When we did our chili night we combined it with a bingo night. We asked retailers throughout the city to donate gift certificates or items to be used as prizes. It was a huge sucess.

Use your fundraising event to raise more money than you would with just Chili. Like a spagetti dinner, pancake supper, and so on, your chili event could employ some of the same ideas. (Have you considered having a chili cookoff? Sort of a recipe competition idea.)
Don't forget to use what I like to call an overlay. That is, use this gathering of supporters to raise more money by selling other things as well. Instead of just selling chili, sell baked goods too; have a cake walk to make more money from those baked goods than you would by just selling them outright. Sell pizza discount cards which are always a big money maker.
Boost your event by getting as much publicity as possible. Many radio stations, tv stations and newspapers will announce your message free if you are raising money for a school or nonprofit.
Here's where you can find more ideas for school fundraisers . Check this website to get ideas for overlays and look at the articles on spagetti dinners and pancake suppers too. They may offer additional tips.

Do a rock, paper, siccors tournament, have games spread about like cards etc, have a parent/son paper plane making contest (with rules and the one that flies the furthest wins), or a bingo game. You can keep it low key and low effort but still fun.
d

We bought an inflatable bouncer from BouncerLand - US Manufacturer of Inflatable Bouncers, Slides, Combos, Jumpers and are going to use it for a long time fun because that's one of those commercial things the rental services use, and i know that they use it for years of rental and renting every other day .. and with our not-heavy use we gonna keep it for many years

The kids love it, and we are saved from hassle of repairing it every time or buying a new one like it happened with our previews one (a china-made)

We always have hot dogs with our chili for kids (and adults) who don't like chili, but still want to come. We also ask our parents for single-serving sized donations of cookies, brownies or any other dessert that can be put in baggies. Any homebaked goods must have the donator's name on it, and each bag has to be labeled with what type of dessert is in it. This helps those people with food allergies.

Last year, one of our parents made a bunch of games from old scraps that she had at home. We had a duck pond (Ok...so we bought that one), ring toss (she painted old bottles different colors), bean bag toss (she took an old picket fence and placed baskets on it), hat toss (she took an old folding closet door and screwed in different types of hooks and knobs). We also had a putt putt game and a cake walk. For our cake walk, any homemade cake had to have the donator's name along with either the recipe or a list of ingredients.

One other year, we had an inflatable bouncer.

HTH!
Melissa

corn bread, salad, dessert bar(myo sundaes or desserts w/a western theme- cowpoke something-or-other. I've learned from my own kids that if you give something a fun name, they will eat & like just about anything).