Nikki, what part of Chicago are you in? I'm thinking as the weather cools down maybe you could load Bailey up (and BF too of course!) get a map of local sales, something good to drink for the 3 of you and have a fun day...look for the obvious things -like x-pens and strollers,but look at things in a different way too. I've picked up baby items that work great for my furkids,like toys,blankets...stuff like that.
Mine actually get all excited in the fall when we go "garage sale-ing"