If you want to know what you can do in 36 hours in Chicago, just ask R’el Dade and Marcus Lloyd. Lifestyle bloggers and creators of The Place I Was Telling You About, this duo travels the world to uncover the simple pleasures, such as finding the best cup of coffee in town to the perfect spot to shop for something original. For a visit filled with adventures and munchies, just follow their tips for a long weekend in the Windy City.
Head to Homestead on the Roof (1924 W Chicago Ave.) for literal farm-to-table dining. All 85 outdoor seats in this cozy, tucked-away spot have a view of the 3,000-square-foot rooftop garden, which influences the direction of the seasonal menu.
Keep the party going outside at Cerise (203 N Wabash Ave.), located 26 floors above the Chicago cityscape. Enjoy cocktails, culinary creations, and cozy panoramas late into the night.
World-renowned latte artist Hirosho Sawada’s Sawada Coffee (112 N Green St.) is one of the best places to order an espresso or matcha tea. At his first U.S. location, kickstart your day with a game of ping-pong and artisanal handcrafted donuts from Doughnut Vault. Or, if you’re up for a journey, the Heritage General Store (2959 N Lincoln Ave.) offers award-winning coffee, such as the fruity and earthy El Gallo breakfast blend, as well as custom American-made bicycles.
Take in the sights on the Magnificent Mile, but skip the brands you can shop at home. Just two blocks off Michigan Avenue, SPACE 519 (200 E Chestnut St.) is a curated concept shop that’s right at home in its Gold Coast surroundings. Inspired by the travels of well-heeled owners Lance Lawson and Jim Wetzel, the offering includes women’s apparel, men’s accessories, and home goods you won’t find anywhere else.
Head west to check out the hip record stores and boutique shops in Wicker Park. There, you’ll find Big Star Tacos (1531 N Damen Ave.) in a defunct 1940s gas station. Turns out, a rock and roll soundtrack, authentic Mexican street food, and margaritas is all it takes to transform any space into a cool hangout.
And you can’t miss two of the city’s most famous tourist attractions. At The Art Institute of Chicago (111 S Michigan Ave.) search out world-famous works, such as “Nighthawks” by Edward Hopper, “A Sunday Afternoon on the Island of La Grande Jatte” by Georges Seurat, and “The Old Guitarist” by Pablo Picasso. Right next door in Millennium Park, snap a selfie at the iconic “Cloud Gate” (201 E Randolph St.), the famous mirrored sculpture known as “The Bean.”
Italian in spirit, the menu at RPM Italian (52 W Illinois St.) features pasta, steak, and fish, which are served in a spacious, Milan-inspired setting. Come for aperitivo hour, when light bites, wines, and cocktails are just $5, $7, and $8, respectively. Or stay for dinner, which may start with grilled bruschetta, include prosciutto service, and end with cooked-to-order bomboloni (Italian brioche doughnuts with Nutella).
Don’t leave town without enjoying the all-day breakfast at Miss Ricky’s (203 N Wabash Ave.). Whether you’re after a power-punch protein bowl or a tower of sparkling mimosas, they have you covered.
Writer: Nick Papa