The City of Chicago’s annual Christmas Tree Lighting began in 1914, and what better way to see in the holidays? Originally installed in Grant Park, the tree was actually not one, but multiple smaller trees combined. Later shifting its bauble-adorned location to Daley Plaza, in 2009 the tree ceased to be an evergreen jigsaw, instead represented by one large, individual tree. And it’s not any old tree, either: like a forest edition of American Idol, Chicago’s Christmas Tree is selected via a public contest, with any needled entrant needing to meet the criteria of being ‘at least 55 feet or taller, located less than 100 miles from Chicago’s Loop, and preferably a sturdy Spruce or Fir tree.’ Crikey!

This year the ceremony will take place in Millenium Park, where the tree’s already myriad lights will be multiplied through its reflection in that curvy wonder, The Bean.

The Museum’s Christmas Around the World and Holidays of Light exhibit is really lovely: an awe-inspiring four-storey Grand Tree surrounded by 50 smaller trees, each decorated (by volunteers, no less) to represent the holiday traditions of cultures from around the globe. Which seems a fittingly festive way to celebrate goodwill to all men (and women), thinking of our fellow humans’ Christmas, wherever they are in the world.

If you have museum membership, you could also partake in the festive feast that is the Member Holiday Breakfast, eating in this twinkly forest, while serenaded by carollers. You’ll also get to enjoy holiday-themed crafts - and could visit with Santa, who’ll also be spending a spell amongst the trees!

The Walnut Room at Macy’s was the first restaurant to be opened in a department store. Now a destination in itself, the world-famous dining room is known for its swell holiday decor - including a 45 foot Great Tree, which adds stately festive elegance to the proceedings.

Immerse yourself in nature, the great outdoors and the spirit of Christmas with the Chicago Botanic Garden's Lightscape event. You'll be able to walk through incredible outdoor light installations created specifically for this exhibit. Wander through canopies of golden lights, sparkling trees and illuminated stars - and feel like you're living inside a Christmas tree for the evening!

A Wonder to behold, Light Up The Lake will have you giddy with festiveness. An awe-inspiring winter wonderland, you’ll find a skating rink, carnival rides, and plenty of holiday-themed activities. Past attractions have included the deliciously-named Candy Cane Lighthouse, Hot Cocoa Cups, Kringle Carousel and Reindeer Express (kids’ rides), Holiday Howdy Horse (photo opportunity), and Aquafina® Create-A-Cookie Cottage (where little ‘uns can decorate their own freshly baked Christmas cookies). There’s also a Ferris Wheel, which doesn’t have a jolly or alliterative name, but looks especially awesome.

Well, tickle me with a candy cane and call me Buddy - is this not one of the most whizzbang wonderful things you’ve ever encountered? A uniquely Chicago tradition, the CTA Holiday Train first took to the tracks in 1992, when employees displayed a ‘Season’s Greetings from the CTA’ sign on a service that was delivering food to charities throughout the city. It’s become increasingly elaborate since then, with Santa and his reindeers leading the charge from a flatbed carriage, cars filled with lights, decorations, and advertising fit for residents of the North Pole, plus CTA elves bobbing through the train, spreading festive cheer and buckets of candy.

Having been saved from two rounds of budget cuts - how’s that for holiday spirit! - Santa’s Express is now accompanied by recent addition, the Elves’ Workshop Train (there’s a holiday bus, too!). Taking a trip on all the CTA’s lines, the train usually runs from late November ‘til just before Christmas (because obviously then Santa will need to be gearing up for a more international journey). Keep an eye on the CTA website for schedule details.

Melting marshmallows, this just gets more exciting! It’s not only the CTA that has festive wheels a-spinning, there’s also the Polar Express, helped into motion by the gang at Amtrak. Departing Chicago Union Station at varied times from the end of November ‘til January 1st, those clambering aboard the Polar Express will be taken on an hour long trip, packed with festive magic that reflects the ride in the infamous book. Golden tickets, dancing chefs, carolling… it’ll be a fun-packed festive experience. Oh, and passengers are encouraged to wear pyjamas (you can even buy a special set from the Polar Express website - how’s that for merchandising, eh?).

