Best Places in Chicago to Go Sledding

Sledding in the Windy City isn’t like sledding on the hill behind your neighbor’s house in your small town. You’re more than likely going to have to share, but don’t let that get you down, because no one can frown while blasting down a snow-covered hill like a young Charles Foster Kane.

Caldwell Woods

Like something that would be a side feature at a ski lodge, Caldwell Woods’ sledding hill in Oak Park isn’t anything but a sledding hill. Walk up the gated side, which will have a bit of a line if you don’t come during the off-hours, and slide down the steep but smooth bank in gleeful wintery cheer.

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Dan Ryan Woods

The sledding hill at Dan Ryan Woods is tailored for the family outing. We’re talking ample parking, no crowds, and a 200 foot hill that’s not very steep, perfect for children while still being tolerably tame for the big’uns.

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Soldier Field

When they renovated the field, they added a sledding hill, and boy is it impressive. 220 feet of chilly thrills, and if there’s one downside to sledding, it’s lugging the sled back up the hill. Soldier Field’s sledding hill is rocking a T-Bar lift. Can’t beat that.

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The Best Brownies in Chicago

The chocolate brownie was invented in Chicago during the time of the World’s Columbian Exposition by Bertha Palmer in 1893, and has since become a sweet staple of gooey goodness. You can still get the original if you stay at the Palmer House Hotel, but over a hundred years of perfecting has led us to these MostBest top three spots for getting an international favorite that started right here.

Dinkel’s Bakery

Head over to this Lakeview favorite right off the Paulina – Brown Line stop and experience some of the best brownies in town. The particularly famous one is the Brownie Torte, with a buttercream filling and chocolate ganache for the frosting, and head over on Thursdays for their four brownies for $5.99 special!

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La Estrella

While they have a slew of baked goods, all excellent in their own right, there’s something about the brownies that have people stompin’ their feet and howlin’ for more. Chocolate fudge filling with just the right helping of frosting complete with walnuts on top. It’s exceptional without exception.

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Sweet Mandy B’s

This is a world-famous bakery, so they’re obviously going to have exceptional brownies, but they don’t treat them like an added bonus, they treat them with some serious respect. The six different flavors include fudge, mint chocolate, rocky road, turtle, German chocolate, and marshmallow dream.

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Best January Festivals in Chicago

Spring, summer, and fall leave winter in the dust when it comes to the number of options for festivals, but January boasts some exceptional options that are sure to become annual traditions. Brave the cold, they’re worth it.

Sketch Comedy Festival

A local staple of the Chicago comedy scene, Stage 773 has been hosting the country’s largest and premier sketch fest, with almost 200 shows. When you consistently deliver for over ten years, you know we’ll be in attendance at least one of the ten nights ready to laugh.

When: January 7 – January 17
Where: Stage 773
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MLK Day Celebration

At the Black Ensemble Theater Cultural Center, a tribute to Martin Luther King on his day of memory features eclectic entertainment, from song and dance to poetry and music, as well as a reception with mingling, snacks, and refreshments.

When: Monday, January 18
Where: Black Ensemble Theater Cultural Center
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German Party and Winter Beer Festival

Lincoln Square, also known as Germantown, houses DANK Haus German American Cultural Center, and they have two back-to-back nights of fun. The first is a dance party and burlesque show, and the second is Winter Beer Fest, and you drink and eat delicious German beer and food at both.

When: Friday, January 29 & Saturday, January 30
Where: DANK Haus German American Cultural Center
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