This outpost of the British boutique hotel chain blends co-working and hospitality. During the day, the lobby’s midcentury-modern couches fill with folks tapping at laptops. Labor segues into drinks in the basement bar or a meal at Cabra, a Peruvian-inspired rooftop restaurant reached via elevators lined with antique city maps. Most of the 182 rooms skew small, albeit with big, factory-style windows. Guests partake in yoga flow classes, literary salons and workshops on digital philanthropy.

Occupying two stories of the former Free Methodist Publishing House (built 1909), the luxurious, loft-like Publishing House B&B offers 11 rooms adorned with vintage oriental carpets, company safes and steamer trunks. Ample breakfasts, which might include homemade Ligurian olive oil cake and gluten-free doughnuts, live up to the district’s foodie reputation.

Convenient for lunch and with a Sunday Jazz brunch, the 50,000-square-foot Time Out Market serves as a culinary tour of Chicago with 11 eateries and bars created by accomplished restaurateurs from across the city. Options range from artisanal chocolates to Michelin-starred plates; try the hefty fried chicken sandwich from Cleo’s Southern Cuisine.

Staff at J.P. Graziano, including the founder’s great grandson, patiently talk newcomers through all the sandwich permutations at this family-run grocery, on the premises since 1937. The signature Mr. G sub combines artichoke hearts, provolone, three Italian meats and a modern touch: truffle mustard.

Rest your feet and satisfy a sweet tooth with a tasting flight on the patio at Cone Gourmet Ice Cream; the ever-changing flavor menu might include blueberry chip, Guinness and Netflix n Chill (buttered popcorn flavor with M&M’s).

“Top Chef” winner Joe Flamm opened his debut restaurant, Rose Mary, in April and diners still need to book two months in advance to try the Italian-Croatian cuisine highlighted by beef burek and pork ribs pampenella.

Michelin-starred chef Curtis Duffy has refreshed his blowout 8-10 course tasting menu at Ever Restaurant, serving intricately constructed dishes at reverentially lit tables.

Grant Achatz, Chicago’s best-known gastronomist—famous for dishes set atop deflating lavender-scented pillows—oversees the Aviary cocktail lounge, where “performance-forward” beverages might seep smoke or come served in a porthole-shaped cold-infusion decanter.

The members of bands playing Chicago’s Pitchfork, Riot Fest and Lollapalooza music festivals often schedule late-night sessions at Bottom Lounge, a year-round beer and live music venue beneath the Lake Street L track.

M2057 by Maria Pinto is the Chicago designer’s showroom for women’s ready-to-wear; clients include Michelle Obama. The look is flowing, asymmetrical, the Italian stretch fabric not just cool and comfortable, but wrinkle-resistant, machine-washable and quick-drying—suited for work, travel and all body types.