Christmas in Chicago: Sage Advice on Spending the Holidays in the Windy City

Christmas in Chicago: Sage Advice on Spending the Holidays in the Windy City

Chicago is a great city to enjoy the Christmas season. The lights, the snow, the decorations combine to create the holiday atmosphere America is so famous for.

“He pulls out a candy cane. You pull it a gingerbread cookie. He sends one of yours to the nativity scene. You send one of his to Santa’s Village. That's the Chicago way.”

The Windy City, Second City, Chi-town, Chicago. The only place in America where a cow can be accused of arson and the pizza is done upside down. Chicago has its own unique mystique; it's own convoluted way of sorting out. A distinct aroma, smell, and a perfume of high intrigue.

Build upon the ashes of the old. Square Tetris blocks piled one on top of other. Chicago never gives up. Never backs down. Never quits.

It's old and new, mix and matched into the now and waiting anxiously for the tomorrow. It's Kanye West belching out old time Sinatra lyrics. It's hot-dogs that hit all the major food groups with their toppings and, just for kicks, invent a few more along the way. In God they trust, followed closely by the Blackhawks. Home of The Bean, the Chrysler Building, and Sears Tower. Donald Trump’s highrise playground. The hamlet, where winter resembles Narnia. The Miracle Mile where everything is on the table and nothing is off the rack.

Chicago is a city of extremes. Of odd juxtaposition and strange comparisons. Chicago is a city that takes everything the world has and adapts it to its own mercurial makeup. It does the holidays right. It’ll scare your pants off in Halloween. Blitz you out come St. Patrick. Romance you into a shotgun wedding on Valentine. And, finally, stuff Martha Stewart’s Christmas dream down your throat.

- Disclaimer: to really get this sketch described properly, this last bit of scene stealing imagery has to be done with a crank of your imaginary workshop. You have to picture great oath of a man, wearing a Sox uniform and a Santa hat, all the while holding you down and waving his fist to the heavens. Big strong voice, “Buddy, you will love Christmas. Or so help me Derrick Rose!”

Then, on saying the sacred name, he crosses himself and intones a quick Hail Mary. That's Chicago for you, the love old Saint Nick, but in a straight fight, Derrick Rose has that pudgy fella' beat.

Official Christmas Tree Lighting Ceremony


Charge: Free

Usually on the week of Thanksgiving.

Christmas tree lighting ceremonies are like the starting shot to the holiday season. It's that big neon flare up that gives you permission to start acting like a bozo and begin sporting your deer antlers to the office. It's a way for everyone in town, to officially, get the all-clear from the bureaucratic mucky mucks.

"Fellas, we just got the thumbs up. Time to act like nutbars. Crack open the eggnog!"

It's no wonder that when Christmas rolls around, every city in America makes a big show of firing up their pine tree. Chicago, the place where Al Capone flicked the Federales off, is no stranger to this ritual.

For over a 102 years, the bigwigs have spruced up their tree, with all the clatter afforded to them by their budget. Since 1966, this custom has taken place at Daley Plaza. In 2015, someone may have misspelled the address, or simply started celebrating with liquid help far too early in the season, because the celebration has taken a wrong turn and ended up at Millennium Park.

Next year? Who knows.



Washington and Dearborn Sts

Inspired by Nuremberg, Germany, this festive traditional open air market is the equivalent of Oktoberfest in December. Iconic German knick-knacks, buxom Anglo babes, cuckoo clocks, honeyed wine and enough beer to fill the Great Lakes.

Christkindlmarket—try saying it ten times in a row—is simply one more reason for Chi-town to party hearty. Sure, it has its devoted family friendly fanbase, but at the heart of any German influenced fest, there is always the not so distant possibility of drunken revelry.

Ugly Sweater Run


One of those odd traditions that I still, as a legal alien in America, haven't managed to wrap my head around. Why, in all that you hold holy and sacred, are you constantly giving out God-Awful sweaters when the holiday season rolls around? Is it some sort of stigma of the past? Did General Washington beat back the Redcoats with the mighty power of a tacky Rudolph on his uniform?

Is it some sort of Kryptonite against bad omens? Or a way of gifting the year to come, with good fortune?

Whatever the case might be, I'm certain all of us have a shameful fashion suicide safely barricaded in the back of our closets.

