1. Take the green-line to Oak Park, not only for the Frank Lloyd Wrights, but to have a glimpse of the urban blight and brownfields that form a ring around the city proper. Chicago is a city of skyscrapers, but everything drops off dramatically past the city core, which makes for both a visible inequity of wealth and a densely festooned downtown. Some much needed perspective.
2. You CANNOT see the Art Institute in less than a whole day. You just cant, unless 4.55pm appeals to you. You come for the Seurat (huge! unexpected border!) and the Toulouse-Lautrec (creamy-bright!) and that's all fine and well, but they have a section on midcentury black American photographers and a room devoted to miniature rooms. MINIATURE ROOMS. Those two alone will set you back like three hours...
3. North Dearborn is the swishy Italian resturant mecca. Be prepared to drop your rent money and grin like an idiot the whole time. I have never tasted such food. (or unoaked riesling)
4. Take the architecture boat tour. Take the architecture boat tour.
Take the architecture boat tour. I would LIVE on that boat if they let me.
5. You can walk three abreast on the street without bothering anyone. It's okay. After the fire they made the side-walk extra wide, presumably for people like you.
6. Try to sneak into as many building lobbies as you can. They're usually totally beautiful inner sanctums of Chicago School-era peace and tranquility. Gold art deco elevators abound.
7. What the hell is it with these people and oatmeal? It's on practically every menu.
I bet the italian restaurant would carry it if it could. Oatmeal is disgusting.
8. Sit in Frank Lloyd Wright's studio. Eat sun chips.
all photos sourced from the Chicago Postcard Museum