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The holidays are always my favorite time of year. The mundane becomes the magical. And nowhere is that transformation more evident than in the city of Chicago. The steel and concrete landscape suddenly becomes awash in greenery, twinkling lights, and ribbons and glitter. Though the other 10 months of the year can be stark and modular, for these two months during the holidays, it’s completely enchanting.
Chicago goes all out for its holiday festivities. And we’re tallying up our favorite, can’t miss, things to do with kids and families on your holiday trip to the Windy City, Chicago.
Zoo Lights @ Lincoln Park Zoo
Even during standard, non-holiday times, the Lincoln Park Zoo is an awesome experience. There are very few zoos in the world that are located right in the heart of a booming metropolis and offer free admission on top of that. As locals, it continues to be one of our favorite things to do as a family and with out-of-town guests. And the Lincoln Park Zoo Lights is one of our favorite holiday traditions as a family.
Though perhaps smaller than most zoos, the Lincoln Park Zoo still boasts a wide and exotic assortment of exhibits, with everything from zebras to gorillas just chilling in their urban habitats. Their zoo lights display is absolutely beautiful with the Chicago skyline serving as a backdrop. Tons of illuminated displays light up the zoo’s interior, including a giant light tunnel, an under-the-sea adventure, and a path of candy canes.
There are also photo opportunities with Santa, seasonal refreshments, and plenty of educational stops along the way to learn more about the zoo’s year-long residents.
For families with small kids, the Lincoln Park Zoo Lights is a must-do and always gets rave reviews.
The Christmas Tree Lighting and Magnificent Mile Lights Festival
While it’s no Rockefeller Christmas Tree, the Christmas Tree in Millennium Park in downtown Chicago is equally as beautiful — and with its own fireworks show to boot! Traditionally taking place the weekend before Thanksgiving, the festivities also include the Magnificent Mile Lights Festival and parade. In recent years, the parade has become the third largest in the country, with millions of people showing up to watch the spectacle that begins at the top of Michigan Avenue by Oak Street Beach and slowly makes its way down to Wacker Drive beneath the glow of millions of twinkling holiday lights.
The parade always includes notable appearances by Mickey and Minnie Mouse, Kermit and Miss Piggy, and the big man himself, taking a brief trip away from the North Pole to enjoy the event with Mrs. Claus.
It’s a fun event that kicks off the holiday season and gets everyone excited for the weeks to come.
Ice Skating at Maggie Daley Park and Millennium Park
Want to get your skate on? Downtown Chicago has not one, but two ice skating rinks in Millennium park that are open to the public.
The traditional McCormick Tribune Ice Rink in Millennium Park is a perennial favorite among locals and tourists alike. Skate in the shadow of the famous Cloudgate (or Bean as it’s lovingly nicknamed) and the downtown skyline. Admission is free if you bring your own skates. Rental skates are also available. Once you’ve skated yourself hungry, you can pop into the Park Grill located right next to the rink for a meal or swing by the Park Café for a snack or hot beverage.
The other rink is newer and just as unique an experience. The Maggie Daley Ice Skating Ribbon is a thick stretch of ice rink that literally ribbons around and through Maggie Daley Park, allowing you to tour the entire park while you skate. Just a block or two from the McCormick Tribune Ice Rink, you could easily try your hand at both and pick your favorite. Both rinks are kid friendly and great for the whole family.
The Nutcracker at the Joffrey Ballet
A few years ago, for my birthday (which happens to fall during the holidays), my husband got us tickets to see the Nutcracker performed by the Joffrey Ballet company. We’re theater buffs who are known for scoping out the best on and off Broadway shows, but the Nutcracker by the Joffrey Ballet was one of the most amazing performances I have ever seen.
The Nutcracker in general is a spectacular show. The score by Tchaikovsky is legendary and some of the most renowned holiday music out there. And the story itself is so magical and full of wonder. But what I was particularly taken with was how the Joffrey told the story. Every ballet company tells it differently and puts their own performative spin on it. But the entire show, from the set to the costumes, was nothing short of mesmerizing.
You simply haven’t seen the Nutcracker until you’ve seen it performed by the Joffrey.
You simply haven’t seen the Nutcracker until you’ve seen it performed by the Joffrey.
