24 hours in Chicago for December

Published on December 23, 2022

Chicago shines for the holidays! Pack a warm coat, hat, gloves and scarf and come play in our winter wonderland! If warm boots and clothes aren’t part of your regular wardrobe, make a scarf a souvenir. You can find inexpensive cold weather gear everywhere, even Walgreens! 

There’s so much to do! Check out my complete list of holiday activities before the end of the year. Here a few personal must-dos: 

  1. Kick off your day with some activity to get the blood moving. Many locals grow up skating at a local rink or playing hockey so if you’re like me, you own your own skates, so you can skate for free at several locations. Many enjoy skating in circles under The Bean at Millennium Park or the new rink at Wrigley Field’s Gallagher Way which also extends inside Wrigley Field in a new experience called Winterland. My personal favorite is the cloverleaf at Maggie Daley Park’s Ice-Skating Ribbon, flanked by the skyscrapers of Lakeshore East. When finished, get your land legs going again with a tour around Millennium Park with the Discover Millennium Park tour on the eATLAS app. 
  1. Post skate or whenever you need a warmup, walk north on Michigan Avenue to take in some holiday lights and treat yourself to hot chocolate. After extensive research over previous winters, I can confidently recommend the best hot chocolate in the Loop at Fannie May Chocolates at the southeast corner of Michigan Avenue and Upper Wacker Drive. They make it several times a day by melting their signature chocolate in a special hot chocolate machine. The key to this cocoa beverage is the chocolate wafter (either milk or dark, your choice) offered with the drink. Be sure to drop it into your cup before consuming. As it melts, the added chocolate will turn the drink into delightful viscous cocoa heaven! If you are a real chocoholic, consider immersing yourself with the Chocolate Scavenger Hunt in Chicago
Photo by @chicitigirl
  1. It’s rare for us city dwellers to have a fireplace in our home so we love venturing out to enjoy a toasty fire. One of my favorite spots has 3 grand fireplaces, the lobby at the Chicago Athletic Association on Michigan Avenue. This grand building was constructed in the early 1890’s and was a Men’s-only Athletic Association converted in 2015 to a hotel. The stunning German-designed lobby on the second-floor doubles as a restaurant bar called Drawing Room. It’s wood-lined, dark and dimly lit and filled with library tables and snuggly chairs and sofas, providing the perfect ambiance for a cozy fire. Grab a cocktail or some bites and hunker down near one of the 3 fire hearths. 
  1. Visit Chicago’s largest and most famous holiday-lit department store on State Street, Macy’s. Formerly the beloved Marshall Field & Company department store, the decorations start outside along State Street with massive trumpets and decorated windows. Be sure to wander inside where the first floor brightens with red carpet, bulbs and décor. Also, hop on the elevator to the 7th floor to see where Holiday magic awaits akin to The Elf movie. The floor seems to be from Santa’s village with ornaments, toys and presents luring children of all ages. Venture over to the Walnut Room restaurant to see the massive store tree and if you’re able, grab a table to sample some of the restaurant’s famous dishes Mrs. Hering’s 1890 Original Chicken Pie and Frango Mint cheesecake.  
Photo by @chicitigirl
  1. Finish the night with more twinkle and perhaps a cocktail. City folks have been visiting Butch McGuires on Chicago’s storied nightlife row, Division Street, since the 1960s when they first began decorating. Here, decorations cover the ceiling and include working toy trains and tens of thousands of lights. The menu is pretty simple but there’s a drink that’s deemed a  “world famous holiday concoction”, called Christmas In Your Mouth. Ordered as a shot or martini, the green eye-opener includes Rumplemintz, Bailey’s and Crème de Cacao. You can even order a bottle to take home! 
Photo by @chicitigirl
  1. If your game to keep going, start up a tradition started years ago by some of my friends, a hotel bar holiday decorations crawl. It’s a great way to see some impressive holiday decorations in places not regularly visited by locals. Some of our favorites include Lockwood lobby bar at Chicago’s longest operating hotel, the Palmer House, where you can get an old-fashioned cocktail inspired by the brownie, the dessert invented inside the hotel’s kitchen back in 1893 for the Columbian Exposition/World’s Fair. If city views are your desire, make sure to make the Langham Hotel bar, Travelle, a stop where you can overlook the Chicago River from your second-floor perch. On trend with the mocktail movement, many hotel bars feature alcohol-free beverages, like Virgin Hotel’s Cerise Rooftop bar. Their “Babes in Toyland” holiday pop up features Mocktails like “Prickly Fizz” and “The Good Apple”. 

Whatever you decide to do, just be sure to layer up and leave some room in your stomach for all of Chicago’s food and drink options.  

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