To say nothing of flying over the DPRK first! And I don't think that it's illegal from from the Russian side to overfly their territory, but most countries these days choose to restrict aircraft registered with them from doing so. In other words, I don't think the Russians will send MIGs to intercept you, but you'd probably hear from the FAA on landing.Part of that dotted line goes over Russian airspace (I think the part above the "U" in UPS is Russian soil) and definitely the weird shaped peninsula thingie in the middle is Russia. Would that even be legal to fly over Russian soil?