5 Kickass… Streets for Holiday Shopping in Chicago

The holiday season — believe it or not — is upon us. And, like it or not, that means lots and lots of shopping. If you’re anything like me, and classify the city as your #1 true love, that probably means you inevitably hate shopping malls. Shopping malls tend to have the same effect on me as the flu — feverish, overwhelming, and dizzying. There’s a more pleasant way to get your holiday shopping in Chicago done — one that doesn’t involve shiny floors and escalators. Here are our 5 kickass ways to get through the holiday shopping season — sans malls! Hint: they’re our favorite shopping streets in the city…

State Street/Mag Mile | Downtown | Check it out

While this may be two streets, if you’re looking for holiday cheer and pretty much every chain store in the country, you’ll find it here. Gap, Banana Republic, Macy’s, Bloomingdales, H&M, Crate & Barrel… we could go on for hours. The Magnificent Mile will undoubtably get you in the holiday spirit with twinkling lights strung on every tree and Christmas music floating out onto the sidewalks from every store. Once you’ve walked the mile, head a few blocks west to State Street. We recommend starting at Lake and State, where Macy’s boats elaborate holiday displays in their store windows. They’re nothing compared to the holiday windows of Marshall Fields, but they still have children and adults alike stopping to look.

Halsted & Armitage | Lincoln Park | Check it out

Ok, two streets again… but most good shopping districts will have you walking for more than just a couple blocks. As the yuppie capital of Chicago, Lincoln Park is retail heaven. Boutiques and high-end stores line the streets of Halsted and Armitage. So, if you’re looking for good shopping here’s our road map. Start at Halsted and Belden and head south down Halsted, meandering in and out of the shops until you hit Armitage. Hang a right and walk west until you think there just can’t be anymore fabulous stores in a 10-block radius. Make sure you check out Art Effect, Lori’s Shoes, and Vosges Haut Chocolat shop — they’re among our favorite places for creative gifts. You might just get all your holiday shopping in Chicago done in one swoop!

Southport Corridor | Lakeview | Check it out

Shopping on the Southport Corridor is almost a relaxing experience. Almost. (Remember, you’re holiday shopping in Chicago. Nothing about that can be completely zen.) Take the Brown Line to the Southport stop and head north when you exit the train. Various boutiques and shops line both sides of the street, so be sure not to miss any stops along the way. Visit Candyality if you want your candy fortune read, and maybe pick up some treats to fill your friend’s stockings. Try M2 for Men for the hard-to-shop-for boyfriend, husband, or brother. If your legs (or wallet) are feeling tired, take a break and grab a bite at one of the many coffee shops or restaurants on the block.

Damen/Milwaukee | Wicker Park/Bucktown | Check it out

For a slightly more alternative shopping trip, start at Damen and Armitage in Bucktown and head south to Milwaukee in Wicker Park, for shopping that ranges from Marc Jacobs and BCBG to Reckless Records and a handful of vintage and thrift stores. The Bucktown and Wicker Park shopping area of Chicago is a quickly growing community that has become increasingly more affluent in recent years. The stores are a reflection of the diverse and trendy residents that are the heart of these West Side villages. Whether you’re looking for local Chicago designers, high-end retailers, or vintage boutiques, there’s something for everyone in this eclectic shopping district.

Lincoln Avenue | Lincoln Square | Check it out

This German-influenced section of Chicago is especially picturesque around the holidays. I could wander Merz Apothecary perusing different products for hours, so you’re sure to find an intriguing gift or two there. Cooking classes from the Chopping Block make great gifts for your foodie friends, and Timeless Toys will have everything for the kiddos. This neighborhood can make you feel like you’re hours from downtown, so if all of those holiday tourists are making your head spin, this is a great place to go without leaving city limits. For more on Lincoln Square, check out our video series “Under the L –The Western Brown Line.”

Tessa McLean

About Tessa McLean

There is just something about that feeling when you have been away — maybe for a weekend, a month, 6 months — and you’re driving into Chicago and that first glimpse of the city skyline appears. It just always makes me smile.

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