Just looking through http://chicago.craigslist.org/search...sk=&maxAsk=100, I see plenty of interesting options:

http://chicago.craigslist.org/chc/bik/3380196073.html Fenders!

http://chicago.craigslist.org/chc/bik/3364177734.html Italian Mixte SS with a rack (but a woman's frame)

http://chicago.craigslist.org/chc/bik/3379972251.html does chicago only have woman's frames? Two for $70, try 'em both, keep the good one, sell the other

http://chicago.craigslist.org/chc/bik/3379557677.html this looks like it would make a great commuter (unless you're set on a road bike)

http://chicago.craigslist.org/chc/bik/3372349300.html some pretty-good looking vintage here (but only 10-spd)

http://chicago.craigslist.org/chc/bik/3343561141.html two sub-$100 Trek's here, one with a rack, one with fenders

Personally, I think most of those options are better than the Le Tour you originally posted. I'm thinking Chicago is pretty flat, right? I'd go for the Chiorda, it would be a sweet ride even though it's a woman's frame, and you could probably sell it for a profit once you save up for bike N+1