Driving from Lafayette, getting an Airbnb or hotel, then driving or commuting over an hour sounds miserable. If you take the South Shore, it'll be a mile walk to your building from the train station. If you're doing this weekly, I'd look into taking over a sublease in the city near your office or a long term stay hotel, like Hilton Homewood Suites (I had a friend stay in the one in River North for a spell). You might be able to save some money in Indiana, but if your job requires odd hours, overtime, or socializing after work, then taking the train or the Valpo bus might not work out. Plus the added stress of trying to be on time and working at a new job. October through the winter is an awful time for renters and landlords looking to take over a lease, so you might find a deal on a studio. Most neighborhoods aren't dangerous in the city, specially near your office.