High & Mighty: Chicago's Best Rooftop Bars

364 W Erie St, Chicago, IL 60610 (map)

There's nothing fancy about this River North bar, from its American-style bar food (wings, burgers, pizza) to its pared-down decor. But who cares about fancy trappings when there's a 5,000-square-foot outdoor area including a rooftop deck? Obviously not the swarm of after-work partiers who pack the place when warm weather hits.

1113 W Randolph St, Chicago, IL 60607 (map)

At first glance the first-floor dining room, slick bar and patio beer garden may seem like the preferred hangout spots, but insiders know to head to the third-floor rooftop deck with its cabanas and cozy nooks. Pair the panoramic downtown views with creative twists on American cuisine and sparkling cocktails, and everyone's a winner at this trendy West Loop sports bar co-owned by White Sox General Manager Kenny Williams.

201 N State St, Chicago, IL 60601 (map)

The name may be basic enough, but that's the only thing that is at this gorgeous 7,000-square-foot outdoor/indoor lounge on the 27th floor of the Wit Hotel in the Loop. Relax on double-side settees or grab a spot at communal tables (some with built-in fire pits) as you take in the downtown scenery, nosh on Italian small plates and sip creative cocktails like the hibiscus margarita. For the most dramatic views of Millennium Park, opt for a spot at the eight-top table that sits on an extension protruding 12 feet from the building's edge.

2 W Erie St, Chicago, IL 60610 (map)

Disoriented? Eyes playing tricks on you? You must be on the 26th floor at this penthouse bar in River North. Dazzling options, such as the 1,000-square-foot outdoor patio, exotic Asian dishes, wrap-around glass windows and roving cocktail carts will do that to a person. Our favorite remedy: one of the flavorful cocktails, like a Singapore Sling or mojito. And if those don't bring a smile to your face, perhaps the plush leather couches, cat suit-clad servers and retro flicks playing in the indoor bar area will.