Chicago:Shop: Uprise: 1820 N. Milwaukee ave.
http://www.upriseskateshop.com/ the hub of skateboarding in chicago (the suburbs don't count, ha!)
Spots: just go downtown, sundays are best, but generally after 7 is good and if you skate in the loop wait until the bike cops are off work at 11:00. Unlike say, LA (BOOOOOOOOO) you can actually skate spot to spot ( at least downtown) and or just take a train to some other neighborhood and explore.
wicker park has some spots ( the neighborhood uprise is in), Clemente high school is skater central
Transport: the public transport, though getting more and more expensive the CTA is where it's at, and if you get a day pass, a week pass, or a month pass, avaiable at any check cashing or whatever place, it's a bargain if you take the train/bus more than twice a day.
Food: i miss chicago food so bad
Pequad's pizza is a must, at Webster & Clybourn, the best Chicago Pizza, $5 lunch special is the best, a small ( not that small) pizza and a beer, so gooood.
Billygoats, it's downtown, it's cheap, it's on lower wacker drive (another good skate spot for the colder wetter days)
Pizza Metro, again, wicker park, another skater hub
Potbelly's, a chicago chain that makes good subs
... there is so much good food in this city
Skateparks:Wilson: on the northside, fairly easy to get to on the train, good bowls, some street stuff, is lit up at night
31st: a great idea poorly executed but still very fun, this is on the southside, it is tough to get to by bus, it can be done, but driving recomended, not lit up at night
the new ledge park: it's in the south loop... i forget the address, but it's dope, lots of recycled plastic benches by this cool dude Dan Peterman.. it's a little south of the art institute (which used to be a great spot), the park is lit up at night.
so that's that, go to Uprise, go to Pequads, skate the ledge park until 11:00, then go skate the loop and that's a good day
CHI OR DIE!