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 Chef Jesse Badger. 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


Jesse Badger

Jesse Badger

Chef de Cuisine

Jesse Badger has more than two decades of experience in every facet of the restaurant industry, including management positions in both the kitchen and dining room, as well as experience as a wholesale distributor. He is also a Certified Coffee Steward through Counter Culture Coffee’s national training program and a Certified Sommelier from the Court of Master Sommeliers.

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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