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The Grid: 5 festive ways to spend the holidays in the Loop

The heart of Chicago’s downtown, the Loop, comes to mind when thinking of where people go to work, rather than live. But along with the expected hustle and bustle of living in the city’s hub, residents boast about easy commutes to work (many just walk a few blocks), access to lush green spaces, museums, shopping and entertainment. 

In my round-up for this holiday edition of “The Grid,” I’ve chosen to visit the Loop because it’s packed with special events just for the season that are perfect to be shared with loved ones. There’s less than a week to catch some of the seasonal favorites, but the rest are worth a visit year-round. Here’s my pick for the top 5: 

1. Christkindlmarket 

Chicagoans love their street festivals in the summer, but Christkindlmarket is the penultimate must-do festival during the holidays. 

Taking inspiration from the German festival originating in Nuremberg in 1545, Chicago’s version started in 1995 by “The German American Chamber of Commerce of the Midwest” to promote trade. There’s plenty to buy if you’re still looking for a gift — ornaments, scarves, textiles and German clocks and nutcrackers. 

There’s still time to get your souvenir mug filled with Glühwein (mulled wine of spices and fruit), chai or hot chocolate. A perfectly grilled bratwurst or schnitzel sandwich could easily lift your mood if you’re feeling harried or stressed out by your holiday to-do list. I’m partial to the stuffed pretzels and raclette (melty, gooey Alpine cheese that’s scraped onto a baguette) but then again, I’m all about carb-loading. 

It runs until Christmas Eve in Daley Plaza.

2. Macy’s Walnut Room 

The Walnut Room at Macy’s displays its spectacular Great Tree until Jan. 6. The 45-foot-tall tree, suspended by wires from the ceiling, is adorned with more than 2,000 ornaments and twinkles with more than 6,000 lights. If you’re entertaining out-of-town guests, there’s a buffet and princess fairies that grant wishes to children. Of course, there’s a visit to Santa in an elaborate North Pole house. And don’t forget about the animated State Street window displays that have been famous for over fifty years. 

The restaurant still serves “Mrs. Hering’s Chicken Pot Pie” in honor of the Marshall Field’s sales associate who shared her lunch with a tired shopper one day.  Mrs. Hering’s pies were a hit with hungry women shoppers who would otherwise have had to return home. (At the turn of the 19th century, it was considered unacceptable for a woman to dine in public unless escorted by a man.) The resulting tea room where women could relax and socialize resulted in more shopping too!

3. Chicago Athletic Association Hotel 

If you’re looking for an overload of holiday vibes and cheer, then head over to Happy’s on the ground floor of the Chicago Athletic Association Hotel. The decor includes a mock sleigh you can sit in and enjoy your speciality festive cocktail. They even have evening programs like sweater slipper making and chainstitch embroidery classes. The explosion of twinkling lights, trees and garlands can be enjoyed until Dec. 23. 

If you’re in the mood for a less festive vibe, there are plenty of other spots you can head to in the hotel. The Milk Room is an eight-seat micro-bar (utilized in Prohibition) that specializes in the rarest vintage spirits and elixirs. A reservation is required in order to book a seat. 

The Game Room’s bar is casual and has a small food menu with crowd favorites like wings and burgers. And as the name suggests, there are games — billiards, bocce, foosball and shuffleboard. For a sit-down meal you can head to the tucked away and elegant Cherry Circle Room.  

One of my favorite views in the city year-round is from the terrace at Cindy’s, the rooftop restaurant at the hotel. The views face Millennium Park, Cloudgate and the Art Institute. In the winter, the warmth from the fireplaces makes it a nice place to enjoy a cocktail. 

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4. Millennium Park 

I love to visit Millennium Park during the holidays. I know it’s crowded, but once you’re there it’s magical. If you ice skate, you have two options in the park — the Skating Ribbon at Maggie Daley Park and the McCormick Tribune Plaza Ice Rink. Skating is free, but if you don’t own skates there is a rental fee. There are free ice skating lessons on the weekend. 

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5. Chicago Architecture Center

The Chicago Architecture Center has a “Holiday Lights, City Lights” bus tour. Currently, the “Building Tall” exhibit is on the second floor. The supersized scale models of famous skyscrapers from Chicago and around the world give a sense of just how tall skyscrapers have become over history and in comparison to familiar Chicago landmarks. By the way, the world’s first skyscraper was built in Chicago. The Home Insurance Building was built in 1885, topping off at ten stories. In 1890, two more stories were added but in 1931, it was torn down to make way for a new building. 

My favorite exhibit is the “Chicago City Model Experience” which features more than 4,000 model buildings on a map of the city’s grid. An interactive touch screen illuminates a series of light shows that highlight different points of history, like the Great Chicago Fire.  

One more thing…

If you’re with a crowd and you can’t decide where to eat, I’d recommend Revival Food Hall. It’s a fast-casual food dining hall but its thoughtful, chic design makes it worthy of an evening out. The best part of the concept is it supports “all-local dining” spotlighting over a dozen of the city’s acclaimed and beloved neighborhood restaurants. With choices from sushi to barbecue and favorites like tacos and pizza, everyone in your entourage will be satisfied. There’s a sleek, modern bar as well and it’s a comfortable place to sit a spell.

Here's how you can follow Ji Suk Yi on social media

Here’s how you can follow Ji Suk Yi on social media

We’re proud to welcome Baird & Warner as presenting sponsor of “The Grid.” Leading our video adventure is Sun-Times program host, Ji Suk Yi.

This new Sun-Times video series showcases the best of Chicago’s neighborhoods by turning a spotlight on the people, places and things that make our city one-of-a-kind. Look for a new video episode each Wednesday on the Chicago Sun-Times website. We hope you will watch, read and share all of “The Grid” stories!

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