I did my first trip in 08 after thinking about it for many years. don't think just go!
Join the EAA if you haven't already member discounts ect.
Hired a car at o'hare and camped to be close to the action.
Travelled light and bought cheap camping gear at walmart everything i needed including camp chair and esky for under a hundred bucks. empty tent and put it in the car as the area will puddle up in rain. donated it all to the south african guys as they return each year and leave their stuff stored.
on site food requires a detox. camp ground security is very good but take usual precautions. amenities are pretty good and more added each year. school buses will take you to various locations around the field including the museum (a day in itself) and seaplane base, (great in the heat of the day)plus into various shops and discount outlets in town. On field there are 'trams' to hop on and off at various points of interest. i gave away many little badges and like others have said it pays but just the warm smile and response is worth it. Banks and post office shipping agents all on site. you can buy a little radio and listen to either the EAA radio or the tower. Airshow every arvo. enjoy the lack of barricades and friendly flight line marshalls. try and get there a day or two early you can wander every where and watch a lot of aircraft arrive.
spend a little extra and fly in something we don't have back home. i did the B17g
. when you walk out at the end of your first day try not to feel like you were born in the wrong country.
On the way back to o'hare i stopped off to visit the harley davidson museum at milwalkie. not a big fan of them but but my two brothers in law wanted a t shirt each. pretty impressive and ended up taking almost 3 hundred photos. keep a weather eye out as it is tornado season.
enjoy