Holidays in Chicago | Loews Chicago Hotel

Where do we begin with things to do in Chicago during the holidays? From activities for the little ones to festive fun times for the adults, there is plenty to do to help spread the holiday cheer.

Downtown Chicago Festivities

If you’re visiting Chicago with pint-sized travelers in tow, taking a 10-minute walk from Loews Chicago to Navy Pier for the annual Winter WonderFest is a great start. This event’s claim to fame is that it is the city’s largest indoor playground with over 170,000 square feet of space, home to an ice-skating rink, giant slides, rides, holiday treats and more! You must by tickets before heading over and they generally run about $23 for an all-day pass and $10 for the “Mini Pass,” which gives you the general admission access but limited access within the festival.

If indoor activities are not your thing then head south instead, to Maggie Daley and Millennium Park at the corner of Randolph and Michigan Avenues. The city did a wonderful job of updating the public parks last summer, adding Maggie Daley Park, one of the largest outdoor parks in the Chicagoland area.

The most unique feature of this park is the Skating Ribbon, which encompasses the summertime rock climbing structure. This isn’t your old-school typical oval ice rink; rather it’s a wavy ribbon-like design offering up a little more of a challenge to those that aren’t the next Nancy Kerrigan. Plus, the city-skyline photo opps are out of this world and make the perfect backdrop for that date-night selfie or family vacation photo. Admission is free; you just have to rent skates, should you not have your own, and off you go!


For those who just want to eat, drink and be merry, a must-visit holiday spot and my personal favorite is the Chriskindlemarket at Daley Plaza. Just a 20-minute walk from Loews Hotel and easily accessible from public transit stops, it’s a great way to experience a little bit of Germany in Chicago.


This place is almost always packed, especially on the weekends. Before you begin to wander through this winter wonderland, you should first get in line for the mulled wine and collectors mug. Each year, there is a new design and the mug has turned into a hot commodity over the holidays. (I shamelessly admit I have 4 already.) After you’ve warmed up with a beverage, peruse the dozens of holiday shops that sell everything from handmade ornaments to delicious caramel nut mix that is near impossible to pass up.


Rosemont for the Holidays

It’s not just downtown Chicago that has all of the holiday fun — Rosemont does as well! Situated just a 5-minute walk from Loews Chicago O’Hare is the annual Frozemont in MB Financial Park. From delicious bites by the local restaurants to ice skating, celebrity appearances and tube sledding, it’s all in an average day at Frozemont!


After a few hours of being out in the cold, I highly recommend getting toasty in a drive down Rosemont’s River Road and Higgins Road. The village has some of the most spectacular lights I’ve ever seen lining the streets — it’s like you walked into a Norman Rockwell painting. There are so many lights that they begin placing them on all of the trees all the way back in September.

Last but never least, if you left home without the kiddos getting to chat with Santa himself, don’t sweat it: he’s visiting the Fashion Outlets of Chicago, just steps behind Loews Chicago O’Hare. He’ll be ready and waiting at HGTV’s Santa HQ. Bring the whole family, young and old, to join in the festive fun.

Happy Holidays!