The boutique Handle with Care (1706 N. Wells St.; 312-751-2929, handlewithcareboutique.com) lures Old Town Art Fair revelers June 9 and 10 with a 10 percent discount on all in-store merchandise, including clothing from J Brand, Paige Denim, and Rebecca Taylor, and an extra 50 percent off sale items.

Scope second-time-around decor, clothes, and jewelry from more than 150 vendors at The Vintage Bazaar, a market that convenes from 12 to 5 p.m. on the second Sunday of every month. The action, once at Congress Theater, moves June 10, when the Aragon Ballroom (1106 W. Lawrence Ave.) becomes the bazaar’s home base.

The Nordstrom half yearly sale for men (nordstrom.com for locations) kicks off June 15 and runs through June 26.

Attention brides-to-be: Erin Gallagher’s Gem Bar (1013 W. Webster Ave.; 312-492-7548, egjewelry.com) offers a deal June 8 through 16 designed for buying bridesmaids’ gifts. Get 20 percent off one necklace, bracelet, or other bauble; 25 percent off two to four; and 30 percent off five or more.

What might convince a fashion fan to cross party lines? Catching a glimpse of Vogue’s Anna Wintour, who comes to town June 12 with the model Chanel Iman to host the political pop-up shop Runway to Win at Harpo Studios (110 N. Carpenter St.). Tickets (from $150) are required for the event, which will raise funds for Barack Obama’s campaign with swag designed by the likes of Marc Jacobs, Diane von Furstenberg, and the team behind Proenza Schouler. Prices for items such as Obama-themed bags, shirts, and scarves run from $40 to $95.

Photography: Courtesy of vendors