As a Chicago winter alumnus it’s more about the socks than the shoes. The shoes/boots need to do well against repelling water/snow, but even the best boots aren’t going to do double duty on warmth. Invest in some good wool socks (darn toughs for example). I’ve worn similar boots to the LL beans with good wool socks for hours in sub zero wisconsin and been fine. Without the socks I’d have been done in under and hour. Just my thoughts for what they are worth.