Quite the sight to behold, Illumination takes you on a tour through the tree lights at The Morton Arboretum. No typical lit firs or spruces, the colorful, changing displays are breathtaking. And this year the ever-popular (or should that be evergreen?) experience includes new features, such a hugging a tree (hugging a tree!) to see how it responds, and watching multicolored lights dance to symphonic music. There’s also the IllumiBrew event, where as you amble through the trees, you can sample seasonal beers from local breweries. Though if a warming cocoa is more your cup of tea (sorry… muddling hot drink metaphors there), you can also cozy up by a crackling fire with that while you roast marshmallows for s’mores.

The extraordinary 2.5 million lights on display are incredible - and they’re not all there is to see as part of Lincoln Park Zoo’s traditional ZooLights. There are musical light shows, strolling carolers, warm spiced wine ‘n’ frosty beers, live ice sculpture carving, plus Candy Cane Lane and over one hundred giant, themed displays. So plenty to be dazzled by in addition to the lights (and don’t try to count them - it’s a fool’s errand, and will make you dizzy).

Of course, it’s not just the official city lights that make you gasp with merry wonder.... Head to Lincolnwood Towers for some marvels of holiday illumination!

This wonderland for festive shoppers was inspired by the Christkindlesmarkt in Nuremberg, Germany, one of the first holiday markets of its kind, which began in 1545 (how’s that for history!). Established somewhat more recently - in 1996, to be exact - Chicago’s Christkindlmarket was the elfy brainchild of the snappily-titled German American Chamber of Commerce of the Midwest Inc (GACC Midwest). The perfect place to get you in the holiday mood, and get your Christmas shopping done, the market is packed with gift inspiration and tasty treats for when you need a warming mid-shop pick me up.

While there, you may even catch a glimpse of the ChristKind, the market’s namesake, who is beloved in Germany, and known for handing out gifts, like Santa (no red suit for her, though; she opts for a rather more ethereal get-up, which did make me wonder if she gads about town with Glinda from The Wizard of Oz). The ChristKind will be gliding around the market ‘sharing German holiday traditions and telling Christmas stories.’ You can also snap up some Christkindlmarket merchandise, including the pretty spectacular boot shaped mugs.

Plus, for the jolly juniors in the family, there’s the free-to-join Kinder Club, gaining access to activities and events at the market.

An eclectic bazaar comprising more than 125 vendors, there are all sorts of delights to be found at the Randolph Street Holiday Market (the non-holiday market here usually takes place on the last weekend of each month). For unusual, less run-of-the-mill gifts, take a gander through the selection of new and vintage housewares, fashion, art and decorative items, plus plenty more besides. There’s free parking, making it that much easier to carry your swag home. Oh, and you might want to visit the market bar, because, after all, Christmas shopping is thirsty work (it’ll be a virgin bloody mary for you if you’re driving though, obviously).

Randolph Street isn’t the only market with a smorgasbord of gifty goodness awaiting you. At the One of a Kind Holiday Show, 600 vendors will tickle your shopping tastebuds with their delightful, handmade wares. Prepare to be inspired - and take a large tote with you.

There's nobody who encapsulates the holiday spirit better than Will Ferrell's loveable character Buddy the Elf.

Now, Buddy's antics can be enjoyed in musical form during this incredible show, playing at Drury Lane Theatre. A great option to keep the little ones entertained this holiday season, Elf the Musical follows the same heart-warming story of the original film while peppering it with catchy songs. Bring the family to see Buddy the Elf journey from the North Pole all the way to New York City to find his real father. After this performance, the whole family will be full of festive cheer.

