Harry Caray's

This upscale steakhouse couples classic dishes with a luxe vibe, featuring perfectly cooked steaks and a chic patio for cigar lovers.

Cozy, laid-back coffee shop in the Tri-Taylor/West Side serving espresso drinks and pastries.

Nestled in a breezy beach house vibe, this spot serves up California cuisine and homemade goodies, making it a must-visit for a deliciously laid-back meal.

Nestled in an art deco tower, this chic Gold Coast hotel boasts plush rooms, a rooftop pool, and stunning skyline views, perfect for a luxe getaway.

Bakery-cafe serving bread, pastries, sandwiches & cocktails in a casual space with a retro vibe.

Old-school Chicago hot dog stand serving up tamales and a variety of other hot dog specialties.

Lincoln Park venue offering sushi and sake in a classy atmosphere.

Fashionable, riverfront locale for seafood-based fine dining with pasta, steaks & premium full bar.

A beloved dive bar in Wrigley since 1951, this cozy spot serves up craft beers, darts, and good vibes, perfect for catching a game or hanging with friends.

Red & white pizzas, a handful of Italian starters & pasta dishes with wine & amaro in chic digs.