You will Love Michigan Avenue....also known as the Magnificent Mile.
I lived two years in Chicago, and I miss it dearly.
But to answer the original question, my choice would be a lifetime money's worth of permanent hair removal, a 40 foot sailboat docked in a coastal town where I can go anywhere, and a couple of cool expensive guitars, and send kids to college. That's about it....don't need anymore. I'm fully happy. The rest requires human company.