Winter Activities in Chicago
As you may or may not know, winters in Chicago can be pretty brutal. There’s freezing rain/sleet/snow, darkness before work, darkness after work, slippery sidewalks, falling icicles, you name it. It’s a dangerous, frozen tundra (Chiberia, anyone?), but there are ways we Chicagoans find silver linings to the cold weather.
Winter activities in Chicago range from the adventurous to the cozy and everywhere in between. There’s something for everyone in this beautiful city, especially during the holidays and that problematic time between New Year’s and springtime. So, without further ado, here are my personal favorite winter activities in Chicago:
- Skating at Maggie Daley Park: There are many places to go ice skating in Chicago, but Maggie Daley Park is probably the most unique. The shape of this rink is a ribbon set in a wavy circle with peaks and valleys set into the ice. Admission is free and skate rentals are $12 during the week and $14 on the weekends. This attraction has already opened for the year.
- ZooLights at Lincoln Park Zoo: Every year, Lincoln Park Zoo puts on a free event where guests can enjoy the zoo at night in all its twinkly light glory. They have winter activities for families, warm spiced wine and ice sculpture carving, along with all the normal zoo activities. ZooLights starts today actually, and is open select dates through January 7.
- Walk Down Michigan Avenue: Michigan Avenue can be one of the most magical, albeit crowded, places in the city during the holidays. Every space imaginable is decorated in twinkly lights and holiday ornamentation. Plus, it’s mostly free, unless you decide to partake in the many, many stores that line the Magnificent Mile.
- Christkindlmarket: This outdoor Christmas market is located in Daley Plaza downtown and his home to a ton of small markets selling holiday fare. Nestled in between the stores are vendors selling traditional German fare, hot chocolate and mulled wine. Even if you’re not in the mood to shop, this market is super fun to walk around while you sip your hot wine. It’s open now through Christmas Eve.
- Grab a Drink in a Cozy Bar: There are number of cozy places in Chicago to obtain a booze blanket to fight the cold. The best ones have a fireplace and comfy chairs for that extra homey warmth. My favorite bars for winter are Drumbar in the Raffaello Hotel (Gold Coast), The Broken Shaker in the Freehand (River North), and Scofflaw (Logan Square), all of which have excellent cocktails and cozy ambiance.

What are your favorite winter activities in Chicago?














































I’d never been inside when it was the Tokyo Hotel, but always passed it and wondered what went on behind its dingy exterior. A month later, there I was checking in at the upscale hostel/hotel. I had walked over after work on Friday; it was just a short jaunt over to the River North Neighborhood. The check-in process was casual and easy, and after a brief orientation of the property, I was on my way up to the tenth floor in a painfully slow elevator. I chose to stay in one of their private rooms, which they offer along with shared and private bunk-bedded rooms.
two small shelves of books ranging from “The Help” to “The Mammoth of Best New Erotica”, as well as a house phone, hotel guide, and a mini bar in an interior cabinet. The blue-tiled bathroom featured a stand-up shower, hairdryer, fluffy
higan Avenue, looking at menus and turning them down, hunger forced us to stop into Doc B’s Fresh Kitchen. Right off the bat, I wasn’t crazy about this decision. It seemed like an upscale TGI Fridays, only without the moderate prices. We sat down and ordered a couple of beers and decided whether or not we should bail. Again, hunger won and we had our beers and a kale and artichoke dip which was good in the way that artichoke dip always is. After we paid, we walked back up to Michigan Avenue just in time to finally be summoned to The Purple Pig because our table was ready. We were sat at a table inside and immediately made work of reading and translating their extensive menu of share plates.
The Chorizo Stuffed Olives, Whipped Feta Dip, and Pork Belly Rillon looked best to us. They brought each dish out separately, which made for optimal enjoyment. We started with the feta, which was served with thick slices of delicious bread. The feta had cucumbers and peppers brunoise on top and was so tasty. For me, there is literally nothing better than cheese and bread so of course I loved this dish. Next came the olives, which were a little too salty for me, but my boyfriend very much enjoyed them. Finally, the Pork Belly Rillons, which were the perfect mixture of crispy and melt in your mouth. I only wish the serving was bigger.
After we finished the decadent dinner, we walked the few blocks across the river and walked down the steps to the River Walk. The brightly lit river-adjacent sidewalk was vibrant and teeming with the after-dinner crowd. We walked down a-ways and doubled back to pop into The Hideout for a beer.

There was an extravagant process to making it that ended with lighting the garnish on fire with a blowtorch. It was a hefty portion of booze worthy of two cocktails and priced accordingly. The bar was crowded, but not uncomfortably so. The bartenders were very attentive and continued to craft creative cocktails without the pretension of other “mixologists”. We spent a good amount of time enjoying the cozy atmosphere of The Broken Shaker before retiring to our room for the night.

Part of the beauty of a staycation is that every new thing that you discover and enjoy is easily accessible for revisiting. And I plan to go back to Café Integral often, specifically for the Avocado Smash.
Before we checked out, I wanted to explore the basement of the hotel, which is where the guest laundry and kitchen was located. The kitchen was brightly lit and happily buzzing with a few other guests preparing their meals. In addition to these in house amenities, The Freehand offers an activity calendar for their guests including workouts, walking tours, and other special events much like the pop-up gallery my friend was featured in.
We left the hotel at noon, after walking around and popping into a few shops in the area. We walked the two miles back to our apartment, across the river and over the line that separates blissful staycations and real life.

