After sharing our best locations for cityscapes in Chicago, we thought we’d come back with the best rooftop locations. Elevated views are always great and Chicago has a lot of options to get something a little different!

Let’s start with the obvious observations deck. Chicago has two observatories that are open year-round: 360 Chicago and the Skydeck. The downside of these locations is that you have shoot through glass and regular tripods are usually not allowed.

Located at the top of the Willis Tower, the Skydeck is the highest location on our list. It has great views of the downtown are to the north.

The view to the west is also interesting at night, with the streets going all the way to the horizon.

360 Chicago is located at the top of 875 North Michigan Avenue (formerly John Hancock Center). It’s our favorite observation deck, with great views along Michigan Avenue. They have Tripod Mondays when they allows tripods all day on Mondays.

The lake views are fantastic as well and in the late afternoon, you can get some nice shadows on the lake, especially in winter.

Now, let’s go over rooftop bars and restaurants. The one we list in this post will let you shoot, sometimes with a tripod. We recommend you at least get a drink before shooting, it’ll make the experience easier and more enjoyable 🙂

First stop: the Cityscape Bar at the Holiday Inn Chicago Mart Plaza River North. It has great views down the River, but hurry up, they won’t last, as they are building a couple of towers in front of the hotel.

Next, Cindy’s rooftop. It has great views over Millennium Park and the Lakeshore East. It’s perfect at sunset and dusk!

London House is a more recent addition to Chicago’s rooftops. Located along the river, it’s a great spot but they won’t let you shoot unless you order something. Given the location, it’s not the worst thing in the world to get a drink there!

Our last stop is Terrace 16 at Trump Tower, just across the river from London House. You get the views east towards the lake.

Did we miss any other Chicago rooftops? Let us know in the comments!