Long linked with architecture, including the Wrigley buildings, Frank Lloyd Wright, and even Anish Kapoor’s bean-shaped Cloud Gate, Chicago has gained tremendous ground as a fashion and style capital too (with some thanks to the First Lady). Here, legendary Chicago retailer Ikram Goldman (whose 16,500-square-foot eponymous store, complete with café and gallery, is a destination itself) opens her address book.
Soldier Field I don’t think anyone would really recommend a stadium, but you get some of the best views of the city from the mezzanine skyboxes here. Plus, you get to watch the Bears. 1410 S. Museum Campus Drive, (312) 235-7000; soldierfield.net
George Greene This men’s store in the Gold Coast feels like a whiskey-cigar smoking kind of place, very old school. My husband shops here. The three owners — John, John, and Edmund — had all been working at Ultimo, a Chicago fashion icon, but when it closed they decided to open this place. Their tailor, Oscar, knows a man’s body better than anyone else. Great collection with Zegna, Yohji Yamamoto, and of course made-to-measure suiting. 49 E. Oak St., (312) 654-2490; george-greene.com
Alinea If you have all the time in the world and you can sit for four to six hours, this is the place. I have never been anywhere where the food presentation is as fabulous and delicious as the food itself. The dessert alone is worth the trip, like performance art. 1723 N. Halsted, (312) 867-0110; alinearestaurant.com
The Aviary There is such artistry to the cocktails here; you don’t just have a whiskey with ice and a cherry. Each drink is a delicious concoction. Even the glasses are custom-made, and it has the sexiest couches. 955 W. Fulton Market, (312) 226-0868; theaviary.com
Mies Van Der Rohe buildings The Europeans always come here in search of his buildings — the Federal building, office towers, the Farnsworth House. He was such a visionary and introduced us to modern architecture and this modern way of building. He and his peers led the way for young architects at that time.