Chicago Winter Activities

We’ve arrived! It’s officially winter in Chicago. I know Chicago offers a plethora of things to do in warmer months, but don’t count winter out! You’d be surprised at all the winter fun available for all in Chicago and surrounding areas.

Just walking around after a fresh snow is enough to make you fall in love with this winter wonderland, also known as Chicago, but if you want to play in it you’ll have to check out these fun sledding hills in the city.

Lincoln Park. Head to the north end by the playgrounds closer to the Diversey side and you’ll find several hills ranging from small to large. I would go early because by mid-afternoon it gets crowded and you have people sledding in all different directions – which always makes me nervous for safety concerns of kids running into each other.

Horner Park. This park is off Irving Park and California and also has some great sledding hills for the city.

If you’re tired of being cooped up inside, you can venture out to some of the creative spaces Chicago restaurants have made available due to Covid and keep you warm while dining outside.

Dine-in an Igloo! We have dined in several igloos this past month and one of our favorites was at Barcocina. Kids are free, adults are $100 per person – but that comes with a 2-hour reservation, three food selections, two drink selections, a heater, couches, blankets, and a wireless Bluetooth speaker to play your own music. We went with two adult couples for a date night and had basically all you can eat tacos, elotes, margaritas, and sangria! Highly recommend them. So many places are offering safe eating experiences and what better way to support our local Chicago eateries. A good resource to check out all the igloo/outdoor dining options is on Timeout Chicago.

Old Grounds Social / Lincoln Park They have a bottomless brunch on their winterized wonderland patio that runs about $50 a person. Someone book and invite me! They had me at “bottomless mimosas”.

Maggie Daley Ice Ribbon. We love the ribbon and it’s one of our favorite winter activities in Chicago. You can’t beat the backdrop either! Experience “alpine in the city” skating down a quarter-mile winding ribbon of ice that curves up and down around a 40-foot climbing wall with the city’s stunning skyline in the backdrop. It’s a must for your winter bucket list. Reservations cost $5 for those who have skates and $16 for those who rent. (via Secret Chicago) Image via TimeOut Chicago.

If you want to venture outside of the city, here are some places within a couple of hours or less of a drive from Chicago.

The Forge at Lemont Quarries. This is an adventure park just 20 miles from downtown Chicago. They feature activities like ziplines, climbing walls, and towering ropes. Be sure to bundle up depending on the temps and some activities are only available weather permitting. Plus, The Forge also has a 3,600-square-foot ice skating rink. Score! Check their website for pricing and details.

Wilmont Mountain. Just about an hour from Chicago, Wilmont Mountain offers skiing, tubing, and more winter fun for the whole family. It’s also a great spot if you have beginner skiers in your group.

Wilmont has almost 120 skiable acres, 25 trails, 7 lifts, 2 surface conveyor lifts, and 4 progression terrain parks with a double high-speed rope tow, there is enough terrain to challenge experts to beginners, day or night.

They also have snow tubing! The image above via Yelp. For those who are not up to skiing or snowboarding, there is the tubing area which has 22 lanes and 2 surface conveyor lifts to take you back to the top.

They offer lessons and ski school for the littles, too. You can make a day out of it or stay at the resort and make a weekend out of it.

Starved Rock. Our family was here in the Fall and it’s one of my favorite places to go. Sometimes you need wide-open spaces and fresh air. It’s a little over two hours of a drive from downtown Chicago. There are almost a dozen hiking trails and you’re surrounded by the grand beauty of nature. I’ve read it’s even more beautiful in winter with layers of white snow on the ground and ice sculptures hanging from all the caverns. Those sites alone would be enough to garner a day trip out to Starved Rock.

Ice Castles at Lake Geneva Per their website, Ice Castles is an award-winning frozen attraction located in four cities across North America. The experience is built using hundreds of thousands of icicles hand-placed by professional ice artists. The castles include breathtaking LED-lit sculptures, frozen thrones, ice-carved tunnels, slides, fountains, and much more. Ours is located just over the border in Wisconsin.

Tickets go on sale soon as the castles open up mid January. If you want to make a weekend of it, some resorts are offering packages that include the Ice Castles, tubing, and/or ski packages as well. We will definitely be checking out this phenomenon this winter!

If you have any favorite Chicago winter activities be sure to share them below or with me on social!

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Holly Rust is a native Texan currently living in the great city of Chicago with her husband and two sons. Aside from chasing around two lunatic boys all day, she is a writer, author, and runs a global skin care business. Her blog was featured on The TODAY Show’s List of Funniest Parents on Facebook. You can find her work on HuffPo, Good Housekeeping, Town & Country, Scary Mommy, Dot Complicated, TODAY and many more. You can also find her essays published in several anthologies. Follow her random thoughts on Facebook and Instagram – but no judging.

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