AHHHH thrifting. A shopaholics best friend. Chicago has some really great places to shop vintage and second hand but a lot of them I find to be over crowded with hipsters and merchandise that looks and is priced like it could be from Urban Outfitters. I have the best luck at thrift stores that are more of a warehouse FULL to the brim of clothes, home goods, and nick nacks and aren't aimed towards getting out of towners to drop serious doe, but more to cater to families that are just looking for cheap necessities.
Shopping is a sport for me and I am definitely on the A team ;) I find the best stuff at thrift stores that were around long before thrifting was "cool." There is a ton of crap, yes, but within all the junk you can find some treasures and not break the bank.
As stated before, I have a serious shopping addiction that I have managed to get control of, but when I need a good fix, I hit the Family Thrift Store in my neighborhood. I got all this kid stuff for under 10 dollars, which left some extra money for me to spend on ME! The denim dress on the left is from A Children's Place, the leotard is Danskin, the black and white dress is from H&M kids. The overalls for Ezra are Levis, and the little matching set is no brand but its RAD and well worth the 2 dollars spent.
Oh yeah and did I mention I got some stuff for me too!? DUH. Three outfits for under 20 bucks. Yes please. I cut the sleeves off the denim shirt and am rocking it today with different shorts. The denim shorts are Paige and nothing else was brand name but all of it looks super cute and well worth the money.
Ivy has gotten quite good at thrifting too, a little too good if you ask me. She always finds the coolest kid toys and I usually let her get them because the price is right.
So next time you get the itch, avoid target, avoid Armitage, AVOID MICHIGAN AVE. and go shop at your local thrift store. Just make sure you are prepared to dig and spend some time. I also never really go in with a mission in mind, just go with an open mind and patience and you'll come out with some great stuff.... at least I hope so :)