This place has covenants?
Personally, I think HWY 20 would be a more likely escape route for refugees leaving Chicago than say I90. Not those two specifically, just that any small highway leaving Chicago would be a better route than the Interstate corridors. Small highways would still be easy to follow, offer a pretty straight line of travel, and would have lots of scavenging opportunities. If I were desperately leaving Chicago, I would not take the Interstate system. Maybe as a first step, go to where you think the majority of the people you think will be a problem are, then try to decide if you were them, where would you go? How would you scavenge and where would you start? Where are the first easy pickings?
Your defensive needs would also depend on where you are. Elgin is a lot different than Carpentersville, IMO, even though they aren't that far apart.
Anyway, if your beginning homestead is in a suburb with covenants and an association *shudder* then there isn't much you can do right now. If I had to stay there, I would plan on getting to know the neighbors, and having a couple bigger dogs, and try to pick some places with the best view of the property, places you could sit and watch out for problems. 10 acres is big, but doable. Sucks though, room for growing food and having chickens and rabbits, but hard to defend because of the location and current rules.
It would take a real horrific, long term emergency to send hordes out combing the countryside, I think. Me, I would focus on food stores and sustainability, and armed defense, before worrying about ****y traps, or fencing. There really isn't a fence good at keeping out people, not when they access to tools and time. I wouldn't be against a nice hedge to hide the property from view. No need to have the garden on display.