The Five Best Wintertime Activities in Chicago

The Five Best Wintertime Activities in Chicago

The days are definitely shorter, the air is getting frostier, and everywhere it is clear: winter time has truly arrived here in Chicago. While some may prefer to hole up and have a cozy, indoor winter, opting for hibernation over adventures, that is certainly not the only route available. 

There are plenty of fun, exciting activities to try in Chicago all winter long. From family friendly excursions to romantic wintertime date night activities, Chicago comes alive in the winter. 

So let’s take a look at five of the best wintertime activities to get up to in Chicago this year - from the traditional to the wacky, presented in no particular order. 

1. Ice Skating

There is truly no better way to enjoy the magical charm of wintertime in the middle of the big city than by gliding along the ice- or even laughing with loved ones as you fall mid-skate. Yes, that’s right: wintertime in Chicago means ice skating season is in full swing. This is one classic activity that hits all the marks: perfect for a fun first date, a sweet family outing, or just a get together with a group of friends, ice skating offers a beautiful way to celebrate the season. 

And Chicago has no shortage of options when it comes to ice skating rinks, either. In Hyde Park, Midway Plaisance Ice Rink offers special seasonal events, lessons, ice hockey games, and other family friendly activities. It is an outdoor rink decorated with lovely twinkling lights. Fun fact: the Midway Plaisance Ice Rink currently stands in the same location where the world’s first Ferris Wheel stood during the 1893 Chicago World’s Fair. 

For an elegant, nontraditional atmosphere, you might like to try the Sky Rink at The Peninsula Hotel. Located on the fourth floor outdoor terrace of the hotel, skating at the Sky Rink means gliding along above Michigan Avenue in the heart of downtown Chicago. Take a break from the ice to munch on warm beignets and hot mulled cider as you watch passersby traverse the city streets four floors below. 

2. Winterland at Gallagher Way

Even our beloved local icon, Wrigley Field, undergoes a wintertime transformation. Particularly good for families, Winterland at Gallagher Way is a true winter wonderland. Offering everything from an 8000 square foot ice skating rink to special performances and holiday shopping, Winterland at Gallagher Way is a must for anyone seeking to embrace the festive holiday spirit. The Christkindlmarket offers unique handicrafts and specialty items, in keeping with the traditional German Christmas markets from the 1800s. Santa Claus makes regular appearances here, and there is even a craft area with special hands-on workshops that provide you and your kids materials for making wreaths and snowflake decorations. 

Winterland at Gallagher Way also hosts regular film screenings of classic holiday movies, so you can take a break from watching whichever Christmas stories are shown on repeat on your local cable TV stations and enjoy a classic hit in the company of friends, family, and strangers alike. In addition, Winterland at Gallagher Way offers special Hannukah celebrations, ice bumper cars, seasonal specialties at Hotel Zachary, and more. 

3. Cocktails and Curling

Sometimes when the weather outside is frightful, the best way to stay warm is to enjoy some specialty seasonal cocktails. The fifth floor rooftop bar at the Gwen Hotel offers a unique take on the wintertime bar. There, amidst outdoor fire pits, guests can stay cozy, taste the seasonal cocktails and food offerings, and even learn how to curl! The rooftop bar features a special iceless curling rink, so bar patrons can sip the bar’s signature curling cocktail as they learn to play this classic wintertime game. 

For curling fans who want to try out the rinks at every bar in town, Kaiser Tiger also offers outdoor curling rinks throughout the winter. Infrared heaters are spaced throughout the outdoor beer garden and you can try out seasonal cocktails from their extensive menu, featuring their tasty (and boozy) hot chocolates. 

4. Get To Know Some Winter Animals - and Dazzling Lights

Animal enthusiasts, rejoice! The wonderful Lincoln Park Zoo remains open all year round, even on Christmas and New Year’s Day. So during the coldest months of the year, you can take a break from the chilly outdoors by exploring the animal houses, aviary, and reptile room. 

Watch tropical jungle animals romping around and remember how summer feels. Then get reacquainted with some animals for whom winter is as natural as anything: polar bears, penguins, snow monkeys, and more. The zoo is free for all visitors, making it a great, low pressure outing for families- or romance. 

During the wintertime, through early January, the zoo will come alive with lights! Zoolights is a special wintertime celebration; a festive light display that features literally millions of LED lights. Stop by for a cheerful, breathtaking experience right in the heart of the city, including new light shows and an 18 foot tall holiday tree. 

5. Warm Up With Hot Chocolate

Rife with nostalgic sweetness, nothing beats a steaming cup of hot cocoa on a cold blustery day. Chicago has countless restaurants and cafes that offer a truly delightful cup of cocoa. Try the Mexican hot chocolate at Kristoffer’s Cafe and Bakery for a true pick me up: not just chocolate with some extra spice, this wintertime treat also comes with a shot of local espresso. 

At Italian restaurant and Argentine bakery Piccolo Mondo, you can try the submarino, a specialty with a DIY component- provided with a steaming cup of milk, you stir the bar of extra dark chocolate in yourself, watching it melt. Don’t forget to lick the spoon! For a truly decadent wintertime indulgence, try the exquisite drinking chocolate at Katherine Anne Confections- the rich, European-style drinking chocolate was named one of the best 15 in the United States! 

If you want a hot chocolate that provides more than just a drink, head to BomboBar. Their hot chocolate menu includes over-the-top creations, like the Cookie Crumble, with mini bombolini, caramel custard, m and m’s, oreos, brownie bits, cookie dough, and more. You can also spike your hot chocolate with a selection of special boozy holiday drinks, like Jameson’s, Fireball, and Bailey’s. 

Have A Happy Winter!

Wintertime is the perfect season to get outside, go exploring, try new things, and make lasting memories with loved ones. Check out all the wonderful activities Chicago has to offer this winter season. 

There is no better way to embrace the festive celebratory nature of winter in the city than to get out there and take advantage of all the lovely activities that pop up throughout the winter season. Glide on the ice, check out the lights, sip some special cocktails and hot beverages, learn a new sport, and spend time with your partner, family, and friends in The Windy City this winter season.

Written by Anthony Moretti

Let's Connect

We are strategy and results-oriented. Work with us to achieve your real estate goals with less friction and the best possible outcome.
Follow Us