15 Photos That Prove You Really Must Visit Chicago at Night

The land around Chicago is incredibly flat, which results in some amazing light at dusk as the sun slowly drops to the horizon to the west of the city. Seeing the sunset from the top of a tall building is always a good idea, but it’s also hard to beat seeing the skyline in silhouette against the golden orange and pink hues of the sky.

Finding a vantage point outside of the Loop allows you to take in Chicago in all its glory, and there are many great places to do it. Some of the best include the view from the Adler Planetarium at Museum Campus and the Centennial Wheel at Navy Pier, but anywhere that the land juts out along the Lakefront Trail should have spectacular views of downtown.

The density and variety of the buildings in Chicago can only be fully appreciated by looking down on it all. The Skydeck on the 103rd floor of the Willis Tower has breathtaking views of the Loop from the south, while the John Hancock Center offers similarly amazing sights that you can enjoy with a drink or a meal at the 96th-floor Signature Lounge. Push yourself by stepping out onto The Ledge at the Willis, or trying Tilt at the Hancock. Neither are recommended for the faint-hearted.

It’s equally impressive looking up, as you try to comprehend the sheer scale of the buildings while surrounded by the buzz of the city and the light reflecting off the river or the lake. Walking around the Loop and River North, where the tallest buildings are tightly packed in, enables you to get up close to Chicago’s most impressive buildings. Admire the brightly lit Art Deco detailing of buildings such as the Carbide and Carbon Building and the Merchandise Mart along with the modern twists of Aqua’s famous rippling balconies.

Once you’ve admired the scenery outdoors, it’s time to head indoors. It’s not just the tall buildings that light up at night, as the city’s institutions, including the Chicago Theatre, Green Mill Cocktail Lounge and House of Blues, turn on their signs. Remember, no authentic Chicago bar is complete without neon beer signs in the window.