What neighborhood do you live in and how long have you lived there? I moved to Chicago about four years ago—I originally lived in Logan Square and then I moved out to Lake Forest, a suburb north of Chicago.
Where do you put up friends visiting town? Virgin Hotel Chicago. They've always got the best visiting musical acts, great coffee, and wine in their Two Zero Three wine bar, comfort food at Miss Ricky’s restaurant, and unbelievable views from the Cerise rooftop (203 N. Wabash; 312-940-4400; virginhotels.com).
Where is the best place to find your hometown’s signature dish? It’s Chicago, so the signature dish would have to be deep dish pizza. There is no better place than Pequod’s in Lincoln Park. I always get the deep dish pepperoni—it has a perfectly caramelized crust (2207 N. Clybourn Ave.; 773-327-1512; pequodspizza.com).
What is your favorite restaurant to take visitors? One of my favorite restaurants to take people is a place called Avec, right on the edge of the West Loop. It’s Mediterranean-style shared plates with a killer wine list. They have these bacon-wrapped dates that are unbelievable (615 W. Randolph St.; 312-377-2002; avecrestaurant.com).
Where would you go for cocktails? I recommend Sable for cocktails. They love to ask for your input—what you like and don’t like, and they try to offer you something new. I love it (505 N. State St.; 312-755-9704; sablechicago.com).
Where would you choose to splurge on a night out? Definitely on food. Le Colonial (937 N. Rush St.; 312-255-0088; lecolonialchicago.com) and Alinea (723 N. Halsted St.; 312-867-0110; alinearestaurant.com) are both great excuses to celebrate.
What is your go-to after-hours bar? Violet Hour in Bucktown is an incredible speakeasy—one of those places you wouldn’t even see if you weren’t looking for it (1520 N. Damen Ave.; 773-252-1500; theviolethour.com).
What’s the best way to spend a Saturday afternoon in town? There’s a concert venue called Ravinia that’s like an amphitheater. You can sit in the theatre or outside on the grass and have a picnic. It’s just great being out on the lawn having a cocktail. Outdoor music series are my favorite way to spend a Saturday (200 Ravinia Park Rd.; 847-266-5000; ravinia.org).
What is your Sunday morning routine? Our Sunday morning routine is very much breakfast-oriented. I have one-year-old so our Sundays start very early, as most days do. We normally go and have a breakfast at Lula Café in Logan Square where I enjoy their Royale [a breakfast sandwich with beef short rib, cumin aioli, orange jam, aged cheddar, watercress, and egg on ciabatta] and the Chicago Tribune. Everything is so good. The Bloody Mary has clam juice in it, which won't please some people to hear—but when you taste it, it’s amazing (2537 N. Kedzie Ave.; 773-489-9554; lulacafe.com).
Where do you go for the perfect cup of coffee? La Colombe. They have amazing lattes and delicious drip coffee in the West Loop (955 W. Randolph St.; 312-733-0707; lacolombe.com).
What’s your favorite view in town? Chicago’s Shedd Aquarium juts out into Lake Michigan and offers an insane view of the city. I love to walk out along the water there. If you walk way out to the point behind the Planetarium, it’s the best view of the skyline of Chicago (1200 S. Lake Shore Dr.; 312-939-2438; sheddaquarium.org).
What’s your favorite path or trail to follow on a walk? Everybody says it—but I love to walk along Chicago’s lakefront. In the summertime it feel like everyone in the city is out and active. The bike path goes all the way from north Chicago to south. If you were a lot more in shape than I am, you could ride to Indiana.
What are your favorite offbeat cultural attractions? There’s a couple of well known museums that everyone goes to but no one ever actually goes to the Chicago History Museum (all my wife’s family who have lived here for all their lives, had never even been to it). I only know about it because I did a shoot there. And it’s really great. It’s more of a cultural center but they’ve done some showcases of fashion designers, and they’ll have special art installations. The Chicago Museum scene in general has so much to offer, from the Art Institute to the Museum of Science and Industry. I love taking my daughter there and watching her take it all in (5700 S. Lake Shore Dr.; 773-684-1414; msichicago.org).
What’s your favorite shop or boutique? I like shopping for my wife; and there’s a store called Ikram that has everything. The best thing there is the jewelry—it’s very weird and eclectic. Some of it’s vintage and some newer collections. She also does home goods—I got a glass olive oil and vinegar mixer, which, is just the most bizarre looking thing but it's amazing (15 E. Huron St.; 312-587-1000; ikram.com).
What’s the ultimate souvenir from your town—something you can only get there? One gift I always like to give to visitors is a copy of The Devil in the White City by Erik Larson. It’s packed with history about Chicago and the World’s Fair, but with a murderous twist.
What’s the best-kept local secret? Chicago has a trove of free museum deals. With museums like the Art Institute of Chicago being rated No. 1 in the world, that’s a pretty unbelievable deal (111 S. Michigan Ave.; 312-443-3600; artic.edu).
In our Hometown Guides series, we're seeking the best restaurants, bars, vistas, and things to do in a given place from the people who know best—the artists, designers, chefs, and store-owners who live there. See more Hometown Guides »
Image Credits: © Derek Richmond; © Shedd Aquarium/Brenna Hernandez