Homestead on the Roof

Rooftop Charm Meets Farm-to-Table Flavor in West Town

Homestead on the Roof is a cozy, rustic-chic restaurant tucked above Roots Handmade Pizza in Chicago’s vibrant West Town neighborhood. Specializing in seasonal, farm-to-table Portuguese-inspired cuisine, this rooftop gem offers a unique garden setting—complete with 85 seats surrounded by a 1,000-square-foot organic rooftop garden. The vibe is laid-back yet elevated, with twinkling string lights, fresh herbs growing nearby, and a menu that celebrates bold, earthy flavors.

Why Concert-goers love it

Just a short ride from many of Chicago’s top music venues, Homestead on the Roof is a great pick for a relaxing yet memorable meal before the show. The rooftop setting provides a peaceful escape from the city buzz, while the attentive service ensures you’re in and out on time. The menu rotates with the seasons, so you’ll always find something fresh and satisfying—ideal for fueling up before a night of dancing or singing along.

Who this Restaurant is great for

• Groups of friends looking to share small plates before the show
• Solo travelers who want a serene spot to dine with a view
• Couples enjoying a romantic weekend with concert tickets
• Fans who appreciate a more relaxed, scenic pre-show experience
• Budget-conscious music lovers seeking quality over flash

What People Say

Reviewers consistently praise the beautiful rooftop ambiance, calling it “a hidden oasis in the city.” The innovative seasonal menu wins big points for its freshness and creativity, with diners loving the house-made pastas, wood-fired breads, and creative takes on Portuguese fare. Service is described as friendly and well-paced, perfect for pre-concert timing. Many guests say it’s a “must-visit” for anyone wanting something off the beaten path.

Areas for Improvement

While the rooftop setting is a major draw, some guests note that weather can be a factor, especially on windy or rainy evenings. Seating is limited, so reservations are strongly recommended. A few diners mention that the menu, while delicious, may not be ideal for picky eaters or those expecting more traditional Portuguese dishes.

The Bottom Line

If you're seeking a cozy, garden-style rooftop experience with fresh, flavorful food before your concert, Homestead on the Roof hits all the right notes.