Having grown up in the suburbs of Chicago and then living in the city proper for a decade, it was only a matter of time. I had to do an epic photoshoot with dogs in front of the iconic skyline. That time finally came this fall.

In early September I started off at Shutterhound.  A glittery, neon-lit photography conference in Las Vegas, starring our favorite subject: pets. I heard presentations from pet photographers I’d admired for ages. I caught up with lots of old friends from past workshops and retreats together. I’d finally meeting some whom I’d known through internet coaching circles, in person. And all I wanted to do after was sleep for a month. BUT I COULDN’T.

I had to put to use, all the inspiration I’d absorbed amongst the over-stimulation of casino bells and too many cute puppy showgirls to count.

So I decided to add a leg to my trip and swing “home” to Chicago before heading back to my own pups (and husband…) in Milan.

Over the years I’ve dropped pins around the city when I’d come across a lovely backdrop that screamed “put a dog there!” I quickly noticed a trend developing. A lot of them featured the architecturally revered Chicago skyline. 

So mid-Vegas, between scribbling down notes on recognizing when a dog’s had too much and how to get over yourself and just write the damn book already, I decided to put up a model call. I had such good feedback I had to close my add after FOUR DAYS! I’d only intended to do 3 sessions but I had so many cute applicant images that I bumped it up to 8!

I had one goal in mind: dogs in front of that magnificent skyline!

Here are 3 top locations to photograph your dog with the iconic Chicago skyline as your backdrop:

1: Milton Lee Olive Park (pretty much Ohio Street Beach)

I’m embarrassed to admit this but I did NOT know about this view until I was today years old. When I visit Chicago I usually crash at my parents’ place in Streeterville. In the summer, I’ll swim, rain or shine, warm or cool at Ohio Street Beach. It’s one of my favorite things to do while I’m in town. But I’d never taken the time to just…keep walking along the water! #judged

This was the first place I wanted to photograph for this project and Remy and his mom Charlene were down. And they both have great hair, what’s not to love?!

This was an early sunrise session, even though the sun would be behind me. I’d hoped to get the buildings drenched in that juicy first-light orange glow. But nah. Chicago gotta Chicago and I got cold and rainy instead. But it’s that moodiness and change of the weather at the drop of a slice of deep dish-sauce side down, that I love most about this city. Plus Remy has such a sleek stare, the vibe was spot on.

I also had little puppy Rambo join in on the action. He was only around 4 months old at the time and such a wiggly poser! We walked around and got some shots around Ohio Street Beach in the park. Note: dogs aren’t allowed on the beach proper, but there are still plenty of ways to capture the water and the skyline like I did here. Between the steps along Lake Shore Drive where you can sit and listen to the white noise of the city, the park to catch some shade under the trees and enjoy art sculpture installations, to Caffe Olivia right on the lakefront bike path, you’re sure to have scenic options galore here.

2: Lincoln Park (park! – not neighborhood!)

This was another sunrise session but the early morning skies were more cooperative this time.

Apple, the long haired dalmatian (again….I’m a sucker for good hair), came first. Apple wasn’t a fan of car rides so when they arrived she needed some play time from mom to shrug off the doom of the drive. But she warmed up quickly. We got some great shots of her in the grass in the park with a  magnificent sky behind her.

Charlie showed up next and we got some lovely shots in a unique structure. He posed in Studio Gang’s wood pavilion that perfectly frames the north-side view of the city. Some say it’s a great place for weddings, but I vote “backdrop for dog photoshoots” all the way!

3: The Loop

If you’re into the famous architecture that dapples its way across the city, the Loop can make for a great backdrop for a photoshoot with your dog.

For this shoot we got little baby Vienna the 4 month old dachshund to strut those shortie legs around town. Here we have iconic marquees that literally scream “Chicago!” like the Chicago Theater. The grungy urban vibe emerges from the supports of the El circling overhead. And small, boutique cafés (Petterino’s) that sparkle in the fading light at dusk. Vienna certainly knows how to dress the part for each unique look!

We also have the fairly new-ish Chicago Riverwalk. It used to be a dumping ground for gangster victims, but now it’s a trendy collection of patios where you can enjoy a bite and a drink with your pup while you bork at party rental boats and kayaks floating by. This good girl Maizy was appropriately rocking her beach waves despite the fact no swims were involved.

On the other side of Michigan Avenue you have Grant Park. Here, there’s only a small part that allows dogs, so be mindful of where you are. They must be on-leash always. There’s an off-leash dog park at the north corner of 9th st and Columbus (Grand Bark Park). However! The views are postcard worthy here. Apollo came along to show off this side of town (leash removed in post!). As the city stretches up to the sky behind him, as his tongue stretches towards my pocket full of string cheese. Together it’s a gorgeous show of what both have to offer!

Finally, we stopped over by Wrigley Square to get this portrait of Julien at the Millennium Monument, with its Roman Doric-style columns (woah did that bring me back to my art history days!) to really show off his preppy, scholarly side. Note:  only service dogs are allowed in Millennium Park and security was actively enforcing that.

The “Chicago Skyline” IS the iconic diamond (some say “lady-bits”) shaped top of the Crain Communications building, to me. So it should be utilized in a skyline shot as much as you can, in my professional opinion.

So next time you’re in Chicago with a pup or two in tow, you know where to go. Swing by one of these places for a photoshoot featuring your happy dog mingling with the sparkling Chicago skyline.

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