Temecula and Chicago Outings From Winery Tapas to Dart Lounges

4.3 (231)

41150 Via Europa, Temecula, CA 92591, USA

Traditional tapas and Mediterranean-inspired plates bring Spain to this Temecula wine country restaurant. Its patio doubles as a dining area and wine tasting spot with frequent live music. Tapas Tuesday happy hour runs 5:00 PM to 8:00 PM, and parties of six or more call ahead.

39730 Calle Contento, Temecula, CA 92591, USA

A vineyard-view patio anchors this modern Temecula winery, linking wine tasting to the surrounding landscape. Live music runs on a steady weekly schedule, outdoor wellness sessions use the grounds, and wine and food purchases are separate from patio access and music events.

4.6 (121)

430 N Michigan Ave

Beside the bridge on the north side of the Wrigley Building, this flag-lined Chicago square serves as a landmark gathering space and tour meeting point. Public art draws people in, and walking close to the tall surrounding buildings gives shelter from the wind.

3.8 (448)

Wed – Fri, 17:00 – 02:00 (+1); Sat, 17:00 – 03:00 (+1)

113 W Hubbard St

Three bars, a DJ setup and dart boards fill this wide Hubbard Street lounge in River North, open Wednesday through Saturday until 2:00 AM, or 3:00 AM on Saturday. Craft cocktails come at mid-range prices, and a dress code applies at the door.