Date Night in Chicago

Elephant & Castle

Chain with a British pub feel serving beers on tap & classic fare, such as fish ’n’ chips.

TNT Rooftop Restaurant

Drunk Shakespeare Chicago

Metro

A variety of indie & alternative bands play at this popular, intimate concert venue.

Emporium Arcade Bar

Decades of games, dozens of beers & 60-plus whiskeys in a loft-like setting with vaulted ceiling.

The Vic Theatre

Century-old 5-story vaudeville theater (with 3 bars) that features live music & cult/classic movies.

Bottom Lounge

Venue for underground music, beer & casual American comfort food (including vegetarian options).

Monteverde Restaurant & Pastificio

Stylish spot serving refined, contemporary Italian fare such as fresh pastas, plus global wines.

ROOF on theWit

A summer hotspot on the 27th floor of theWit Hotel, with skyline views & upmarket cocktails.

Piccolo Sogno

Rustic Italian fare, including pizza from a wood-burning oven, a vast wine list & garden seating.

Lucky Strike Chicago

Sprawling arcade bar featuring gastropub eats, cocktails & mini-golf in steampunk-themed digs.

Puttery

Laugh Factory

Well-known comedy club for seasoned & emerging stand-up acts, plus surprise celebrity guests.

Swift & Sons

Swanky, sprawling spot featuring premium steaks & seafood, plus a bi-level bar & house concierge.

Gus' Sip & Dip

WhirlyBall

Lively amusement center featuring WhirlyBall, bowling & laser tag, plus a sports bar.

Centennial Wheel

Cupitol Coffee & Eatery (Streeterville)

Easygoing bar/eatery serving cafe fare such as sandwiches, salads & baked goods, plus coffee & tea.

Concord Music Hall

Mid-size concert venue supporting a variety of genres, including hip-hop, indie rock & dub step.

AMBAR Restaurant, Chicago

Small plates menu of traditional Balkan dishes, plus regional spirits, offered in rustic-chic digs.