I've had my driveway repaved several times over the years. It's always been done in late spring or early summer. Maybe that's because the tax return comes at that time. Call a paving company, they'll let you know the best time.

I'm an office manager for an asphalt paving company and the best time to pave your drive is when you want it done. We're suburban, northwest of Chicago, so our work is seasonal. We pave mid April through December, weather permitting and asphalt plants open. When you say "repaved" are you going to have it all pulled out and new asphalt put over your existing stone or do a full depth with stone and asphalt new or just a resurface (primed and then asphalt put over your existing asphalt)? A simple remove and replace, using your stone, won't have any settling effect and neither will a resurface. A full depth remove and replace will settle in time. All stone settles so eventually the asphalt will crack in places. This is a normal thing due to the expansion of the ground during the winter and summer months. A hot, dry summer is worse on them than winter.

Jan