Best Places to Shop in Chicago

Chicago is one of the best cities in the United States for shopping. You get big city fashions at Midwest prices, meaning it’s the best of both worlds. If you’ve got a little extra cash now this is the perfect time to hit the shopping hot spots in Chicago as retailers are dropping prices to help boost their sales.

Magnificent Mile

The Magnificent Mile in Chicago is simply a shopper’s paradise. The region is about a mile long and stretches from Oak Street to the Chicago River on North Michigan Avenue and is literally filled with shopping options. Wear your most comfortable dress shoes because you’ll want to look amazing yet you’ll be putting in quite a few miles. The stores range from high end boutiques to The Gap filling in every imaginable space in between. Don’t limit your shopping to what is visible from the street as there are a ton of malls and stores tucked inside of the store fronts and hotels along the way. It’s almost impossible to shop all of the Magnificent Mile in one day so plan on only hitting the highlights or spending several days enjoying this shopper’s paradise.

Oak Street

Chicago’s Oak Street is just off the Magnificent Mile and is one of the toniest shopping spots in the Midwest. These upscale stores are not for the faint of heart or budget and require a strong constitution when it comes to looking at the price tags. But if you’re in the mood for some luxury accessories or top end designer clothing then Oak Street is the place to be. You’ll find clothing, shoes, jewelry, home furnishings, art, linens, music and much more to suit your shopping yen. If you’re visiting the area and this type of shopping is your target then you’ll probably want to stay at one of the high end hotels in the area and definitely checkout some of the city’s most acclaimed restaurants, which are all within walking distance. In fact, just to round out the luxury shopping experience, there are numerous high end spas in the Oak Street area to soothe those sore shopping muscles.

State Street

State Street shopping in Chicago is sometimes referred to as shopping the Loop, but most of the stores (the good ones anyway) are centered on State Street so you can focus your shopping in this area. State Street was Chicago’s original great shopping district with seven of the largest and most sought after department stores around. The luxury and competition were astounding back in the WWI era but things have changed and State Street’s opulence has given way to discount stores and fast food outlets. Which isn’t such a bad thing if you’re looking for some great deals.

Jewelers’ Row

Chicago’s Jewelers’ Row is worthy of a stop if you’re looking for some sparkly stones to take home. Most of the stores along this region service wholesalers but 5 S. Wabash Avenue lets regular people come in off the street and shop to their heart’s content. It’s a real experience as it’s sort of like a flea market for delightful gems.

River North

River North is the place to go if you’re looking for some interior design inspiration as it’s anchored by the Merchandise Mart, the world’s largest commercial building, which houses basically everything you could ever want or desire. But just outside the doors of the Merchandise Mart are more than a handful of high end home furnishing boutiques and antique stores. River North is also a haven for artists with its own little gallery district. There is an art season in this area and it officially begins on the first Friday after Labor Day. But if you’re headed to Chicago in late July or through the month of August you’ll also hit a pre-amble to the big art season.

Armitage Avenue

Armitage Avenue is an older part of town with historic looking homes and, more recently, wealthy young professionals. To cater to these up and comers with lots of cash retailers have opened up high end boutiques that have an eclectic sensibility. You’ll find specialty stores with one of a kind clothing, interior décor, jewelry, and lots of odds and ends. Even though the area generally caters to those with money, there’s a neighborhood vibe throughout that makes the number of discount and consignment shops seem oddly at home. Like the high end Oak Street, Armitage Avenue features a number of salons or stores catering to those who know how to pamper. It’s a great place to wind up a day of shopping, find those one of a kind items you never even knew you needed and then submerge yourself in a self-indulgent spa treatment.

Bucktown/Wicker Park

The Bucktown/Wicker Park area has recently become the trendy place to shop in Chicago. It’s an unusual neighborhood where the old meets the new and art and bohemian spirit come to rest. There are one of a kind items that are a bit pricey and then there are must have items that come with reasonable price tags. The variety of stores is unmatched and this is the place to shop if you’re looking for a gift for someone who has everything and needs nothing. Bucktown/Wicker Park offers crafty and unique goods so if you’re looking for run of the mill and big discounts then this isn’t the area for you, but if you want something special and will spend a little more for it then plan a stop here.

In addition to these shopping centers in Chicago the city is full of other shops and stores which contain basically everything you could ever want. If you want to avoid the downtown area and want to shop in a more familiar surrounding there are hundreds of malls in the greater Chicagoland area, simply take your pick and enjoy the shopping extravaganza Chicago has to offer, but your best bet for incredible shopping is really the downtown, Magnificent Mile area, it’s like no other shopping experience around.