@Leah T. Hi Leah, Great question. There are multiple ways at going about it. You could acquire an FHA Loan which is great for first time home buyers and also if you don't have the traditional 20% down payment. There are also programs in various states that will grant you down payment help. I know here in Maryland they have various first time home buyer programs that will grant up to $5000 for a down payment. Maybe Chicago has the same thing. Just have to do some digging. if you plan on House hacking your first investment which is not a bad idea at all depending on your situation, You can put down as little as 3.5% for the FHA. If the numbers add up, you would potentially live for free with some cash as well. The great thing is once you move out of the units you were living in. You could then rent that unit out and increase your cash flow. The great thing about the FHA loan is that you can use it more then once. Either way I would say depending on your situation in which I don't know fully. Going the house hacking route is a great way to get your feet wet in the game. Along with giving you the hard knocks teaching of becoming a land lord.
Good Luck on your journey! You can do it!