A while back I posted Toronto: A Million Skyline Looks, which highlighted some of my favorite shots in Canada’s biggest city. I recently re-read the post and it inspired me to start a series of posts highlighting what my camera has shot while hanging out in a big city. Next up the Windy City and the million skyline looks it has to offer!
Chicago is one of the biggest cities in the United States, home to one of the most impressive and beautiful skylines you will find anywhere. I’ve spent a lot of time there over the years, being not to far from home. Below are some of the favorite Chicago skyline photos I have taken, so far that is. π

Always keep an eye on Chicago’s tall buildings when along the water.

The city view from Shedd Auditorium opposite Lake Michigan.

The panoramic skyline sits beyond the morning snow and frost of North Street Beach.

Looking south from North Street Beach.

Sand, lake and skyline from Ohio Street Beach.

Skyline views await walking either side of Navy Pier.

Looking west from N. Lake Shore Drive at the buildings that line both sides of the Chicago River.

Dine to these views at the Pump Room, up-top the Public Chicago hotel.

Capture the hustle-and-bustle of Chi-town from the 26th floor and Vertigo Sky Lounge.

Capture the Windy City at sunset from up-top at Vertigo Sky Lounge.

You never known when that next Chicago city shot will present itself, more from up-top Vertigo Sky Lounge.

Capture the heart of the Windy City from the 26th floor and Vertigo Sky Lounge.

Capture the heart of the Windy City from the 26th floor and Vertigo Sky Lounge.

Up-top Vertigo Sky Lounge. You can tell it’s a favorite spot to capture the city.

Views looking northward from the Hyatt Regency Chicago.

Make sure to look northward when walking along E. Upper Wacker Dr. in the Loop.

The heart of Chicago sits beyond Buckingham Fountain.

Plenty of skyline views to be had in Grant Park.

Willis Tower and the skyline are peaking through the trees in Grant Park.

Looking north from a pedestrian bridge in Grant Park.

Walking northbound along Michigan Avenue as you are about to cross the Chicago River.

Early morning from the south side of Navy Pier.

Night time views up-top the John Hancock building at 360 Chicago.

Majestic views up-top the Sears Tower, I mean Willis Tower.

Capturing the tall buildings randomly as a camera holding car passenger. π

Capturing the tall buildings randomly as a camera holding car passenger. π

Reflecting on the city at The Bean in Millennium Park.

Night time city shot from Lake Michigan.

Make sure to always look up when walking in a big city. Random shot while walking the streets.
What other spots would recommend for capturing the Chicago skyline and heart of the city?
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