Got a day off with the family and a burning desire for a good time—and let’s be honest, good eats—around the Windy City? Follow in the footsteps of Joe Flamm, winner of Top Chef season 15 and chef-owner of one of our favorite Chicago restaurants, Rose Mary. He offers up his perfect “Sunday Funday” itinerary, a road map for how to spend a day in the city when responsibilities have been tucked away and there’s nothing but good times to be had.
Start in: Beverly, South Side
End in: Pilsen, Lower West Side
When I’ve got a day off to play with my family—my wife Hillary and our kids, Luka, age three, and Sydney, just four months—we go for casual, easy, and fun. We live in Beverly down on Chicago’s South Side and our biggest thing is to stay around the neighborhood.
Starting the day with coffee and pancakes
If you’re like me, coffee is before anything—and so should be my favorite nearby coffee shop, Two Mile Coffee Bar. I live in a very old neighborhood in a very old house, but there’s a younger generation of people in Beverly who’ve come to create here. Family-owned Two Mile is a great example because it’s newer but has an old feel to it. Plus, no one minds if you’re walking in with screaming kids and they make a really nice “red eye” [coffee with a shot of espresso—the morning version of a beer in a shot]. My three-year-old son loves making pancakes with me, so we’ll come back home to make sausage and blueberry or chocolate-chip pancakes, depending on how chef Luka is feeling that day.
Getting outside in Chicago’s South Side
We’re Southsiders through and through, so when we want to get the kids outside, the nearby Dan Ryan Woods is a really amazing park. It’s the highest point in Illinois at 66 feet, which isn’t saying much. But it’s surrounded by trees with views of the Chicago skyline and there’s lots of places for kids to run around. It’s also super pretty at any time of year to walk along the shore on Promontory Point, a picturesque peninsula on Lake Michigan that’s an extension of Burnham Park.
Every grown-up should have a really great [go-to] flower shop, otherwise you’ve lived a mistake-free life. So when the kids are napping, I might run out to Oak & Bloom for a knockout custom bouquet. If we’re making lunch or dinner at home, I’ll also stop by a great Italian store in my neighborhood called Calabria Imports. They sell Italian cheese, prosciutto, and giardiniera, but their Italian sausage is my favorite. If the kids are up and we want to eat lunch out, Fontano’s Subs is the place for great Italian sandwiches. I’m a “Bada Bing” guy and you’ll love that sandwich, too, if you’re a fan of capicola, pepperoni, salami, mortadella, provolone, and swiss.
Finding outdoor art (and tiring out the kids)
If you want to get to the heart of the city, it’s fun to take the kids to the Loop. My son would be happy just watching the “L” trains go by, but we zero in on Chicago’s big outdoor art installations. There’s the Picasso in Daley Plaza and great statues further south in Grant Park, where you’ve also got the Museum Campus with its “Agora” sculptures—all really great places to walk around with young kids. Right off the Museum Campus, my kids love the Shedd Aquarium. I think it’s the best kids’ museum in Chicago because they seem to have the most kid-friendly exhibits and there’s enough room for kids to run around being maniacs. And you know what’s nearby for an awesome dinner? Eleven City Diner. It’s super kid-friendly, approachable, and fast with great sandwiches and awesome quality food.
Finishing up with dinner and drinks
For dinner back on the South Side, Horse Thief Hollow brews great beer and supports local suppliers and artists. It’s easy to pop in with kids and they serve fantastic buffalo shrimp and burgers. If we’re leaning toward cocktails and mezcal margaritas for the parents, we head to Unidad in Evergreen Park. They serve the best cocktails on the whole South Side. We also live by one of the greatest ice cream places in Chicago, called the Original Rainbow Cone. It’s got a five-flavor “Rainbow Cone” and is three blocks from my house, so that’s the spot if the family has stamina for dessert.
If me and my wife can get out for a late cocktail and dessert without the kids, we like to go to S.K.Y. in Pilsen for a spot at the bar and out-of-this-world desserts by Tatum Sinclair, one of the top pastry chefs in the city.
There are also two places next door to each other in Bridgeport that are quintessential South Side joints. Maria’s Packaged Goods is a cool old school slashie that’s a liquor store in front and a bar in the back—just like out of a movie. Go through a side door and you’ll be in Kimski, a Polish Korean joint that’s super good. I haven’t been yet, but Osito’s Tap in nearby Little Village is number one on my list to check out. We’re always dying to get back to Virtue in Hyde Park, too, because if it’s not the best restaurant on the South Side, I don’t know what is.
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