You would need many upsets from a 4-4 team to reach 256 and you have 8 4-4 teams that are playing each other
Naz vs Benet
Morrison vs Erie
Richards vs Ag Science
Maine West vs Highland
St Pats vs Viator
Noble vs Clark
Toulon vs Princeville
Nokomis vs Dupo
I will give a few upsets that need to happen
Rock Island over Quincy
Hinsdale over Glenbard west
Orion over Rockridge
Rolling Meadows over Mt.Prospect
Buffalo Grove over Hersey
Oak Forest over York
Bartlett over Glenbard East
Joliet West over Plainfield South
New Trier over Maine South
Lincoln over Troy Triad
Flora over Carmi
Morton over Washington
Marian Catholic over Carmel
Mt.Vernon over Mt.Carmel
Lisle over Peotone
Deer Creek over Eureka
Hillcrest over Oak Forest
Illini west over Macomb
Casey Westfield over Olney
My projection is that 4-5 4-5 teams make the field and you have a few games in 1A -3A that can go either way with a 4-4 team so it could go up
1-Buffalo Grove
2-Oak Park River
3-Barrington if the beat Fremd
4-Benet
5-Rolling Meadows
6-Hinsdale Central
(Wheaton Warrenville wins they are in ) up to 2nd team in
7-Glenbard North