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Going to Chicago in February - How screwed am I?
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Pretty standard stuff imo, keep your extremities covered; gloves, hat, waterproof boots, and a nice jacket. You'll be fine imo. If you're driving and there's snow on the ground, just take it nice and slow. Accelerate slower than you normally would. Start breaking earlier than you normally would. And plan for travel to take longer when it's snowing.
How likely is it for any bad weather to effect the public transit options?
Maybe some delays, but we're used to snow. There's pretty solid infrastructure for dealing with snow. We have plenty of plows and salt trucks, people generally know how to drive in it, you should be fine taking public transit as long as you bake in a little extra time.