gorocks99
PM me with stuff you like to do/eat/see and when you're thinking of coming - there are a ton of festivals in Chicago during the summer, I can point you to the best ones from my experience and maybe find you some discounts too (free museum days, etc.).
My generic advice for saving money and having a good time is -
Avoid eating/drinking on Michigan Ave or in the Loop for the most part. Things will be overpriced the closer you get to downtown. Instead, get out into the neighborhoods and explore. CTA makes it pretty easy to do so, and there are really awesome places to eat everywhere in the city so don't be afraid to branch away from the tall buildings.
On those same lines, find out where you want to go and don't just wing it. It will save you time, and save you from ending up in the wrong area. There are neighborhoods - even on the north side - where it switches from safe to not-so-safe pretty fast.
Don't drive. Parking will cost you a lot almost anywhere you go.
Most summer festivals are free to enter and offer good people watching. The food and beer prices will be inflated at most of them, however, so be prepared for that.