Thankfully, the good folks in Chicago have formed a way of beating back the moths and putting this stylish suicide to good use.

The Ugly Sweater Run is a 5k sporting event design for the sole purpose of getting our jollies into gear. Snatch your ugliest and itchies grandmother token from those boxes in the attic and prepare to sweat out the Thanksgiving turkey, as you race headlong into a finish line stuffed with tables full of hot chocolate and refreshing beer. In other words, it all balances out in the end.

By the way, the price starts of a 40 bucks.

Grogg Time

5210 N Clark St .

If you are a fantasy fan, one of those strange fellas' that has actually read every one of Martin's "Song Of Fire and Ice" books, then you certainly know what Grogg is.

Now, as you retrace your "Game of Throne" trivia, the question you have to ask yourself is: have you actually had Grogg or mead?

Have you partaken of the hero's libation? Have you tasted the manna of the gods? Because in Chicago, this drink flows like moonshine during prohibition.

One of the best places to sit down and enjoy the holiday beverage is at Simon's Tavern. A dive bar that caters to everyone and anything. So, sip thoughtfully from this hot-mulled wine as you share the holiday cheer with the friendly locals.

Morton Arboretum Holiday Lights

4100 Illinois Rte 53, Lisle.

$12–$20, kids $6–$13.

You just know, deep down in your gut, that someplace, or somethings, were made for a particular set of people in mind. A very unique niche in the market that the smarty-pants entrepreneur rails to control.

Morton Arboretum Holiday Lights, like Pink Floyd's "The Wall", The Beatles "Yellow Submarine", and parts of "2001 A Space Odyssey", were intentionally crafted with the stoner in mind. There's no way to actually pass off this spectacle as anything other than that. Yes, it's suppose to be all family friendly. Yes, the locals will point out that the LED fanfare has been cultivated with the little ones in mind.

But, come on, let's be honest, this psychedelic, one mile, mix match of lights, sounds, and animatronics, would make Jim Morrison proud.

Enjoy symphonic suites, like "The Nutcracker", as your eyes bug out of your head and you're left wondering where your mind has drifted to.

Indoor and outdoor ice skating rinks

Christmas in Chicago is nippy at best. At worst it's as if every time the wind blows Frosty the Snowman sucker punches you in the face. To say it's a cold, cold, cold, is to be kind to the insane temperature drops this city experiences in December.

So, it should come as no surprise, that one of the most easily accessible activities during the holidays is to Ice Skate. Here, in Chi-town, all you truly need to make a rink is a patch of flat land and a trusty bucket filled to the top with water.

These places spring up like dandelions through the Boroughs. You would need a phonebook sized list just to name them all. Instead, since I have to give you some credible and useful information, I'll simply shout out a few of the classic (classics, in layman's terms, also mean costliest).


- Millennium Park
- Maggie Daley Park
- Lincoln Park Zoo
- Parson's Chicken & Fish
- Wentworth Park


- Centennial Ice Rinks
- Glenview Ice Center
- Skatium Ice Arena

Directions? Too many to name and write down. Unholster your smartphone and give a shout out to Siri or Google, they'll guide you better than any website. After all, wasn't that what you were going to do in the first place?

Music Box Christmas Show

3733 N Southport Ave
$13 single feature, double feature $20

There's nothing else more profoundly Christmasy than movies. Every time the season sludges into the calendar, every cable channel flicks on the nostalgia meter and hopes the ratings will crank up.

We get hundreds of specials through the month of December TV shows banking on the fact that a cute tree will divert our attention away from the fact that the plot makes absolutely no sense. Old celebrities and new musician's banking on our need to relieve our old Santa glory days. An entire industry devoted to making Christmas into a healthy profit margin.

Well, Chicago does not shy away from a good money making opportunity. The Music Box, an old time theater, casts away all pretensions and gives the viewers a two for one deal. Starting on December 11, this mighty landmark, will showcase two classic Christmas movies in a double feature performance (two for the price of one). Each year they rotate, so your best bet is to call in advance or check their website (

Sing along with the patrons, rile up your festive cheer during the intermission and bask in the company of strangers as the season brings you all closer.

This Chicago tradition harks back to olden days and even Santa is likely to make an appearance during the shows.

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