15 Photos That Prove You Really Must Visit Chicago at Night

The Chicago Theatre
The Chicago Theatre | © Neal Khalawara/Unsplash

Chicago is a beautiful city at any time of day, but when the sun goes down, it truly comes alive. Streets pulse with electricity as crowds spill out of rowdy, neon-lit bars and restaurants. An elevated train noisily chugs along above rushing commuters as runners and cyclists try to weave among the hordes. And all the while, the city begins to glow with the light of over one hundred skyscrapers and hundreds of other high-rises standing brightly against the night sky.


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.

Chicago sunset
Sunset silhouettes
Looking north from the John Hancock Center

Skyline views

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.

Nighttime skyline
The John Hancock Center
From the south

Looking down

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.

The densely packed area around the Chicago River
Looking south from the John Hancock Center
Looking down on the Loop

Looking up

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.

The Chicago River
From the DuSable Bridge
The river
River North


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.

The Chicago Theatre
The famous Billy Goat Tavern

Culture Trips launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes places and communities so special.

Our immersive trips, led by Local Insiders, are once-in-a-lifetime experiences and an invitation to travel the world with like-minded explorers. Our Travel Experts are on hand to help you make perfect memories. All our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

All our travel guides are curated by the Culture Trip team working in tandem with local experts. From unique experiences to essential tips on how to make the most of your future travels, we’ve got you covered.

Culture Trip Spring Sale

Save up to $1,656 on our unique small-group trips! Limited spots.

Edit article