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Delight in these award-winning bungalow gardens

New and long-time bungalow owners showcased their best garden work

A bungalow with a brick exterior and bay window has an American flag near the door and an eclectic garden with a red-leaf tree, yellow and green shrubbery, and wildflowers.
Andrew & Lindsay McKone Front Garden Winners
Photos courtesy of the Chicago Bungalow Association

For the third year in a row, the Chicago Bungalow Association (CBA) has sought out the best gardens and awarded top prizes to homeowners with particularly green thumbs. There aren’t any landscape architects cultivating these flowery window boxes and verdant yards—that’s what makes the already perfect gardens so charming.

To enter the contest, homeowners must be a part of the bungalow association which also advises members on everything from how to research your home’s history to maintenance basics and historic design guidelines.

Nearly 4,000 people voted for gardens in three different categories: Front garden, rear or side garden, and window/planter boxes. The best in each group took home a $250 cash prize, received handmade planters by Craeft, a $50 gift certificate from City Grange, and get their hard work featured on CBA.

The winning landscapes are highly coveted, and even the runner-ups are spectacular too. There are tons of photos and mini videos showcasing garden details on CBA’s website but we’ll share a few of our favorites below.

Front yard

A side view of the front yard shows a garden planted close together with green leafy plants, pink and yellow flowers, white hydrangeas, and tall grasses.
A close-up view of the McKone’s front yard.

First prize in the category goes to Andrew and Lindsay McKone who ripped out three dense, overgrown pine trees to make space for a garden full of native plants and flowers. The first time homeowners in West Ridge, grew the front yard plant by plant for over a year as they picked up what was in bloom each season from nearby shops. Their garden features wildflowers, hydrangeas and a red-leaf Japanese maple tree.

Rear or side yard

A red-leafed Japanese maple tree stretches out to a wooden pergola. A white, bearded man sits reading a book with a glass of white wine. A back view of the white house with red awnings is visible through the garden path.
The pergola is one relaxing part of the new backyard.
A carpet lays underneath a cushioned bench seat with two other chairs creating a seating area underneath a candle chandelier in the middle of a green yard.

In Irving Park, Michelle Weiner tore down the garage to transform her backyard into a more inviting space. A winding gravel pathway separates plots of flowers and greenery but one of the best features of this yard is the ivy-covered brick wall that mimics Wrigley Field’s iconic outfield. Even down to the yellow numbers that mark the feet from home plate—except their number is 12,672.

Window and planter boxes

Colorful plants with pinks, magentas, reds, greens, and yellows make the front of this brick bungalow house lively.
Some planters and window boxes were found at estate sales.
A close-up view of a painted, wooden planter box with thin grasses, pink flowers, and lavender in the sun.

In Hermosa, which is known for its historic bungalow district, Venus and Juan Rodriguez won for their overflowing flower boxes and planters. Much of the work comes from Venus, she has a fondness for taking in plants that need a little TLC and searches estate sales for interesting planters. Juan submitted their house without telling his wife, so she was fully surprised when she won. And excited to put the money right back into gardening.