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Ask yourself how many miles a week you are currently running and let that help determine a race. If you already run a lot of miles a week with long runs in two digits, then you could train for one no sooner than 3-4 months. That would be pushing it for Chicago (which by the way would be a fun one). Choose one that is large with a festive atmosphere. It is a ways away, but the Rock 'N Roll is a blast. Good luck and happy training.
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