucky enough to live in one of the best shopping cities in the world, there’s certainly no shortage of options to find everybody on your gift-giving list the perfect present. But if you’re looking for some of the best places to begin all your holiday shopping, here are just a few of our favorite suggestions:

The Magnificent Mile


Easily Chicago’s most famous shopping district, if you can’t find a great gift on Michigan Avenue, chances are it doesn’t exist. From luxury retailers to some of the most recognizable brands in fashion, shopping options and opportunities along the Mag Mile are limitless.

Oak Street in the Gold Coast

If you’re looking for something special for that special someone, you won’t find a better assortment of luxury goods and products than what’s all along Oak Street. In fact, since 2008, Oak Street has been known as the “Midwest’s luxury shopping district” and when you factor in the area’s 20+ eateries and restaurants, it’s one of the best places to spend the day shopping in the heart of downtown Chicago.

Clybourn Corridor

Although lots of stores and outlets have been situated near the North & Clybourn intersection, the addition of NewCity has really transformed this part of Lincoln Park into the go-to location for shopping on the north side. A new movie theatre, Dick’s Sporting Goods, an Apple Store, the Container Store, Express, Gap, Victoria’s Secret, J Crew, Crate and Barrel, and World Market are only some of the noteworthy stores in the area.

Block 37

Acting as the only mall in Chicago’s Loop, if you live in the city’s primary business and financial district and are looking for an easy and convenient place to get all your holiday shopping done, there’s no better place to check out than Block 37. But given it’s also connected to the Blue and Red Line, it’s also easy to get to from just about anywhere else in town.