Moving in Chicago is its own thing. Between high-rise loading docks, residential parking permits, and tight side streets, the prep work matters as much as the muscle on move day.
Two to four weeks before your move, confirm your move-out and move-in dates with both buildings. Most downtown buildings require a certificate of insurance from your mover and a reserved freight-elevator window — these book up fast on weekends and at month-end.
If you're moving from a street-parked address in Chicago, look up your ward and request a temporary no-parking permit through the Department of Finance. Without it, you may end up carrying your boxes a block.
One week before, finish a first pass of packing: closets, books, decor, anything you won't use this week. Label every box with the room and a one-line summary of what's inside. Future you will thank present you.
Move day, keep essentials with you: keys, IDs, chargers, medications, and a small toolkit. Your crew will handle the rest.