Lots of places within a couple hours driving distance to play... Apoc, Siege, Edge towards Madison, Boneyard and Commando to the north, Brew City around Milwaukee, and PBX in the north Chicago burbs. Badlandz, CPX, and Blast Camp are also in the area.
Team practice is pretty heavy on Sundays though. You might be hard pressed to find a spot to jump in if you don't have 5 guys.
Brew City (Milwaukee), Alienman (Madison), and Paintball Sallys (Kenosha) are the best proshops around.
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