1. Wear the right socks. I know its tempting to grab your regular old cotton socks, but they don't wick away moisture. Wicking socks are made of fabrics like acrylic or wool.  
2. Use two pairs of socks. Saying Chicago can get pretty cold is an understatement. If it is really cold, wear one lighter sock made of synthetic material and then a thicker wool sock over the thinner sock. Be advised that your running shoes may not fit properly with two pairs of socks. In that case, purchase a second pair of running shoes 1/2 size bigger than you normally wear.  
3. Use hand warmers in your running shoes. Put them inside your sock on top of your toes. Once your feet are warm, they can be taken out as to not overheat.  
4. Avoid puddles, slush, and snow. Use a little common sense!
5. Choose the right shoes. 

   For running in cold weather, choose a shoe with little mesh since that is where water and cold can get through.

6. Wear a hat. What do hats have to do with feet? You can lose up to 40% of your heat from your head. To keep the rest of your body warm, wear a hat.  

There are many types and brands of running shoes available. Which pair do you choose? Focus on what type of feet you have first! First, take a look at your foot. Do a fun experiment... examine your footprint by running in the sand or on paper with wet feet.

Most people fall into one of three types of feet.

Flat Feet

Do you have an arch? If not, you have flat feet. The bottom of your foot, from your toes to your heel, is flat. If you do one of the experiments above, you won't see an inward curve. So what kind of shoes do you need? A running shoe that maintains stability. Look for desciptions with the words "motion control" or "stability". Most likely you will also need orthotics.

High-arched Feet

Look to see if you have high arches. If you do the foot test, your print will curve inward, making the middle part of the foot look very skinny. People with high arches need to examine thier feet periodically since running will cause the arches to gradually fall, making the feet longer. What kind of shoes do you need? You need flexible shoes with a soft midsole that absorbs shock. Look for descriptive words such as "flexible" or "cushioned".

Neutral or Normal Feet

Your feet are not flat nor have a high arch. Your footprint will have a noticeable curve inward, but not by more than 3/4 of an inch. People will neutral feet can choose from a wide variety of running shoes but stay away from shoes that have a lot of stability or motion control.