That's awesome that you are thinking of getting started, definitely do it!! As I am sure you have heard, house hacking is an amazing way to start and there are a few good areas in Chicago that work well.
First for Jobs- Check with GC Realty, @Mark Ainley would be amazing to learn from (also hosts one of the events below with @Tom Shallcross), here is the link for their jobs:
https://www.gcrealtyinc.com/ca...
My guess is you may be too early on in being able to get something under contract immediately without having an income history but it's not too early to start connecting with lenders, investors, and realtors, and learning about which areas and types of deals would make sense for you.
My recommendation is to connect with local investors at meetups, get to know a few people, and get a feel for what they are doing and in what areas. Here are a few places to connect, there are 3 awesome meetups coming up:
- Chicago West Suburban Real Estate Investors Meetup https://www.eventbrite.com/e/f...
- Straight Up Chicago Investor Networking Event: https://www.straightupchicagoi...
- Chicago RE Investor Meetup with @Jonathan Klemm https://www.biggerpockets.com/...
Connect with a local realtor and lender that can help you strategize and see what makes sense for your situation. I use @John Warren as my realtor and couldn't ask for a better team, you'll learn a ton just from one conversation (I certainly have over the last couple years). I use @Zack Karp as my lender and they rock as well, smart, creative, always willing to help, and very professional in loan processing.
If you get set up with a couple of good connections then everything in the process will be smooth from selecting an area and strategy up to closing on your first deal. Good luck!