Okay, here's my advice: you said your max rent is $ 750, and you'll need the place to be dog friendly. You should be able to find a one-unit place in one of these neighborhoods between 400 and 650 that is dog friendly: Mexicantown, Midtown, North Corktown, Woodbridge or maybe Corktown [[little more expensive these days). Or, get a roommate and split a two bedroom for like $ 700 [[you'd save some dough - just a though). Ditch the parking garage in the New Center [[maybe your company will even give you a parking reimbursement). Instead, Start paying for a monthly parking space with one of the lots downtown; that should cost you about 100 bucks a month. Now, you're not tied to being near this parking garage - just a thought