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I lived in Chicago for 4 years when I was in University. I worked outdoor during winters, Chicago is pretty cold place almost like Toronto. I was young then but still here are my tips.

1. Wear a cap which can also cover the ears.
2. Thermal under-clothing is very effective to keep you warm.
3. It is wise to wear gloves and it is recommended to wear snow boots if you are required to walk outdoor for extended periods.

Everything thing said and done extreme cold climates are very tough to live in, Chicago used to have limited sunshine during the winter season which used to depress me.

Unfortunately, where I currently live the trade off in climate would be worth the enhanced security. I just hope that I would be able to get a decent income going as money has a funny way of making the climate much more tolerable.
 
DR Who said:
I lived in Chicago for 4 years when I was in University. I worked outdoor during winters, Chicago is pretty cold place almost like Toronto. I was young then but still here are my tips.

1. Wear a cap which can also cover the ears.
2. Thermal under-clothing is very effective to keep you warm.
3. It is wise to wear gloves and it is recommended to wear snow boots if you are required to walk outdoor for extended periods.

Everything thing said and done extreme cold climates are very tough to live in, Chicago used to have limited sunshine during the winter season which used to depress me.

Unfortunately, where I currently live the trade off in climate would be worth the enhanced security. I just hope that I would be able to get a decent income going as money has a funny way of making the climate much more tolerable.

Thanks for your Tips