So, I don’t know if this will help you, but I’ve come to some fun free stuff I like to do. Now, since you live in Chicago, most of this should be fairly easy.
1) Walking and looking. Really, I just love to walk. I usually get off the el at the downtown loop, head to the lake, and then turn in one direction and start exploring the city. I have a tendency to venture into public buildings, walk all the way to the roof, and then work my way back down, exploring every level. I swear, it’s fun!
2) Take pictures while walking. I have a digital camera, so this is no longer an expense for me. I can go buck wild and come home and play around with them on my computer. It’s free and fun for me. Also, sketching might be another option, a little more cost, but still hours of fun for very little.
3) Museums. Can’t really beat the free ones.
4) Book stores. So, you just get all the really huge, really expensive, art books, sit down, and indulge. Or maybe grab all the magazines you want to buy and read them there.
5) Library. Again, with the free books.
6) The Lake. All that land, what I like to call, Chicago’s Front Yard. I know it’s cold now, but just bundle up!
7) Volunteer. You might be able to find something really cool to do. Not only is it free, but you can feel good about giving of yourself to others!
I work hard on finding free or free-er things to do that will take up a lot of time and are fun for me. These have really worked out for me, so I hope maybe I’ve provided some good suggestions for you. And don’t forget that a country drive, or a drive on the Sheridan Road can cost just a tank of gas and be a whole day’s worth of fun and exploring!