Can i work for a room? Idk if that is still a thing but if i may i would like to work for a room is possible.

Great question! Sorry i have no answer to that one though.

Not sure, but since it's not a usual youth hostel, my inclination is to say no. You might want to touch base with HI-Chicago. Hostelling International does offer such opportunities, but I'm unsure of the guidelines. HI-Chicago is a gorgeous hostel. Check the website. It's much more socially organized than other hostels in Chicago and still convenient to everything. It's a show walk to Millennium Park and right on the Blue Line. Good luck!