Windy City Wine Festival
Featuring more than 300 varietals from around the world, this vino celebration is a fitting cap to summer festival season, with live music, signature dishes from local restaurants and more. Proceeds benefit the Chicago Parks Foundation.
Time: 5-10 p.m. Friday,
3-8 p.m. Saturday
Place: Buckingham Fountain, 301 S. Columbus
Cost: $45-$90 in advance, $50-$120 at the door; $15 designated driver. For tickets, visit Windycitywinefestival.com.
Fall Gallery Walk
The River North Design District presents its fourth annual event in partnership with more than a dozen galleries and showrooms, each displaying the work of a top visual artist and a vignette from a local designer — think Eric Gushee and PROjECT. interiors, Linc Thelen and Blutter Shiff Design Associates and more. The night kicks off with a party at Jesse Chicago (745 N. Wells).
Time: 5-9 p.m.
Place: various locations
Cost: Free. For a full list of participating galleries, visit Rivernorthdesigndistrict.com/fall-gallery-walk.
Chicago Men’s Fashion Awards
The Costume Council of the Chicago History Museum pegs its 10 best-dressed Chicago gents at this third annual celebration of style. Hosted by Eric Himel and Darlene Hill and co-chaired by Maggie Morgan and John Rogers, the art deco-inspired event will have cocktails, light bites from DineAmic Group and more.
Time: 5-8 p.m.
Place: Room & Board, 55 E. Ohio
Cost: $75. For tickets, visit Chicagohistory.org.
Chicago House Speaker Series
Emceed by NBC reporter Chris Hush and featuring keynote speeches by comedian Wanda Sykes and figure skater Adam Rippon, this eighth annual luncheon event celebrates the LGBTQ community.
Time: 11 a.m.–2 p.m.
Place: Hilton Chicago, 720 S. Michigan
Cost: $200-$300, $500 VIP. For tickets, visit Chicagohouse.org.
Green Tie Ball
Chicago Gateway Green celebrates the 27th anniversary of its colorful black-tie affair, hosted by Candace Jordan and Nina Mariano. The night — themed Green Eggs & Glam — will be full of whimsical surprises, plus live performances by Dr. Bombay and special guest Redfoo from LMFAO.
Time: 7 p.m.-midnight
Place: The Geraghty, 2520 S. Hoyne
Cost: $175 and up. For tickets, visit Gatewaygreen.org.
River Boat Dinner Cruise
City Winery and The Duck Inn team up for a delicious end-of-summer event. After cocktails at the winery’s Riverwalk location, guests will depart on an electric boat — full of cheese, charcuterie and Champagne — and be ferried to Bridgeport, where chefs Kevin Hickey and Kris DeLee will serve up multicourse meal. Cap the night with cigars on the ride back to River North.
Time: 5:30 p.m.
Place: City Winery at the Riverwalk, 11 W. Riverwalk South
Cost: $257. For tickets, visit Citywinery.com/chicago.
Gold Coast Fashion Award Show
The dress code reads “creative cocktail” for this 63rd annual show, presented by Neiman Marcus. Hosted by the Children’s Service Board of Ann & Robert H. Lurie Children’s Hospital, the event features food stations, a cocktail reception, paddle raise, sweets shop and more.
Time: 6-10 p.m.
Place: Revel Fulton Market, 1215 W. Fulton Market
Cost: $325 and up. For tickets, visit Gcfas.com.
‘Enrico David: Gradations of Slow Release’
The London-based Italian artist’s exhibit opens today at the MCA. His drawings and sculpture — which will be on display through March 10 — explore the human form in all its many states of being.
Place: Museum of Contemporary Art, 220 E. Chicago
Cost: $15 general admission. For more information, visit Mcachicago.org.
A Sterling Event
WGN evening anchor Micah Materre emcees this 14th annual gala, benefiting A Silver Lining Foundation’s Buy a Mom a Mammogram program, which funds breast health screening for uninsured women. The lifesaving night features live and silent auctions, a cocktail hour, dinner and more.
Time: 6:30 p.m.-midnight
Place: Hyatt Regency McCormick Place, 2323 S. Martin Luther King
Cost: $300. For tickets, visit Asilverliningfoundation.org.