Christkindlmarket at Daley Plaza
The Christkindlmarket is far and away one of my favorite holiday activities to do in Chicago, second only to going to the Christmas tree lot by Big Star Tacos in Wicker Park to pick out our tree. Inspired by the German Christmas markets of Europe, Chicago’s Christkindlmarket is the largest in the US, attracting over a million visitors every year.
For someone who loves to travel, the market is like getting a small taste of Europe at home. The market is set up in the heart of the Loop in Daley Plaza. There are a plethora of artisans and crafters who set up shop at the market, selling beautiful handmade Christmas ornaments, nativity scenes, dolls and wooden toys, and a variety of other treasures.
Also on hand are food vendors, specializing in all the European favorites, including schnitzel, hot pretzels, hot cocoa, and my very favorite gluhwein, which is a mulled wine that is often found in Switzerland, Germany, and Austria.
It’s become a tradition for our family to visit the market every year and pick out a new ornament or two for our tree (last year’s ornament was one that looked like our dog, Ruby) and enjoy some classic German treats, including cocoa and gluhwein (for my husband and I) served in the annual keepsake mugs that we’ve taken to collecting and display on our mantel at Christmas.
This year, in 2020, the market has gone virtual, which means anyone can find beautiful handcrafted gifts and ornaments without even leaving the comfort of your home. But I’m already counting down the days to next year and returning to the market in person.
Window shop on Michigan Avenue
I’m a bit of a Scrooge when it comes to holiday shopping. I avoided the mall like the plague even before we had a literal one on our hands. Going to a store to shop for the holidays gives me flashbacks to that movie Jingle All the Way with Arnold Schwarzenegger, particularly the scene where he’s struggling to make it out of the ball pit.
But sometimes it’s nice to holiday shop for the experience instead of for the necessity, perusing the windows not because you’re looking for anything in particular but just because you enjoy the decorations and displays.
Michigan Avenue is arguably one of the best places to do this, with over an entire magnificent mile of glittering storefronts decked out for the season. Never a city to skimp on street decoration, even in the summer, Chicago definitely doesn’t disappoint in the winter, with all sorts of festive displays lining the sidewalks. We highly recommend setting aside an afternoon for just walking the avenue, maybe stopping by the new four-floor Starbuck’s Roastery for sustenance and hailing a horse drawn carriage ride up by Watertower if you get tired.
It’s completely free and sure to get you and your family in the holiday spirit.
Every year from early December through the middle of January, the ever popular Navy Pier transforms into a magical winter wonderland as part of the Winter Wonderfest at Navy Pier event. And the great part is, the majority of the experience is indoors (so you don’t have to deal with those brutal Chicago winters you’ve heard so much about). Tons of decorated trees, countless strands of twinkle lights, and all sorts of festive decorations make the normally generic looking Navy Pier seem almost as spirited as the North Pole. Almost.
With everything from carnival rides and an indoor ice skating rink, inflatable bounce houses and rock-climbing walls, it’s the perfect spot for kids of all ages to get into the holiday spirit. And when it comes to the classic holiday activities, Winter Wonderfest checks all the boxes. You can get your picture taken with Santa, enjoy steaming mugs of cocoa, and listen to groups of carolers as they make their way through the fest.
It’s a memorable experience that’s not to be missed!
When You Go
Chicago is a great long weekend trip from L.A., with direct flights offered by all the major airlines. If you’re looking to go all out on your adventure, we recommend the Waldorf Astoria in Chicago’s Gold Coast district (and we also recommend treating yourself to a massage at their fabulous spa if you have the time). For a budget-friendly option that’s also centrally located and easy for getting around, you can’t go wrong with the Hampton Inn — Chicago Downtown location. It’s right on the river and just off of Michigan Avenue. Looking for a unique hotel experience? Check out the Chicago Athletic Association Hotel housed in the refurbished former headquarters of the Chicago Athletic Association, right across from the Bean.
If you’re looking for a weekend destination that’s sure to get you in the holiday spirit, Chicago can’t be beat! Please note that due to changing COVID conditions in Chicago, some of these events might be virtual only in 2020. Please refer to event websites for up to date information on the status of these events.
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