Cherished Family Moments at Milton Lee Olive Park

Tucked just behind Navy Pier and overlooking the iconic Chicago skyline, Milton Lee Olive Park is one of the city’s best-kept secrets for timeless, joyful family photography. With sweeping lakefront views, wide open green spaces, and a peaceful vibe that feels a world away from the bustle of downtown, it’s no wonder why this lakeside gem has become one of my favorite locations for family portraits.

As a Chicago family photographer, I know that the setting is everything when it comes to capturing natural smiles, cuddles, and laughter—and Milton Lee Olive Park delivers every time.

Why Milton Lee Olive Park Is Perfect for Family Sessions

1. Breathtaking Skyline Backdrop

Few places in Chicago offer a better view of the city than this. With Lake Michigan stretching to one side and the skyline rising on the other, it’s a striking yet serene setting for photos that blend urban edge with nature’s beauty.

2. Plenty of Open Space

The park features tree-lined walkways, wide lawns, and a peaceful fountain area—perfect for little ones to run around while I capture candid moments between the chaos and the calm.

3. Low Foot Traffic = Less Stress

Unlike other popular city spots, Milton Lee Olive Park tends to be quiet, especially during weekday mornings or golden hour evenings. That means fewer distractions for kids and a more relaxed experience for parents.

A Real Family Story

Recently, I had the joy of photographing a sweet family of five at Olive Park. The parents wanted to update their holiday photos with something more authentic and emotional—something that reflected who they are right now.

We started near the curved concrete benches under the shade trees. The kids giggled while racing down the paths, and I caught Dad sneaking in tickles during a posed shot that quickly turned playful. We moved closer to the lake where Mom wrapped her youngest in a cozy hug while the skyline glittered behind them. These are the kinds of unscripted, genuine moments that make family photography in Chicago so meaningful.

Best Photo Spots in the Park

• Skyline Overlook: Arguably the park’s best spot. This wide open view showcases Chicago’s architecture in all its glory.
• Tree-Lined Walkways: Great for walking shots, sibling portraits, or sweet parent-child moments.
• Circular Fountain Area: Adds a little structure and symmetry for more formal family photos.
• Grassy Knolls with Lake Views: Ideal for sitting shots, snuggles, and laid-back lifestyle portraits.

Tips for a Great Family Session at Olive Park

• Dress in soft, neutral tones to let the natural scenery and skyline pop.
• Arrive about 15 minutes early—the entrance is tucked away near Navy Pier and can take a minute to find.
• Bring snacks, wipes, and favorite toys for younger kids to help with breaks and bribery.
• Golden hour (1 hour before sunset) is the best time for dreamy lighting and fewer crowds.

Making Family Memories Last

At Albany Capture, we believe that family photos aren’t about perfect smiles or matching outfits. They’re about connection, emotion, and capturing your family exactly as you are—beautifully imperfect and full of love.

Whether your kids are toddlers or teens, we’ll help you feel at ease so we can capture images that truly reflect your bond. Milton Lee Olive Park gives us the space and the backdrop to do just that.