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, and a decorative outdoor fireplace.
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.
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.
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
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 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 Filipino/American 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.
This season's cocktail menu, was created by The Fifty/50 Group's Beverage Director, Julieta Campos.
After jumpstarting her career at Grant Achatz’s The Aviary, she spent the next several years honing her skills behind the bar at The Berkshire Room until she took over the beverage program at The Whistler. In 2018, Campos was recognized in NewsFeed’s 40 Under 40 list as a rising star in the industry. That same year, she also received a Jean Banchet Award nomination for Best Mixologist.
“At the core of my work, I am motivated by delivering bold and unique concoctions and building a community. As the new director of beverage and bar operations at The Fifty/50 Restaurant Group, I aim to consistently keep these values in mind, thinking outside the box when it comes to menu development while also fostering a welcoming environment for everyone on the team."