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Welcome! 

Don't let the "cold weather" keep you from training.  I enjoyed winter running (in Peoria and Northern Utah).  Everyone is different, but it really doesn't take a lot to run year-round even in Chicago.  It's easy to overdress!  Rule of thumb is if you're comfortable in the first 5-10 minutes, you're overdressed and risk sweat-soaking your clothes before the end of the run.  

Above 50°F, it was usually just shorts and a short-sleeve t-shirt.  
40-50°F I might wear shorts or tights, long-sleeve t-shirt, and knit gloves.  
30-40°F I'd wear soft-shell pants, t-shirt, and a long-sleeve t-shirt and knit gloves.  Maybe a ball cap.  
(Or a t-shirt and soft-shell fleece)
20-30°F I'd wear tights and wind pants or heavier fleece, long-sleeve t-shirt, and heavier fleece.  I'd also switch to fleece gloves below 25°F.  I'd wear a headband, ball cap, or fleece cap.  
10-20°F I'd wear heavier fleece pants, a heavier jacket, heavier fleece gloves, fleece cap, and maybe a muffler/scarf/face cover.  
I could add additional layers for colder weather and/or windproof jacket/pants if it is windy.  I had some gear that I wouldn't wear unless it was <20°F because I'd overheat too easily.  

I ran 3-5 miles even in -4°F weather.  I ran 12 miles on a 9°F day.  During the last half of the run, my hearing got strange (like I had my head in a barrel).  When I finished and pulled off the knit hat, my sweat had frozen into ice cubes over my ears!  

I wore regular running shoes most of the time and might switch to trail shoes for light snow/ice.  Some hardcore runners will take an older pair of shoes and put sheet metal screws in the soles for traction on ice (just make sure the screws don't go all the way through the sole!)  

Biking is similar, but windproof becomes more important.  Arm warmers, knee warmers, toe covers, beanie under the helmet.  Covering the face is harder.  I'd ride my trainer staring at the back door...