Look NORTH on the Tri-state. You'll be commuting opposite general population. In the morning, NB will be a parking lot while you'll be barrelling along at 70mph. Same in reverse, except for Friday afternoons in Summer, when everyone is heading to Wisconsin for weekend. There's some decent short-term apartment rentals in Northbrook, near Palwaukee airport.

Actually, working in Rosemont gives you many options. N/NW suburbs are accessible. City is accessible. Near west suburbs are accessible. S 'burbs are accessible. Don't now about S/W, might be a commuting stretch.

Housing will greatly be dependent on budget. Will your office be near an "L" or Metra stop?