Our Story

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. The magic of Homestead is its 85-seat outdoor rooftop patio with full view of the L-shaped, 1,000 square foot organic rooftop garden, two massive, vertical hanging gardens, dozens of planter boxes full of Summer produce 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.

Literal Farm-To-Table

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.  

This season, our culinary team has curated a special menu inspired by their cultural roots with a focus on home-cooked meals made from scratch.


Some of the recipes come right from their family's kitchen, such as Chef Ivan's Mole Negro, which is inspired by his mother and her home state of Michoacan, Mexico. Additionally, Chef's tacos are piled atop handmade tortillas, made to order. The tortilla press he uses has been passed down his family for generations.

Chef Chris Teixeira draws inspiration from Latin American culture and his own Portuguese roots for this season's dessert menu, including Creme Catalana, paired with Horchata Ice Cream.

Comfort Food From Home


  • Seating for up to 100

  • Brick fireplace

  • Suitable for large groups and weddings

  • An incredible summer happy hour

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. 


  • Seats 80 comfortably

  • Full Bar

  • Perfect for daytime brunches and private dinner parties

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.

Chris 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.​

The son of Portuguese immigrants, Teixeira’s first memories of baking were of his mother, who worked in the same bakery for 25 years and sparked his interest in pastry creation. Named one of five "Under-the-radar pastry chefs whose names you ought to know" by Chicago Tribune’s Phil Vettel in 2013 and included on Zagat’s “30 under 30” list in 2014

A James Beard Award semifinalist in the “Rising Star Chef of the Year” category for his work at Homestead on The Roof in 2015, Teixeira believes in keeping it simple and local, letting nature tell him what ingredient is best. 

Ivan Valdez

Chef De Cuisine

Ivan Valdez is the chef de cuisine at Homestead as well as it’s lower-level sister restaurant West Town Bakery & Diner

Valdez was born and raised in the Logan Square neighborhood and graduated from Kendall College with a culinary arts degree. Prior to enrolling at Kendall College, Valdez spent six years in the United States Marine Corps Reserve and finished his military career as a Corporal.


Valdez is channeling his Mexican-American heritage to make Homestead’s menu this season an extension of his “home” – drawing inspiration from his mother’s recipes and his father’s hometown of Mexico City.

Homestead on The Roof

1924 W Chicago Ave

(above Roots Pizza)

Phone: (773) 332-2354