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.

Street dandies mix and match clothes from Carhartt WIP and Comme des Garçons at Notre, a boutique decorated with art and designer furniture. Friendly sales associates fluent in fashion and fragrance advise which Nike kicks to pair with, say, an Eckhaus Latta hoodie.

Interior design firm Morlen Sinoway Atelier does office and residential rehabs across the city, and its showroom is a gift and home accessories trove. Highlights: one-of-a-kind oxidized silver jewelry by Chicago-based Peter Hauschild and sculptural ceramic stacking pieces by the eponymous owner.

The Chicago Architecture Center docents discuss arcane history and building details on walking tours of the Fulton-Randolph core. The fee includes admission to the Chicago Architecture Center exhibit space—a further 25-minute walk via Lake Street and along the skyscraper-lined Chicago Riverwalk.

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