Enjoyed for more than forty years - by a staggering 1.5 million theatergoers! - Goodman Theatre’s A Christmas Carol is a true holiday classic. Telling Charles Dickens’ tale of that miserly grumpy-drawers, Ebeneezer Scrooge, the moms of everyone (ever) involved must be extraordinarily proud, not least because the reviews are uniformly glowing. ‘Never fails to touch one's soul," said the Chicago Tribune (frankly, that description alone is enough to make me blub), ‘Leav[es] us utterly besotted with holiday spirit,’ enthused the Chicago Reader, and very merrily, Theatremania.com exclaimed that it’s ‘As jolly as ever’ (I love the word jolly; anything dubbed as that is a winner). And what all this tells us is that you should definitely gad forth to the Goodman Theatre this Christmas.

Whatever anyone says, the 1980s gave us some truly marvelous things. One of those was the Music Box Christmas show, which first began on a snowy Christmas Eve in 1983. Legend has it (well, actually, the tale is told on the theater’s website) that the Music Box’s manager decided to screen a couple of old holiday films, filling the intermission with some impromptu carolling. It’s become a tradition that’s still going strong, with moviegoers greeted by Santa, who leads them in some merry carol-singing, accompanied by organist Dennis Scott. And for those who find themselves fa-la-la’ing more than they intended, don’t fret: the lyrics are projected onto the cinema screen so everyone can sing along (isn’t this already sounding so amazingly festive that you could almost cry?). Then onwards to a screening of White Christmas, or It’s a Wonderful Life - or, if you can’t get enough festiveness and fancy a double-whammy, you could stay for both!

Also, this holiday movie extravaganza is obviously mind-bogglingly splendid enough to attract festive folk with a positively magnetic force (like, um, a cat to the Christmas tree lights), but there’s also the theatre itself, which opened in August 1929, just two months before the Great Depression. So as you take your seat you can marvel at your surroundings, and wonder: who else sat here before me? Because the time travel isn’t just in the on-screen holiday classics. Magic.

From one evocative experience to another…. and this is utterly glorious. Since 2002, the American Blues Theater has regaled Chicago’s holiday audiences with a live 1940s radio broadcast, recreating Bedford Falls with the magic of Foley sound effects, an original score, and Christmas carols. Time-traveling wonder which is magical and adorable.

No Christmas would be complete without a production of The Nutcracker, and Chicago’s is a vivid, sugarplum dream. Joffrey Ballet’s imagining, choreographed by Christopher Wheeldon, is set during Chicago's 1893 World's Fair, a tale that follows ‘young Marie and her mother, a sculptress creating the iconic Statue of the Republic.’ And how does their Nutcracker unfold, you might ask? Well, ‘as they prepare for their annual holiday celebration, a visit from the charming but mysterious Great Impresario sets off a Christmas Eve dream of whirlwind romance and adventure.’ Already a holiday must-see, Joffrey Ballet’s interpretation is fittingly magical and wonderfully unique.

Here’s something with a feel-good factor: That’s Weird, Grandma shows comprise songs and sketches written by Chicago school kids. Created by not-for-profit organization Barrel of Monkeys, who provide arts education programs to students throughout Chicago, That’s Weird, Grandma features adaptations of stories conjured up during their creative writing residencies in elementary schools, which are then performed by BOM’s company of professional actors and musicians. In addition to the original show and the holiday edition, there are other variations, too, including That’s Weird, Grandma: Star-Studded Stories (runs January 20th-February 17th 2019), That’s Weird, Grandma: Stories That Sing and Dance (May 3rd-25th 2019) and That’s Weird, Grandma: Fantastic Beasts and the Stories About Them (June 24th-August 12th, 2019).

The Arthritis Foundation’s Jingle Bell Run is the longest-running holiday-themed 5k race series - it’s also a very jolly way to raise funds to help cure the #1 cause of disability in America. And a particularly great fact is that you can run (or dawdle) knowing that the full 100% of your registration fee and fundraised dollars will go the charity’s work.

Incidentally, my favorite note on the Jingle Bell Run’s website is the suggestion of ‘[Tying] jingle bells to your shoelaces’!

You could also check out this Urban Matter guide to other holiday races.