Tinsel Gingerbread Raclette
Things to eat, drink and do to make the most of Holiday Time in Chicago.
I’ve bounced around Chicago long enough to know that there are far better things to do in this city during the holidays than just hang out at the holiday pop up bars.
There’s lights to admire, parties to prepare, cheer to spread.
There’s Tom & Jerry’s to savor, raclette to relish, Santa Trains to track down.
There’s sledding, sightseeing, shopping, tippling, tea timing, and treelighting to enjoy.
Friends to be met. Gifts to be given. Dining to be done.
These days, most places spruce up their bar or restaurant with some holiday decor, but some are better than others at achieving a certain, festive, atmosphere, and the charm is not always relative to the amount of lights that get strung.
Below I’ve collected my favorite places to go and things to do during the holiday season in Chicago. Most of these can flex to be enjoyed by a small group of adult friends, or they work just as well with a family. Even Butch Mcguire’s has a kids menu if you can believe it.
It’s fun to string a few of these things together in an afternoon or evening—shop here, duck into a bar there, challenge a stranger to a curling match at the next spot. There’s worse ways to spend a Saturday in December than hopping to as many bedazzled barrooms as you and your pals can muster.
Or simply see how many larger than life decorated Christmas trees you can find. Here’s a head start..Millenium Park, Macys, Daley Plaza, Gallager Way, Bloomingdales, Lincoln Park Zoo, etc.
Chief O Neill’s - Yes, this place is an Irish pub, but it has a solid food menu, it’s family friendly, and the holiday decor is off the charts.
Club Lucky - This classic Italian supper club gets decked out for the holidays.
Marie’s Pizza & Liquors - This restaurant with its own liquor window is quirky and old school and wonderful and though it has been temporarily closed since September, the owner insists it will reopen soon so I’m putting it on this list because its holiday decor is literally unmatched in the city of Chicago.
RL - The Ralph Lauren restaurant is wonderful to visit year round, and although I don’t believe they put up a single holiday decoration, the bustling vibe that is mere steps away from the lights of Water Tower and Michigan Avenue feels just right during the holidays.
Walnut Room - Patrons dine around a multi-story Christmas tree in this world famous room on the 7th floor of Macy’s. Breakfast, lunch and dinner reservations normally sell out for the month long season, but you might be able to squeeze in a seat at the wine bar.
Butch McGuire’s - Every nook and cranny of this classic Chicago tavern gets the Christmas treatment.
Chicago Athletic Hotel - The classic swimming pool on the ground floor of this impressive hotel turns into a festive holiday dive bar called “Happy’s” all month long.
Clark Street Holiday Pop Up Bars - Along the Wrigleyville stretch of Clark Street between Roscoe and Waveland, multiple bars transform entirely into holiday themed destinations where you can find everything from Christmas tree-shaped waffles (Elf’d Up) to Jingle Juice (Christmas Club Chicago).
Dmen Tap - Krampus takes over this Avondale bar all month long with mulled wine, Revolution Brewing’s Fist of Krampus holiday ale, raclette sandwiches, etc.
Frosty’s Christmas Bar - Multiple holiday-themed bars, dance floors and all around debauchery near Goose Island.
Glasgott’s Groggery - A wonderful room in which to spend a holiday happy hour. And if you stick around a while, do yourself a favor and order in from Athenian Room next door.
LondonHouse “Rudloph’s Rooftop” - It’s tough to beat the city and river views from the rooftop igloos.
Miller’s Pub - Two words: Tom & Jerry (or is that three words?).
Palmer House Hilton - This lobby is the lobby to end all hotel lobbies. Grab a cocktail from the bar and soak up the grand, old school ambiance. If you’re lucky, you might catch a holiday performance by the Chicago Children’s Choir.
Z Bar - This rooftop bar at the Penninsula offers great views of the holiday lights along Michigan Avenue.
Pink Squirrel - This retro bar goes into tinsel overload during the holidays. And there’s duckpin bowling.
Smith & Wollensky - The bar of this fine steakhouse along the river is a great place to duck into if you are checking out the downtown holiday lights.
Shaw’s - This Chicago institution is one of the premier places in town for seafood, but the bar is also a great place to grab a cocktail during the holidays.
Caldwell Woods - The warming shelter here has one of the most amazing fireplaces in the city, but it is unfortunately not slated to open until after winter. Still, the sledding is decent and you can combine the excursion with a stop at nearby Superdawg afterwards.
Chicago El “Santa Train” - Feel like a kid again if you can manage to track down a fleeting ride on the one and only “Santa Train” as it passes through your neighborhood. Click the link to view the schedule.
Cricket Hill - The wind off the lake might not work to your favor, but otherwise, this is a pretty epic sledding hill.
Daley Plaza Christkindlmarket - This version of a traditional German Christmas market in Daley Plaza is not to be missed for its unique candy, ornament and gift shops, beer halls, and cultural performances.
The Drake - Holiday Afternoon Tea service taken in the Palm Court of the historic Drake Hotel is worth an annual pilgrimmage.
Harry Caray’s Tavern “Lakefront Lodge” - If you have a group, bring your brood to the Navy Pier outpost of this famous tavern where you can have your own heated igloo, curling rink, fire pit, hot chocolate bar, and views of the lake.
Lincoln Park Zoo Lights - This remarkable experience where you parade yourself at night through the zoo which has been decked out in millions of Christmas lights is free, accessible for all ages, and you can buy booze.
Macy’s State Street - Even if you don’t buy a thing, passing through the first floor of the State Street Macy’s and admiring the multi-level view above should get you in the Christmas spirit.
Maggie Daley Park “Skating Ribbon” - Getting a ticket to access the site can be a pain, but this totally unique “Skating Ribbon” gives you the sensation of ice skating along a windy frozen river rather than simply going in circles on a rink.
Music Box Theater - This crowd-pleasing tradition includes a glorious full screen technicolor showing of Sound of Music in the historic Music Box theater and everyone sings along to each song. Don’t miss the vocal warm up before the movie with the in-house organist.
Wrigley Field Winterland- The Friendly Confines turns into the Wintrust Winterland with activities both inside and outside the stadium including a holiday market, skating rink, ferris wheel, carnival rides, and sledding hill. A couple treats not to be missed are the Belgian hot chocolate and the saucisson sec raclette sandwich.
Symphony Center “Home Alone in Concert” - Don’t miss this unique opportunity to watch the Christmas Classic while the Chicago Symphony Orchestra performs the delightful score.
Trump Tower Gingerbread Express -
It will only last about 15 seconds, but it’s still worth a look if you are in the area to ride this elevator that is entirely bedecked with actual gingerbread. When you arrive at the 16th floor, you might as well grab a drink at the bar and take in the view.
