Our Story

Welcome. Homestead On The Roof— our cozy, secret rooftop— is tucked away above Roots Handmade Pizza in the heart of West Town. The magic of Homestead is its 85-seat outdoor rooftop patio with full view of the L-shaped, 1,000 square foot rooftop garden overflowing with beautiful flowers, two massive vertical hanging gardens, a decorative outdoor fireplace, and a brand new water feature. 

Homestead was named a “Top 100 Fit for Foodies Restaurants in America” and one of the “10 Best New American Restaurants In Chicago” by OpenTable, and has been named among the best rooftop/outdoor restaurants in Chicago by multiple media outlets. Join us every summer for an exclusive new pop-up menu, available for a limited time. Our venue is a true Chicago hidden gem that will charm guests and leave a lasting impression.

Literal Farm-To-Table


This season’s pop-up menu is inspired by Chef Bryan Collante’s Filipino heritage, life travels, and dishes that have influenced him in his career. The food is bold, humble, and memorable with an emphasis on sour, sweet, salty, and funky flavors that will spark a cherished memory for each guest.

Standout dishes include the Whole Black Bass and Bone-In Ribeye, which according to Chef Bryan, is the hardest and most rewarding menu item to cook. "There's something about taking such a great piece of meat and transforming it."

Globally influenced. Asian inspired. Locally Grown.



  • Seating for up to 100

  • Decorative Brick fireplace

  • Suitable for large groups and weddings

  • An incredible summer happy hour

With lush overflowing gardens, warm edison string lights, a decorative 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, and among the best rooftops in the city by multiple local media outlets. Nestled between two natural brick buildings, our venue is a true Chicago hidden gem that will charm your guests and leave a lasting impression.


  • 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.


Bryan Collante


Bryan Collante is the chef at Homestead On The Roof, as well as its lower-level sister restaurant West Town Bakery & Diner.


Born in the West Coast and raised in the Midwest, Bryan is a first-generation Filipino American. He credits his older brother, public access TV and being home alone for inspiring him to become a chef. Bryan originally attended school to become a fine artist...That is until he sat in on a cooking class and the rest is history. 


This season’s menu is inspired by Chef Bryan’s memories, life travels, and dishes that have influenced him in his career. He hopes guests walk away from their meal with a reminder of a cherished memory that will keep them coming back for more.


Frankie Duchimaza

Lead Bartender

Our cocktail menu, was created by longstanding The Fifty/50 Group employee, Frankie Duchimaza. He created handmade cocktails infused with housemade syrups to go along with Chef Bryan's cuisine.