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My usual schpeel on winter cycling below:

Keeping your bike in shape:

• Rust-proof your frame/fork if you ride steel. Salted, slushy streets are bad news for damn near everything on your bike.
  
• Get some lube designed for wet/gritty conditions. Again, salty slushy streets; your chain'll be going through more than it usually does in the winter.
  
• Fenders are awesome. You already have some, but to anyone else who's reading this and doesn't, get at least a rear fender. SKS makes a few cheap, solid seatpost-mount ones for $14 or so for road and mountain bikes.
  
• Tyres: This one's optional, really. Knobbies help when the streets are so oversalted that it's like gravel, but if you've got wide tyres then you'll be fine on slicks. My housemate's done winter on his 23s, came out of it fine. Obviously, MTBs have a tire width advantage here.
  
  Keeping yourself warm:
  
  
• Base layers are great. You don't have to go all-out on these, just get something snug and comfortable. Something like this will do you just fine, and may even be overkill on some days. I used MEC's T1 and T2 tights throughout last year, and had no trouble. Was even pretty toasty on most days!
  
• Softshells are also great. I'm a fan of the Gore Bike Wear stuff, specifically their Phantom jacket. I realize last winter was pretty mild, but I only donned this and a simple long-sleeved shirt (usually polyester, occasionally cotton) and much like my bottom half, was nicely toasty. Shameless plug: I'm selling a grey medium-sized Phantom for $80 (got it as a gift but only wore it for a week in the fall, bought a small instead)
  
• Tights are nice, but optional. Any kind of waterproof/resistant pants should do you alright. Look into Craft brand stuff, or swing by REI if you're near one. They've got plenty of cheap stuff.
  
• Gaiters/shoe covers/plastic bags: Whatever keeps your feet dry. Wet shoes/socks are, if not the start to getting frostbitten feet, at least pretty damn annoying.
  
• Wool socks: Because your feet are going to get cold, possibly wet, and wool both insulates nicely and dries quickly. On that note, keep a spare pair of socks on you during your commute. Nothing sucks like biking to work/school, getting wet feet, and having to deal with it all day.
  
• Gloves: If you're getting some simple softshell gloves, go one size larger than your usual; wear some cheap mittens under those, and voila, instant double-layered hands on the cheap. If it gets really frigid, throw some wool mitts over that combo and you're set for anything. Alternatively to all this, just get some gloves meant for skiing/snowboarding. It's easy to keep most of your body warm since it's moving all the time, but your hands are just sitting on the bars getting hit by wind. Easy for them to get chilly.
  
• Shoes! Riding on platform pedals? Salomon makes some damn nice waterproof/resistant shoes/boots. Riding clipless? Five Ten makes some great, heavy-duty shoes that have some decent weatherproofing thanks to the "action leather" they're made wtih. Check out their Cyclones.
  
  Tips:
  
  
• Remember, you've got to dress for both being active and not. Sometimes you'll be pedaling hard, sometimes you'll be pedaling lightly or walking around. Find a good balance in layers that won't have you being too hot with the former, or too cold with the latter.
  
• Lights are always a good investment, be it winter or any other season. Winter especially, since the sun's not out for quite as long. Keep visible. For a powerful front light, get a flashlight and a handlebar mount. I use the Fenix TK-21 and this cheap mount. for commuting, touring, mountain biking, you name it. And then you've got yourself a flashlight off the bike too!
  
• "Cotton kills" is a bit of an overdramatic statement, but cotton's generally good to avoid. It doesn't dry particularly well, meaning if you get wet, you'll be wet for a while. Wet + cold is a nasty combination, too. Polyester and wool stuff is nice.
  
• Head to Village Cycle Center in Old Town. They know their stuff and they'll talk winter biking (or any biking, really) with you for however long you like. Good folks.

Possibly repeating some advice since I'm late to this party, but..Shoes: Also a lady and I stumbled upon the Keds Scout line last year and they have turned out to be great winter biking shoes. They are water resistant, don't let wind through, but are slim enough that they still fit in my pedal cages and aren't so clumsy that they make me feel like I'm pedaling my bike with inch thick stumps like snow boots do. I'm on my second pair of the Scout Chukka Splash which is mostly unlined but I think they offer other versions that are geared to be more winter-y and have thicker lining. I have worn them with thick socks over the last two weeks when temps have gotten pretty low and been fine. The only day I had cold toes was Wednesday when the "feels like" was in the negatives in the morning, but it wasn't terrible. They're not full plastic waterproof to where you could stand submerged puddle for 10 minutes without worry, but the water resistance is good enough for normal snowy conditions. Bonus: depending on your work environment and personal style choices, you can possibly wear them to work and not have to carry extra shoes.

Gloves: I listened to the crowd and shelled out for Pearl Izumi lobster gloves.. they're great for middle temps down to like 20ish and keeping dry but fail once it really gets cold. The sizing is men's so even the XS is big on me which is irritating for the cost. If you have ski mittens already, use those. If you have no good gloves and plan to spend money, I'd recommend ski mittens over the lobster gloves - I have these Dakine mittens in size small and they are fantastic for very cold days, plus I really love the liner gloves they come with for fall riding when it starts to get cold.

I have no special bike outfitting for winter other than fenders. My slick road tires have kept me upright this week despite the ice and such but I've definitely had some dicey moments. If in doubt, take the lane - don't ride on the edge near the BL where cars are encouraged to pass you close because there's * almost * enough room and you risk being surprised by ice that sticks out of the bike lane or getting pushed over, ride roughly in the right car tire tracks.

