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Homestead on the Roof

1924 W. Chicago Ave. (Wolcott Ave.) Send to Phone
Farm-to-table fare and craft cocktails rule at this rooftop spot in West Town.


Dinner nightly
Open late

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Homestead on the Roof, Chicago, IL

Operations may be disrupted due to COVID-19. Be sure to contact the restaurant to find out its current status and offerings.

Homestead on the Roof Restaurant Review

About the restaurant & décor: An urban oasis above Chicago Avenue, this 85-seat West Town restaurant is a local’s spring and summer destination. Enter through Roots Handmade Pizza, and head upstairs to a patio flanked by planter boxes, an outdoor fireplace and tables positioned under Edison-style bulbs. A metal chandelier hanging from a pergola lends drama to the space, but the overall vibe is cozy and relaxed.

Likes: Rooftop dining; neighborhood style.
Dislikes: It’s only open during spring and summer.

Food & Drinks: Diners reap the rewards of the rooftop garden thanks to chef Scott Shulman’s vibrant menu. A disc of buttery salmon semi crudo paired with a sesame cracker makes for a light, summery opener. Five-way beets get a kick of spiced pistachio and goat cheese, an easy segue to main events. A hunky piece of Alaskan halibut nestles on a smear of Parmesan gratiné and sun-dried tomato sauce and creamed kale. Creamy arancini makes the dish more decadent. A seared to pink on the inside New York strip is sized just right to enjoy its accompanying side: a petite bowl of fluffy, buttery mashed potatoes. If there’s room for dessert, savor the strawberry shortcake crème brûlée. A crisp Sancerre makes for easy sipping, one of many choices on the 100-bottle spirits list.

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