It's driveable for me so i'm semi in.
Chicago has lots of $200 hotel rooms and fewer $70 hotel rooms, so somebody good at planning or who knows the area should check around. The further out from the city, like hammond, the more there are $35/night hotels.
I'd suggest a designated "hospitality suite" type room that we all split,and the broke folks can sleep on the floor while the funded folks can get their own room. It's a step up from us all staying at crabby's.
Maybe there's a nice or gullible person in chicagoland who would like weekend guests, from which we could stage predawn raids excursions into the city. We could put a listing in craigslist chicago.
There's a youth hostel on the north side. I usually just walk around boystown all night or drive home. I know just enough about chicago to be able to point people towards the loop, art museum, boystown, chinatown, but it's important to have a local guide.
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woof