Skip to Content

The 10 Best Places to Watch the Sunset in Chicago

The 10 Best Places to Watch the Sunset in Chicago

The Windy City is known for a lot of things, from culture to sports. However, this Midwest metropolis should also be known for its gorgeous sunsets.

To make sure you get the best view possible of your Chicago sunset, here are the top viewpoints to head to.

The Best Places to Watch the Sunset in Chicago

1. Promontory Point

If you’re looking for a nice outdoor spot to catch a glimpse of the setting Chicago sun, head to Promontory Point in Burnham Park.

The area overlooks Lake Michigan, so you get the extra advantage of seeing the breathtaking view of the sun’s rays glittering on the water’s surface.

Originally the area was a landfill that was cleaned up and filled in to make this little observation area. The best part is that it’s not well-known among tourists. You’ll feel like a local and get most of the area all to yourself.

2. 360 Chicago

360 Chicago is one of the most famous observation decks in the city, however, it still deserves its spot on this list. After all, it offers views from 1000 feet up in the air on the 94th floor of the John Hancock Building.

However, during the evening hours, a lot of Chicago tourists are busy at other spots around the city. That means you likely won’t have to share the deck with too many other people.

Since this spot involves being so high up, if you’re afraid of heights, you might want to skip this one.

3. Cindy’s

Cindy’s, also known as Cindy’s Rooftop, is the place to be if you want to enjoy some drinks and food along with your sunset viewing.

The venue is located on the roof of the Chicago Athletic Association Hotel and offers coverage so you can enjoy your visit even during cold Illinois winters.

Cindy’s isn’t exactly under the radar, however, you’ll usually encounter more locals here than tourists. So, it’s the perfect spot to sit back, enjoy a cocktail, and feel like a true Chicago native while watching the sunset.

4. The J. Parker

Chicago is known for its glamorous side. So, if you’re looking for a classy place to take in the sunset, head to The J. Parker rooftop lounge.

Located at the very top of the Hotel Lincoln, this restaurant and lounge offers a swanky vibe that will make you feel like a VIP without paying a fortune first.

The roof and walls are made of glass, so you get a flawless view of the sunset all year. You also don’t have to fight too many crowds as there’s limited space for guests.

5. Lake Michigan

No list of places to see the Chicago sunset would be complete without mentioning Lake Michigan.

While it’s true that a few of our entries are located along its banks, you can’t go wrong anywhere on the Michigan lake waterfront.

The lake is a huge part of the Chicago landscape, so you have plenty of options if you’re scoping out a place to watch the sunset.

You might run into a few locals, but most tourists don’t know about this little secret. So, you can make all your friends jealous with your insider knowledge.

6. Skydeck Chicago

No trip to Chicago would be complete without a visit to the Willis Tower. Just don’t let locals hear you call it that, it’s the Sears Tower to them!

The 103rd floor of the former tallest building in the world is where you’ll find Skydeck Chicago.

Most people visit Skydeck during the daytime hours to get a far and wide view of the Chicagoland area.

However, for a truly memorable experience, go a little before dusk so you can catch the sunset from one of the floor’s glass observation boxes.

7. Navy Pier

Navy Pier is Chicago’s favorite treasure spot. Home to rides, restaurants, and eclectic shops, you can easily spend all day in this corner of the city.

However, you might not realize that the pier offers some of the best views in the city.

Located on Lake Michigan, you can get unobstructed views of the sun setting on the water from virtually anywhere on the pier.

For a really spectacular viewing experience, try to snag a seat on the Centennial Wheel. If you’re lucky, you might be at the very top during the sunset.

8. Adler Planetarium

The Adler Planetarium should already be on your to-visit list if you’re interested in space and astronomy. So, it’s fitting that it also be one of the best places to watch the sunset in Chicago.

The planetarium is on a bit of a hill, so you just have to stand outside to be treated to a brilliantly colored sky at dusk.

Though it’s a famous museum when it comes to visitors, it often loses out to other exhibits, so you don’t have to fight for a good place to watch the sunset.

9. The Signature Room at the 95th

If you want an upscale sunset viewing experience while in Chicago, you can’t miss checking out The Signature Room at the 95th.

This restaurant sits on the top floor of one of the city’s fanciest buildings and offers guests remarkable views all day.

However, for the most magical viewing experience, make reservations for just before dusk and ask for a window seat so you can see the sun setting while you enjoy your meal.

You can also try your luck seeing the sunset from the restaurant’s lounge, but that’s a bit more unpredictable.

10. Lakefront Trail

Lakefront Trail is an 18.5-mile stretch along Lake Michigan that’s a favorite spot for joggers, bikers, and those going for a casual walk in the park.

While it’s not uncommon to run into tourists and locals during the day, often people start to clear out around dusk to head home.

However, that’s when you should scope out a nice spot to relax for a while because the trail offers fantastic views of the sun setting over the lake.

However, remember, you’re in Chicago. So, if you visit in the winter, bundle up.

This site uses Akismet to reduce spam. Learn how your comment data is processed.

This site uses Akismet to reduce spam. Learn how your comment data is processed.