Don't forget to visit the landmark of nepali neighborhood. Singh Durbaar. :D JK. You can use zip car; its cheap and there are enough zip car location within chicago to get a car. if not try CTA Passes. Weekly passes for $23. But why would you like to visit chi-town in winter??? just askin. Transportation solved. need a place to stay? you mean where? as a guest with other nepalese living in Chicago? if yes than it would be a tough time finding someone. If no; you can always find plenty of motels and hotels, inn within chicago. BTW where you coming from?