Face: If you don't already wear glasses and don't want to wear goggles, buy some cheap "non-prescription" clear lens glasses on amazon. I replaced my silly scratched up shop glasses with non-prescription glasses this year and have been happy with them so far, especially on days like Monday when it's snowing tiny ice bullets and I otherwise was unable to keep my eyes open. Fogging is a problem though.

Neck: Fleece "buffs" or neck gaiters are a must. Keeps your sensitive neck parts warm even if your core warms up and you want to unzip your jacket, and breathing through something while covering your mouth and nose is very helpful for keeping your lungs working in the cold dry winter.

Edit: If you have long hair and it is snowing, tuck it in to your jacket. Dealing with a matted, wet, frozen ponytail end at work is annoying.

Definitely yes to the adding lights this time of year! I bought some cheap ones to give out to commuters that I see that don't have any. I have a Cygolite Metro that I'm fond of for personal use, love the USB rechargeable ones.

I haven't tried bar mitts, but I like lobster gloves for winter riding - mine also have a liner that I wear underneath the gloves. They seem to work pretty well down to single digits.

I'm also a big fan of this: https://www.amazon.com/gp/product/B0018BGFF4 with a thin hat, I have a cover for my helmet too.

My winter commuter is an internal gear hub & brakes 3 speed, also less to be exposed to the elements.

After trying heavy gloves, lobster gloves, and a variety of layering I have to say I feel stupid for not doing bar mitts style pogies sooner. Wasn't sure if I'd like them so even got some off brand ones for $23 and even those are great.

Days in the 20s have required no gloves and this morning I had to open the vents to keep my hands from getting too warm. Amazing!

These are the ones I got, haven't had them long enough to couch for durability but performance has been great so far.

ODIER Bike Handlebar Mitts Cyclist Pogies Mittens for Winter Thermal Cover for Handlebar Keep Hands Warm 1 Pair (Bar-Straight) https://www.amazon.com/dp/B077SY7J6F/ref=cm_sw_r_sms_apa_i_jrZ0DbQREJW3J

I have a silver 59cm Windsor Wellington 3, bought this summer, less than 100 miles on it, with new Shimano A530 pedals (SPD on one side, platform on the other)

http://www.bikesdirect.com/products/windsor/wellington3-xv.htm
https://www.amazon.com/gp/product/B001MZ2AGO

It was inspected by Bike Lane in Logan Square after assembly, everything's in good shape.

I just prefer my old bike and I still ride it exclusively, so this one is just taking up space. Make me an offer if you're interested. Thanks!

I hear kool stops are pretty awesome. I know Comrades sells them and Amazon has them listed for roughly the same cost as those first ones.

https://www.amazon.com/Kool-Stop-Compound-Mountain-Linear-Threaded/dp/B001CLSWKQ

I have one of these on all of my bikes! Best $20 I've spent. I don't use it unless I have to.

https://www.amazon.com/gp/product/B000ACAMJC/ref=oh_aui_detailpage_o03_s00?ie=UTF8&psc=1

I run this on my rear and like the results. Only used last winter, worked well in the slush, can run at lower PSI as well (at least on my rim)
https://www.amazon.com/gp/product/B00C4Z0JW8/ref=oh_aui_search_detailpage?ie=UTF8&psc=1

And this one on my front:
https://www.amazon.com/gp/product/B0025U2NX0/ref=oh_aui_search_detailpage?ie=UTF8&psc=1

Weird circumstance on how I have two different ones, but seems to work out well since the "beefier" one is on my rear where my weight is mostly.

http://www.amazon.com/Delta-TD9130-Hublox-Security-Skewers/dp/B000MIVN3S is an example. They make them for seatposts as well. Basically skewers that can only be open with a special key.

For a road bike I currently run the conti grand prix 4 seasons.

I finally bought a bike rack for my steel frame Scwhinn. Does anyone have any panniers / baskets / boxes they recommend? Or for sale? I'll be doing daily commutes and occasional 'touring' rides.

Chicago has so much cycling history. A local cyclist, Chris McAuliffe, who is on xXx Racing published a great book for anyone interested in more.

waterproof breathable shell +

waterproof hiking boots +

big platform pedals like these:

http://www.amazon.com/MKS-Lambda-Pedals-16-Silver/dp/B001GSQVEE

1. You shouldn't be on LSD. Ride the Lakefront Trail as sheatarco mentioned.
   
   
2. I ride south on the bike path all the time. No issues. I use cheep Sunlite Bike Tubes. Maybe it's your tires?
   
   Hope this helps.

Crane Bell Suzue Brass Lever. Loud. Pure Tone. There should be a picture of this bell next to the dictionary definition of "bicycle bell."

Also, why is this lock so cheap?

Bar mitts beat any gloves you're gonna get.

I bought these last winter and they were toasty af and still let me have some dexterity.

I have been using this top and this pant for a couple years. I don't know about shoe covers, I wear old sneakers to ride in the rain and don't care if they get wet.

Dual lens snow goggles plus this thing that I've dubbed (sic) "the scraf" that you put on before your helmet and has... exhaust vents out the front.

I'd go with gatorskins - http://www.amazon.com/Continental-Gatorskin-Bicycle-700x23-Folding/dp/B001UL5JNG/ref=sr_1_3?s=sporting-goods&ie=UTF8&qid=1377714003&sr=1-3&keywords=gatorskin

Treads serve no technical purpose for commuting.

Edit: Also, it's all about performance.