The Robey Chicago​: Located in a Chicago Landmark District, Wicker Park, this art deco skyscraper was designed in 1929 as an office building. In the 1980’s it transformed from housing professionals to artists who called it the Coyote because its silhouette resembled a howling canine. Now, as a hotel, the interiors have a very cool mid-century modern vibe, for the best views select a corner suite overlooking Milwaukee Ave. For 180-degree views of the skyline, visit the rooftop Cabana Club. (NL)

The CAA,​ Chicago Athletic Association Hotel: Once a private men’s club, this Venetian Venetian Gothic building by Henry Ives Cobb on Michigan Ave, is now open to the public. Its extravagant exteriors, modeled after the palace of the Doge in Venice, features fin de Siecle styled interiors with sporting motifs. The traditional Drawing Room in the second-floor lobby has table service, while the contemporary Cindy’s on the roof boasts excellent views of Millennium Park and Lake Michigan. (NL)

Estereo: Logan Square has a ton of cocktail bars, but my favorite is Estereo​ ​at the corner of Milwaukee and Sacramento. Perfectly mixed cocktails and the bartenders also spin old school vinyl. The bar occupies the center of the room for great people watching. Paulie-Gee’s across the street makes delicious Detroit style pizza –vegan available!. (NL)

Cafe at the Humboldt Park Boat House:​ This cafe makes our list for the setting alone – seating is available on a beautiful terrace overlooking the Humboldt Park Lagoon. The lagoon recently made the news because of a new and temporary resident somebody let loose in the park, an errant alligator affectionately named Chance the Snapper. Now that Chance is safely at home on a Florida alligator farm, rent a swan boat, and have a glass of wine on the terrace afterward. (NL)

Floating World Gallery:​  An outstanding resource for Japanese prints and paintings in all genres Ukiyo-e, Meiji, Shin Hanga, Sosaku Hanga, and Contemporary. Or for something to memorialize your Chicago visit with an oil portrait by a local artist. You can’t beat the prices offered by Casey Despot for oil paintings on canvas. (NS)

Jayson Home:​ This place a must-stop Chicago shop for new and old home furnishings, accessories, and gifts. With skylights and plants strewn throughout, the venue has an open loft vibe. (AF)

Second Presbyterian Church: Second Presbyterian Church: ​This​ landmark Gothic Revival church is a must-see for it’s impressive English Arts and Crafts interior and monumental sized windows including nine by Tiffany Studios. Two smaller windows designed by Edward Burne-Jones are the only example of the Pre-Raphaelite artist’s stain glass work in the midwest. After taking the free docent-led tour at Second Presbyterian, check out the Glessner House Museum nearby. (NS)

The Oriental Institute:​  An often-overlooked museum cram-packed with artifacts from the Mideast. The spoils from the University of Chicago’s archaeological digs in that part of the world. The collection includes a panel from the Processional Way that led to the Ishtar Gate. While in Hyde Park, check out the recently restored Robie House, one of the best of Frank Lloyd Wright’s Prairie-style homes, and recently inducted into the list of UNESCO World Heritage Sites. (NS)