About Homestead on the Roof

Our story


Our Story

A West Town Hidden Gem

"There is no sincerer love than the love of food"

- George Bernard Shaw

Welcome. Homestead On The Roof— our cozy rooftop restaurant— is tucked away above Roots Handmade Pizza in the heart of West Town & features farm-fresh seasonal fare from Executive Chef Scott Shulman. The magic of Homestead is its 85-seat outdoor rooftop patio with full view of the L-shaped, 3,000 square foot organic rooftop garden, two massive, vertical hanging gardens, dozens of planter boxes full of fruits, veggies and herbs, and a fireplace. 

Homestead was named a “Top 100 Fit for Foodies Restaurants in America” by OpenTable, named one of the “10 Best New American Restaurants In Chicago” by OpenTable, and has been named one of the best rooftop/outdoor restaurants in Chicago by multiple media outlets.

Our approach


Every winter our team plans out a planting schedule for more than 7,000 square feet of lush, rooftop garden space. Our first planting begins in early April, typically with hearty greens and durable produce, and we plant 3 more times until early Autumn. We write our menus based around our planting schedule allowing the chef's complete freedom to let the season's bounty dictate the direction they take their food.  


Indoor & outdoor dining area

ENJOYABLE & comfortable

ENJOYABLE & comfortable


A Chicago Urban Oasis

With lush overflowing gardens, warm Edison string lights, a brick fireplace, and a warm summer breeze, it is no wonder Homestead on the Roof was named a top 100 restaurant for outside dining in the US by Open Table. Wood tables were crafted by Waldon Bros wood works and our chef team works daily to make sure we are harvesting fresh produce and herbs from the garden in order to serve you the highest quality possible. 

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Dusk Wedding
Interior Homestead


Warm & Comfortable

The interior of Homestead is open year round for private dinners and happy hour and it is the perfect spot to enjoy a candlelit dinner when the weather doesn't permit outdoor seating. With a fully stocked bar and easy access to the outdoor patio, the interior of Homestead is a versatile and warm space, perfect for cocktail hour.

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Our most valuable asset


Scott Shulman

Scott Shulman

Executive Chef

Believing that the restaurant business is “all about creating smiles,” Shulman realized his passion for cooking in college when his aunt was diagnosed with breast cancer. Accompanying her to doctor’s appointments and treatments, one afternoon the pair watched a Food Network program where a roasted chicken was prepared. Recalling how the sight of the chicken sparked a hunger in her she hadn’t experienced in weeks, Shulman immediately went to work recreating the recipe they saw on TV. She savored every bite of his creation, and he’s been cooking ever since.

Emily Phillips

Emily Phillips

Sous Chef

Christopher Teixeira

Christopher Teixeira

Pastry Chef / Partner

Christopher Teixeira is the executive pastry chef/partner for The Fifty/50 Restaurant Group and oversees all of the pastry, bread and dessert programs at West Town Bakery, Homestead On The Roof, Steadfast, and Portsmith.



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