Spending Christmas in Chicago: Where to Stay, What to Eat, and What to Do

Chicago is one of the best cities in the United States, and this is never more obvious than at Christmas. During the holiday season, the midwestern city of Chicago comes alive. Festive decor, snow-filled streets, and plenty of holiday activities make it one of the best Christmas destinations. So, if you’re spending the most wonderful time of the year in Chi-Town, continue reading for a guide on where to stay, what to eat, and what to do over Christmas in Chicago.

Where to Stay

Image via: The Peninsula Chicago

There is no shortage of upscale hotels in Chicago. The problem is narrowing it down and booking a stay in the one that best suits your personal style. The Peninsula Chicago (pictured above), the Waldorf Astoria Chicago, and The Ritz-Carlton Chicago are all located along the famous Magnificent Mile and are unsurprisingly some of the most luxurious properties in the city. In addition to world-class service and lavish amenities, these resorts typically go all-out with their holiday decor. So, if you want to pass by a glittering Christmas tree with all the trimmings every time you walk through the lobby, then any one of these 5-star hotels will suit you well.

For something a little off the beaten path, consider the Kimpton Gray Hotel. This property is boutique in style with a contemporary-meets-art deco aesthetic, and is more centrally located in the Chicago Loop area, mere steps from Millennium Park.

What to Eat

Image via: Girl & The Goat

Chicago is known for its cuisine, which is why partaking in the city’s food scene is a must while visiting for the holidays. Start your day with coffee and a donut from Stan’s Donuts & Coffee (the millennial pink sign is sure to draw you in) before making your way to Xoco for lunch (expect authentic yet innovative Mexican dishes from American chef Rick Bayless).

For dinner, we recommend checking out the hip West Loop area. From Girl & The Goat’s (pictured above) new American fare to Avec Restaurant’s Mediterranean-inspired dishes or Bar Siena’s regional Italian cuisine, you’re sure to fall in love with this trendy Chicago neighbourhood.

Lastly, no trip to Chicago would be complete without deep dish pizza. Luckily, you can find this culinary staple on practically every street corner in the Windy City. Giordano’s and Lou Malnati’s are two local favourites.

What to Do

Image via: Christkindlmarket

Chicago is full of fun holiday activities for people of all ages. Ice skating on the ribbon at Maggie Daley Park or the circular rink at McCormick Tribune Plaza (with the metallic bean as your backdrop!) both make for an idyllic December afternoon. Post-skate, head on over to the nearby Art Institute of Chicago and peruse its special Christmastime exhibition, which features an 18th century Neapolitan Creche. This display features one of the most intricate nativity scenes in existence.

From there, Chicago’s Christkindlmarket (the city’s very own German-style Christmas market, pictured above) is mere minutes away by foot. Set in Daley Plaza, this seasonal attraction welcomes more than one million visitors each year. At the market, you’ll find food and drinks like spiced apple cider, decadent hot chocolate, traditional lebkuchen, and bratwurst sausages, as well as plenty of artisanal gift items, such as handmade ornaments and toys. Some of the vendors come all the way from Germany and Austria to participate in this annual tradition.

Lastly, no holiday trip to Chicago is complete without a shopping trip on the Magnificent Mile. Everything from standalone boutique stores to upscale malls like 900 North Michigan Shops is open throughout the holiday season, with the exception of Christmas Day.

Emily Southey
Emily Southey is a freelance writer from Vancouver. Currently based in Toronto, it was during her time studying History and English at McGill and University College London that she became interested in writing. When she's not working, you can typically find her in a museum, baking cupcakes, watching Disney musicals, or Instagramming her new favourite coffee spot.