What $500 Buys in Chicago

Bruce Hutchinson

In Chicago, America’s Second City, September kicks off the vibrant fall events calendar, including a jazz festival headlined by Cassandra Wilson on the 1st and the Chicago Gourmet Food and Wine Festival on the 23rd. But food is a year-round preoccupation; Grant Achatz augmented his famous Alinea with Next, a ticket-only restaurant, and The Aviary, a bar, while GT Fish & Oyster is more casual but just as delicious.

Compiled by Candice Chan and John Wogan

A two-night stay along the Gold Coast at Public, launching this month by the ubiquitous Ian Schrager. The 285-room property aims to reinvent the hotel concept by offering high-end services that focus on quality over quantity—meaning less superfluous offerings and a more all-inclusive experience (and price). publichotels.com.

A birdhouse crafted from salvaged barn wood by artisan Eric Erf and an “upcycled” plywood bench to set it on by owner Arrin Williams at the three-month-old Haymaker Shop, devoted to sustainable furniture made in the Midwest. haymakershop.com.

A three-course feast for ten—served at a communal table and featuring dishes like scallops with sunchoke, asparagus and salmon roe—at GT Fish & Oyster. Headed by prominent Chicago chef Giuseppe Tentori, the new, sleek and perpetually packed seafood spot is from the group behind last year’s breakout eatery, Girl & the Goat. bokarestaurantgroup.com.

Three tickets and four handcrafted chess sets at the Art Institute of Chicago. Both the Indian Art of the Americas and the African Art galleries just reopened after renovations, with 550-plus pieces—like a textile woven from the thread of Golden Orb spiders—currently on display. artic.edu.

Three Maude’s Plateaux shellfish towers and five signature Smash cocktails at Maude's Liquor Bar, an eight-month-old industrial-chic speakeasy from the owners of local fave Gilt Bar Chicago. maudesliquorbar.com.