Download the B4UFly app which will show you on a map where you can fly without notifying an airport.
The areas in orange are where you just have to notify the airport before flying. However, I’d stay away from the one that says C on it until you are more confident.
The one that says C is the airspace around major airports. Funny it doesn’t show O’Hares class C but stay away from Midway and O’Hare for now.
If there any nearby RC Clubs in your area you can join there and fly within there field area. You might need to join the AMA (Aircraft Modelers Association) which also provides great insurance for any liability.
Another thing I found out is that you can insure your drone under your homeowners insurance policy. I have State Farm coverage and spoke to my agent, he included my drone under a Personal Property section. I am now covered for theft, fire, loss of any kind (if my drone flies away, drops into the lake or I accidentally crash it into a tree) for its full replacement value with zero deductible! All for $60 per year, or $5/mo which is great. Keep in mind this is only drone replacement insurance, not liability. But spending $60 is a lot easier to swallow than losing $1,500 if you're a noob.