Chicago is the third largest city in the US. Its also pretty inevitable you'll end up here if you're hopping freight around the US. Train hub of the Midwest right here. Easy hop outs and tons of yard to scope.
Chicago is segregated by class and by race. Every neighborhood is a different slice of life and culture. Spend time in a bunch of them, they've all got something to offer. The north side is where white yuppies thrive. The west side is working class central and south american. The south side is working class black. Near south is working class white and asian, largely chinese. Northwest is quickly gentrifying, as is near west. Spots like Wicker Park and Pilsen, where travel punks would normally find each other, are starting to fade out.
Winters here get cold and the snow gets heavy. If you aren't prepared for negative 20 degree weather, don't come through between december and february. we get shit called polar vortex here, which can send temperatures down to negative 50 with wind chill. Not even safe to ride through during that. dont try it.
Food & Shelter
Vegans can spange up around boystown or wicker park and get Chicago Diner pretty quick. Great food, easy kickdowns. There's a bum feed every day that bounces from neighborhood to neighborhood, and Grace Place downtown will house you for a night and feed you in the morning but you cant count on it long term. Chicago has hella alleys, so dumpsters are easy to come by if that's your thing. Grocery stores are generally harder to dumpster in chicago than in other places, but you can still score. Catholic Charities has open pantries on the south side about 4 days a week, and they hook it up fat.
Downtown parks are a no-go most of the time. Park security will bother you, but usually no risk of arrest unless you're acting up. Tent cities exist around most of the interstate ramps and highway exits, especially on the near west and near south. Grace Place downtown is good for a night or two, but dont count on it. You can find squats and punk houses on the west side if you're a social butterfly and talk to people who look like they might know, but you cant just wander into them around these parts.
Things to see and do
The Loop spange is crowded and varies. If you can busk, you'll have a lot of competition. Avoid Wrigleyville on game days, thats how you get jumped. If you're queer, you can pull kickdowns in Boystown pretty easy. If you aren't, you won't have a ton of luck there. During spring and summer there's always shows to play, so if you are a musician get to talkin to punks and you can land a back yard stage pretty easy.
Hitching in is simple from any area, most roads lead to here eventually. 290 will take you right to the loop, 90/94 will take you northwest/southeast through the city. 55 will get you around the south side and out to St Louis in a straight shot.
UP, BNSF, Norfolk, and Southern all run mains through here. If you're chasin freight, you might have to hop out on the move cause you dont wanna end up too deep in the yards here. make sure you know your line getting out and you wont have any real issue, yards here are very active and youll be able to catch something pretty quick most of the time.