I also live in Chicago and the winters here are rough. I had these http://www.llbean.com/webapp/wcs/stores/servlet/CategoryDisplay?page=llbean-boots&categoryId=35487&storeId=1&catalogId=1&langId=-1&parentCategory=502770&cat4=505543&shop_method=pp&feat=592-sub1&np=Y

Best boots Ive owned warm and very comfortable. Also Ive had them for about 3 years and no problem, worth every penny.

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as a Canadian city dweller, I've found these to be the most useful. I have a pair of uptowner x now but have owned a pair of villagers in the past.

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I have two different pairs of boots, for Snow, mud, etc. Having been in Southern Cal, (Spent a lot of time in the mountains, and TX, where the Mud gets just as bad as snow, both types are very useful and comfortable.

I have a pair of Asolo Fugitive GTX Hikers, (http://www.rei.com/product/706762), which are very comfortable, well insulated, great tread, and completely waterproof. These are the lighter of the pair, and they look pretty cool too.

I also have a pair of Red Wing Boots. They have a lot of different styles, even some that you could pull off with business casual. Most have GoreTex lining making them waterproof, but the pair that I got are called the Pecos, (http://www.redwingshoes.com/productdetails.aspx?prodid=1170). They are 11 inch uppers, no laces, with steel toe, and you can choose from a variety of soles from those suited for slick shop floors or heavy tread more suited for, in this case, Snow. These are also completely waterproof, and insulated very well.

With either pair of these boots and a good pair of wool socks underneath, and your feet will never know it is snowy, cold or wet.

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Best all around boots: Bean Boots
These all-weather boots will keep your feet both warm and dry. They're insulated and waterproof, which are the two things you want in winter boots. Great value at $94.

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I love the Northface Arctic Pullons. They don't have laces and just pull on, are comfortable as anything I've worn and are completely waterproof. I bought them when we got a puppy a few years back and had to take her out in sub-zero deep snow conditions in northern Illinois. Never let me down. I tend to wear them regularly because it takes seconds to get them on and off.

Northface Arctic Pullons

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Go with Keen Growlers. http://www.theshoemart.com/keen-mens-growler-black-olive-rust/pvc-kee-mxsbs-1220-boru_kee_m_growler.html

They are fantastic for wide feet, have wonderful odour eating properties, and protect your toes ! Keen make some amazing footwear. I can't stop buying them.

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Sorry, missed the link. "as a Canadian city dweller, I've found these to be the most useful. I have a pair of uptowner x now but have owned a pair of villagers in the past."

Neo Overshoes http://www.overshoe.com/recreational/

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Keen Growler's are hands down the best. I go to school in Minnesota and wear these when it is cold outside, in the snow, in the rain, in the mud, in the slush, everywhere and my feet stay completely dry.

If you are going to be out for long periods of time in the snow and what not, something more rugged might be a little more. Keen's Summit County would probably be your best bet.

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ECCO Track Gore-Tex
These won't look out place with jeans or slacks. The interior ventilates really well - never too hot and the rubber cushioning sole is amazing - grips and feels like you're wearing a pair of sneakers. The leather is really resilient and the stitching is top notch. I've owned my pair of Track II High for about 3 years, wearing them from November to April pretty much exclusively. The only weak point I could tell you about is the pull strap at the back of the shoe ripped almost right away - I had them replaced right away. I've own(ed) a number of boots over the years, keen, docs, tims, asolo, lots of different stuff from casual to hikers and some mudkickers, and this is the a serious boot you can wear all the time.

PS
One of the things that initially attracted me to ecco is that they seem to fit identical no matter what type of shoe you're buying.

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The OG: Sorel Caribou boot in color "Buff." As good for sloppily trudging thru city slush as for strapping into some snowshoes and hitting the trail. I picked up mine at the local REI a few years ago and they won't be replaced any time soon. http://www.sorel.com/Product.aspx?top=1&cat=120&prod=49

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Having shoveled plenty of snow up here in New York over the years I know a little about snow boots. The ones I like the best are the shearling lined LL Bean Boots available at http://www.llbean.com/webapp/wcs/stores/servlet/CategoryDisplay?categoryId=43351&storeId=1&catalogId=1&langId=-1&parentCategory=502966&feat=502966-tn&cat4=505557 . I like them because they are warm and no wetness ever gets in. And they aren't cumbersome so they can be worn all day. You can also get the non-shearling lined boots at the same website which provide for ample room to wear as many as 3 pairs of socks making them very comfortable as well.

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Columbia

Why would you write product name?

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