Hotel Hunting Tips -- for Chicago but for anywhere really

Gonna be spending a few days in Chicago at the end of September and trying to scheme a way to get a good deal on a hotel.. SO... first off, any good suggestions? just really want a decent place to put my head and sleep, gonna be exploring the city and flashmob robbing walgreens with some under privelaged youth maybe once or twice a day... and ideally finding some good hole in the wall food places, so preferably somewhere that has decently good food places as well..

Has anyone ever used priceline, hotwire or any other 'make your own price' site to great effect? is it better to book hotels farther out or closer to the scheduled time both normally and through these sites?

Any general suggestions on hotels? Since im a poor trader im trying to spend under 150 a night, cheaper the better ;D preferably 120 130 but if can be done cheaperi ll take it lol

 

I lived in Chicago for a week for around $30 a night. Of course, I was a poor student so $150 a night was kinda out of range for me. Look up Hostel International or Chicago Gateway Hostel (gateway is pretty close to downtown Chicago). By the way, these were dorm style rooms with bunked beds and a locker. If you're looking something a little better, I think they have double rooms for $100 a night (not sure on this one though).

 

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