There is an area in IL that has the largest truck driver need in most all of the US. They have billboards up along the road that read "Owner Operators! Make $300k a year with us! We need you today!" Joliet, IL. Also Elwood, IL. Every major warehouse (think Amazon) has a million square foot+ building there & need to ship out goods right now. Do a google earth search on Centerpoint Rd in Elwood. It is truck driver heaven.
Now that is about 45 minutes out of Chicago. But (like someone said earlier) its not in the City, its pretty far away. What does that area have other than the great pay for a hard job? Average Home price is $160k. Really nice homes are $200k. Big yard. Pool (that you can only use 5 months of the year). Property taxes are the worst tho. A $200k home will be $3000-$5000 a year depending on zip code. But... Plenty of good schools.
Midwest people are generally good folk. The politics are not ideal in the big City, but can be dealt with further out. There are only two seasons, summer & winter. But bring your family (you have a great looking fam) up with Midwestern values and make a TON of money driving, then leave and take your money with you once the kids are ready to go out on their own. Crime in a city like Cole City,IL (close to truck haven) is nearly none. There are drugs looking for your kids everywhere, but at least there are not zombies in the streets of these regular MidWest locations.
Right now the truck driver pay there is strong. Take advantage - then go to the next hot spot when the mood strikes you again. You are young and have saleable youth that is valuable to many companies.
