chicago christmas

Whether you prefer vintage finds or outlet discounts, boutique-style gems or unique home items, everyone has their own holiday shopping habits, and many involve steering clear of downtown shopping crowds. And whereas Chicago has plenty of shopping hotspots on its famed Magnificent Mile, here are some of our favourite – and less crazy at this time of year! – shopping experiences in the Windy City.

Neighbourhood Boutiques 

A Little Bit Of This, Lakeview:  A Little Bit Of This is Chicago's only full service monogram boutique, located in the Southport Corridor of Lakeview. Open since 2004, A Little Bit Of This is a great resource for all things personalized - gifts for babies, children or teachers.

CarefulPeach Boutique, Oak Park: Looking for a smart and stylish home item for a friend? CarefulPeach specializes in unique household items that are crafted with old world charm. These rare and uncommon gems are as beautiful as they are functional - elegant crystal tableware, luxurious European linens, handcrafted jewellery and French luxury soaps.

Sir and Madame, Ukranian Village: Created by the stylish, dynamic husband-and-wife duo Brian and Autumn Merritt, Sir and Madame is a nostalgic men's and women's clothing boutique, perfect for that ever-difficult gift for your significant other. This boutique offers a fresh perspective for fashion-savvy urbanites.

Outlet Malls

Chicago Premium Outlets is a bargain hunter heaven at this time of the year. Boasting brands such as Ann Taylor, Armani, Banana Republic, Calvin Klein, Coach, Gap Outlet, J Crew Factory, Nike, Polo Ralph Lauren and Sony. This outlet mall is well worth the 40-minute drive west of the city.

Fashion Outlets of Chicago brings together more than 120 of the world's most relevant retail brands, and is anchored by Bloomingdale's outlet store, Last Call by Neiman Marcus, Forever 21 and Saks Fifth Avenue OFF 5th. Located just a quick drive away in Rosemont, you'll find unparalleled designer deals that are sure to make anyone on your holiday shopping list happy.

Vintage Shopping

Seek Vintage, West Town:  Seek is West Town's old-school darling. The shop is adorable, the staff is incredibly sweet and the selection is downright impressive. It’s the perfect place to find a gift for that friend with admirable, quirky style.

Vintage Underground, Wicker Park/Bucktown: Browsing through the piles of heavy costume jewels at this store feels a lot like rummaging through your rich grandma's basement. Know someone who just moved into a new home? The shop also stocks a handful of more budget-friendly home furnishings.

Knee Deep, Pilsen: Upon walking into Knee Deep, a vintage fanatic will be in awe at the jaw-dropping items hanging from the neatly packed racks. Owners Trent and Carlos pride themselves on being very meticulous and cautious about each item they sell.