Kaela Davis broke a 106-all tie on a layup with 2:10 remaining in the second overtime. Theresa Plaisance's layup with 1:11 left made it 110-106.

Diggins-Smith, who also hit a 3-pointer to force double overtime, sealed the win by making two free throws with 29 seconds left.

Davis scored 23 points, Karima Christmas-Kelly had 17 and Glory Johnson totaled 12 points and nine rebounds as the Wings (10-11) snapped a two-game losing streak.

Stefanie Dolson had 26 points and 10 rebounds, Jessica Breland added 23 points and Allie Quigley eclipsed 1,500 points for her career with 22 for the Sky (6-13).

Chicago entered the game with the WNBA's longest winning streak.

The Sky clipped the Wings 90-84 in their first of three meetings this season on Wednesday.

Dolson's two free throws with 8.3 seconds left in the first overtime gave Chicago a 102-99 lead before Diggins-Smith's 3-pointer with 3.4 seconds left tied it.

Dallas pulled within 66-63 entering the fourth quarter. Chicago did not trail in the game until Johnson's layup made it 81-80 with 2:35 to play.

Dolson put the Sky up 87-85 by making two free throws with 11.8 seconds to go, but Kayla Thornton's layup with 4.1 seconds left tied it.

Chicago led 44-39 at halftime.

With 2:05 left in the first quarter, Quigley scored her milestone 1,500th point on a jumper. She scored 14 of her team's 22 points in the first period as the Sky opened a six-point lead.

Chicago continues its four-game road trip against the Seattle Storm on Tuesday. Dallas visits the Western Conference-leading Minnesota Lynx on Wednesday.