This would take some work, but would be well worth it.
Host a fundraising dinner. Have people sign up in advance for $x/plate. Cater the event and have the jazz band play music during the dinner. Get a quote from the caterer, and base the per plate price on that (plus extra to go to the PA) so that the band comes out ahead. Around here, you can get a caterer for a served sit-down dinner (salad/dinner) for about $15/plate, but for a fundraiser, you could charge something like $25/plate.
It's all about the atmosphere/experience, something like "A night of dinner and Jazz." You know, dim the lights, candles on the tables, live jazz band performing. I would forgo the tip jar in such a setting (you're making money per-plate) but announce that if anyone wants to make a special contribution they can do so and tell them how.
I like this idea, but here is how I'd improve it:
1. Don't cater it: too costly. Instead make it a spagetti dinner or better yet: Lasagna dinner night: Get a few parents to volunteer to make a Lasagna. Get some already bagged letuce and grape tomatoes with a vat of two or three dressings.
Lasagna recipe that worked for our HS Band Boosters (this is strictly from memory, so it's not perfect):
*Lasagna pan: (12" X 24") give these out at a meeting with the written recipe
*Ronzoni Lasagna Noodles (the ones that don't need to be boiled) (I think 2 boxes)
*Classico Tomatoe and Basil Sause (3 jars)
*already shreaded mozzarella cheese (2 lbs)
*Poly-O ricotta cheese (2 lbs)
* Kraft parmisian cheese (half a can)
*1.5- 2lbs chopped meat
*basil (1 TBS)
*oregano (1/2TBS)
* parslie (1 TBS)
1. cook the meat in a large sause pan, drain and add the sauce. Cook for a little while longer
2. In a separate bowl: mix the parmisian, ricotta, basil, oregano, parslie, mozarella all together. If it's dry and unmanageable, add some sauce to loosen it up.
3. In a lasagna pan, layer this way: a. sauce with meat, b. noodles, c. cheese mixture, d. repeat a-c three more times, then top it off with a layer of sauce and shreaded mozzarella
4. bake (I don't remember the temp or time) ask some moms or look it up on the internet at a cooking website.
5. If I remember, each pan gave us 15 or 18 large portions (3 X 5 or 6)
Have the few parents cook these and deliver them 30 minutes prior to the event. Have the salad ready and some dinner rolls you can get at BJs or Sams Club.
2. Charge only $10. You will get more people and you will make more money since the parents are making the lasagna.
3. Advertise the event and include a picture of a PA system and the band.
4. Another idea is to include the concert band in on the event. Make up some story of how the PA can be used for all school concerts. I'm sure the concert band has way more members (hense more families/parents) and therefore a much greater pool of ticket sales. It worked for our high school bands for other financial reasons.
Good Luck!!!