Young, no experience, insurance problems

In Chicago you're going to have to learn the difference between W2 pay and 1099. 1099 will gross you more pay to begin with, but your tax burden will be much greater and you'll have no protections like unemployment and benefits like health insurance and a 401k. That's not even getting into the fact that 1099 pay in most outfits it flat out illegal.

 

1099 you may bear any liability in an accident, which can run into the millions of dollars. There are law firms that specialize in suing trucking companies and drivers and they're experts at it.

OK, you got your cdl in "half the time & a quarter of the $$", but still unemployed.
Try Craigslist and maybe you'll find what you want. Make lots of phone calls and leave lots of messages.

 

I thought you wanted legal. Anyway, if you want good 1099 pay you're going to want to look for 70cpm and up to compare to current well paying W2 companies paying 50+cpm.

 

I'm not trying to tell you what to do; just advising on some pitfalls, expensive pitfalls, you may encounter.
.70 cents-per-mile isn't much money when you have to make your own deductions for taxes, such as federal, state, social security, workers compensation, plus no medical or retirement benefits. Legally, you must file taxes every 3 months, but many drivers ignore that and still file once a year.

 

You can make average $1500 weekly on W-2 working for FFE (Frozen Food Express) running teams doing LTL. You'll have a full benefits package there also. They have a terminal in Chicago.
@TravR1 can give you tips on FFE; he works there.

 

Look for white Volvos with Russian names