Just wanted to thank you all for this list. I was able to get donations from Outerwall (Redbox tickets), Green Mountain Coffee (6 bags of Coffee). I wasn't able to do many of them because our event is in December and most of them asked for a minimum of six weeks notice but I bookmarked the list for an early start on our next event!

Brittany,
Try you local museums, attractions, etc. Go online to the Chicago area tourism council and find some ideas through that of who to contact. Do a search here on the site for "Chicago" and see what comes up.

Does anyone who has done a raffle for Chicago know of any good places that will willing donate?

I found that the best way to find donation requests in my area is to do an internet search with the text: donation requests <insert state>
For example:
donation requests texas

This will give you organizations that are in your state and have someplace on their website with the text donation requests.

You will get a few non profit orgs that are soliciting request; but, most often, you will be navigated to the web page that has the instructions for how to request a donation.

For anyone who has used donationmatch.com, how far in advance did you post your event on it? Our raffle is the first week of May for a Catholic elementary school.

Thank You

Red box: coinstar.geocko.com/inkind/request