3142 W Diversey Ave
Is there anything more "Chicago" than a greystone? This place stretches the limit of what I consider affordable, but it IS a 2-flat - perfect for making some rental income. On top of that, it's in a HOT Logan Square location, and just a block away from the train. There will certainly be a line of potential renters! All it needs is some cosmetic updates - new floors, a kitchen refresh, etc.
2 units - one 3 bed, 2 bath and one 2 bed, 2 bath. $475k. Somebody buy this house: it's a great investment if you can swing it.
