The 14 Best Outdoor Rooftops in Chicago

When it comes to dining and drinking, the view is almost always better from the top. That is especially true in Chicago, where rooftop vistas often frame Lake Michigan or the Chicago Riverwalk. Or, you might be shoulder to shoulder with high-rises and some of the world’s most amazing architecture, from gleaming and sleek towers to Art Deco-era wonders.

Chicago’s rooftop bars, lounges and restaurants aren’t just open at night. You can just as easily linger over fluffy omelets at brunch or meet friends for a lunch of lobster rolls as you might cozy up by the terrace fire with a cocktail and watch the sunset. Many of these venues are perched atop hotels, but some are also carved into a restaurant’s decor, providing a fresh vantage point come warm weather.

In recent years, more and more rooftop spaces have opened, proving that these are the places to be seen. From empanadas and pisco sours at...