Chicago Photography Guide Part 1 - The Classics

Chicago Photography Guide Part 1 - The Classics

Chicago Willis Tower Sears Tower Cloudy Reflection City Illinois

Written and Photographed by Mike Lindle


Heading out to Chicago but don’t know where to shoot? After recently exploring the city for 2 months paired with a few visits over the years, I have put together a 4 part series on the best photography locations in Chicago:

Part 1 - The Classics

Part 2 - Waterways & Boats

Part 3 - CDOT Trains & Parking Lots

Part 4 - Alt Chicago

I’ve also included a few tips, the gear I used, and how to get to each location through Google Maps!


The Bean (Cloud Gate) - Millennium Park

The Bean sits right on the edge of Millennium Park in Chicago. Artistically, the sculpture is called Cloud Gate, but the locals insist that it’s The Bean. Designed by Anish Kapoor in 2006, the design was inspired by liquid mercury. The structure stands at 33 feet high and tourists love snapping their photos in the reflection of the sculpture.

Chicago The Bean Cloud Gate Cloudy Reflection City Illinois
Chicago The Bean Cloud Gate Cloudy Reflection City Illinois

Cindy’s Rooftop Bar (The Bean Overlook)

Sitting at the top of the Chicago Athletic Association and a Shake Shack is Cindy’s Rooftop Bar. With the best views of Millennium park from above, this spot shuold definitely stay on your list. They typically don’t allow photos taken by professional cameras (interchangeable lens cameras) without a photo pass. You can contact them in advance to get one. No time to plan ahead? You can probably take a few photos if you’re quick and sneaky before they ask you to put your gear away.

  • Pro Tip - Visit their deck when the lighting is good, it stays open in winter!

  • Cost - Free, but you should probably buy at least 1 beer/cocktail to not overstay your welcome. ($7-$13)

  • Camera - Nikon D750

  • Lens - Nikkor 12-24mm f/4G

  • Location

Chicago Cloudy Reflection City Illinois Cindys Rooftop Bar View of The Bean Cloudgate

The Chicago Theatre Sign

Originally known as the Balaban and Katz Chicago Theatre, The Chicago Theatre is the city’s landmark theatre. Built in 1921, the Chicago Sign hanging off this theatre has been a destination for many tourists. Still active, try to budget some extra time to see a performance!

  • Pro Tip - Check it out in the snow or after sundown when they turn on the lights!

  • Cost - Free and Public Exterior (Ticket Prices for Shows Vary)

  • Camera - Nikon D750

  • Lens - Nikkor 35-70mm f/2.8D

  • Location

Chicago Cloudy Reflection City Illinois Chicago Theatre Theater Night Chicago Sign

Willis (Sears) Tower Lookup

Walking around the Chicago Loop, you will be surrounded by some of the US’s largest sky scrapers. Even as a New Yorker, you’ll still be tempted to look up and enjoy some of the sweeping views straight above. One of the best sites I’ve found is staring straight up at the Willis (Sears) Tower on a foggy day, as the building disappears above. Completed in 1973, it held the record for the tallest building in the world for nearly 25 years (taking the title away from the World Trade Center’s Twin Towers in New York). It remained the tallest building in the Western Hemisphere until New York’s One World Trade Center was completed in 2014.

Chicago Willis Tower Sears Tower Cloudy Reflection City Illinois
Chicago Willis Tower Sears Tower Cloudy Reflection City Illinois

Willis Tower “The Ledge” and Sky Deck Observatory

Sitting at 103 stories above the ground, it is one of the tallest observation decks in the United States and is easily one of Chicago’s most famous tourist attractions. Approximately 1.7 million tourists visit annually. All times of day are epic, try to come around sunset or low fog conditions for best visuals.

  • Pro Tip - Make sure to snag a selfie standing over the glass on “The Ledge”, like this stranger pictured below! The floors are glass so you can see straight to the bottom.

  • Cost - $25

  • Camera - Nikon D750

  • Lens - Sigma 14mm f/1.8 Art

  • Location

Chicago Willis Tower Sears Tower Cloudy Reflection City Illinois Sky Deck Sky Box Selfie

Chicago Board of Trade Center

Built in 1930, this skyscraper is another classic Chicago landmark (designated on May 4th 1977). It is currently an active office building housing employees of the CME group as the primary trading venue for the derivatives exchange. It is a Chicago emblem of preserved Art Deco style, with a three-story art deco statue of Ceres, Goddess of agriculture, at the top. Makes sense for Illinois’ vast grain fields surrounding Chicago.

Chicago Board of Trade Center Cloudy City Illinois Foggy Clouds

The Wrigley Building Sky Walk

The Wrigley building was built in 1924 to house the corporate headquarters of the Wrigley Company. It was the first office building constructed on the North side of the River. Sold to investors in 2014 and again in 2017, it now houses modern amenities on the ground floors such as a gym and a Walgreens.

  • Pro Tip - Step into the plaza between the two towers and look up to see the Sky Walk connect the two buildings at the 14th floor

  • Cost - Free and Public View

  • Camera - Nikon D750

  • Lens - Sigma 14mm f/1.8 Art

  • Location

Chicago Cloudy Reflection City Illinois Wrigley Building Sky Walk Sky Bridge Trump Tower Night

John Hancock Center

Located in the Magnificent Mile part of the city, this 100 story skyscraper looms over many surrounding buildings. When it was completed in 1968, it was the 2nd tallest building in the world, and tallest outside of NYC. To this day, it contains the 3rd tallest residence in the world, after the Burj Khalifa in Dubai and the Trump Tower in Chicago. When caught in the right lighting conditions, this building is a great site!

Chicago John Hancock Center Cloudy City Illinois Magnificent Mile Lookup Wide
Chicago John Hancock Center Cloudy City Illinois Magnificent Mile Lookup Wide

The Tiffany Dome - Chicago Cultural Center's

Located in the Chicago Cultural Center you’ll find the world’s largest Tiffany glass dome. Before Tiffany&Co made jewelry, the company was best known globally for its decorative glass. Originally built as Chicago’s first public library in 1897, Chicago eventually converted the building into the Chicago Cultural Center, offering tourists free history and context during their visit to Chicago.

Chicago Cloudy Reflection City Illinois Tiffany Dome Chicago Cultural Center
Chicago Cloudy Reflection City Illinois Tiffany Dome Chicago Cultural Center

Crown Fountain - Millennium Park

Sitting right on the edge of Millennium Park in Chicago, a stone’s throw from The Bean is Crown Fountain. Designed by Jaume Plensa in 2004, the design features both scenery and local residents, sometime even spewing water from their mouths as part of the fountain display. The structure stands at 50 feet high and tourists love visiting in summer to play in the water.

Chicago Crown Fountain Cloudy Reflection City Illinois

Next Time:

Hard Rock Hotel Skyline View

Signature Room 360 Chicago - John Hancock Center


If you enjoyed this, check out Focal Collective’s other content on the Focal Points section of our website. Feel free to look through our Artist Interview Series as well!

Road Trip Photography - The Iceland Experience

Road Trip Photography - The Iceland Experience

Superbloom at Lake Elsinore - Poppy Apocalypse

Superbloom at Lake Elsinore - Poppy Apocalypse

0