When we wanted dining recommendations, we went straight to a local maven: Catherine De Orio, the culinary consultant, chef, and food and travel writer who edged out more than 900 candidates to be the next host of TV restaurant review show “Check, Please!” The rub: “I can’t play favorites,” says the former attorney-turned-brand ambassador who would only disclose that the minute she got the news, she went straight to Johnnie’s Beef (7500 W. North Ave., Elmwood Park, 708.452.6000) for Italian beef sandwiches to share with her parents. Luckily for us, the stylish Elmwood Park native piled on the suggestions for a whole trip’s worth of things to do in Chicago. Considering she’s been known to throw elaborate tiki parties complete with fish swimming in the bathtub, this is a gal who knows how to entertain—and be entertained.
I tend to gravitate toward simple silhouettes as I love statement accessories and find they are a better backdrop for letting my shoes, bags and jewelry shine. My go-to brands are Kelsey-Tanner O'Connor (an amazing local designer—her boutique Decollage is in my neighborhood—very dangerous!), Helmut Lang and A.L.C. Kelsey designed a dress and named it after me: The Cat dress (Cat is what my close friends call me)—it's amazing; I have it in multiple colors! 1219 W. Madison St., 312.226.8087
Material Possessions and P.O.S.H. Chicago
I love to entertain and I am somewhat of a housewares hoarder—two of my favorite places are Material Possessions (704 N. Wabash Ave., 312.280.4885, www.materialpossessions.com), which has fabulous tabletop items in addition to cool home decor and jewelry; and P.O.S.H., which has unique accessories for the home and table with a great selection of flea market and estate finds (613 N. State St., 312.280.1602, www.poshchicago.com).
ART (AND ARCHITECTURE) FOR ALL
Modern Wing at the Art Institute
My career started in museum work at the National Gallery of Art and Guggenheim, so I am a sucker for amazing art collections—Art Institute is a must see and the Modern Wing built by Renzo Piano is incredible. 111 S. Michigan Ave., 312.443-3600, www.artic.edu
The Architectural Boat Tour is kind of a home run every time. Even if someone isn't particularly interested in architecture, it is a spectacular way to see the city. Chicago’s First Lady, Southeast corner of the Michigan Avenue Bridge, www.architecture.org/tours/boat-tours
Drumbar not only has one of the prettiest rooftops in town, its drink selection is stellar—and you can't beat a place that offers more than a dozen rosés by the glass. 201 E. Delaware Pl., 312.924.2531, www.drumbar.com
The Green Mill
The Green Mill is hands down one of the best places in the city. Live music, old-school drinks and an awesome lounge-y vibe—love it. 4802 N. Broadway St., 773.878.5552, www.greenmilljazz.com