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House flipping is legal in IL as well as WI and there are no laws prohibiting it. However, if you are going to engage in the business of selling houses after you fix them, you will have to obtain a real estate license
if you want to sell without any other agent involved.
You can buy homes in bulk, but would need a contractor
's license to make the repairs or would need to hire licensed contractors to do the work. You can also sell without doing any rehab on the house. This is legal in both WI and IL.
All of what you want to do above is legal in IL and WI, but selling of houses does require a real estate license and if you are going to get into doing this it should not be very difficult for you to obtain your real estate license.
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