Homestead on the Roof

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607 Reviews
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$31 to $50
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Contemporary American

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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 from Executive Chef Jesse Badger.

The warm & cozy interior features a seasonally rotating tasting menus, which incorporates ingredients from our own farm and local vendors into our nationally recognized cuisine.

The magic of Homestead is its 85-seat outdoor rooftop patio with full view of the L-shaped, 3,000 square foot organic rooftop garden, two massive, vertical hanging gardens, dozens of planter boxes full of fruits, veggies and herbs, and a fireplace.
Dining Style
Casual Elegant
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Contemporary American, Tapas / Small Plates, Farm-to-table
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Hours of operation
Tue–Sat 5:00 pm–10:00 pm
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Phone number
(773) 332-2354
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Payment options
AMEX, Diners Club, Discover, MasterCard, Visa
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Dress code
Smart Casual
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Executive chef
Jesse Badger
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Homestead on the Roof does have the capabilities to cater outside events and venues. Please email Morgen McGarrie for more information
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Cross street
Winchester (entrance is through ROOTS HANDMADE PIZZA)
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Parking details
Metered parking available all along Chicago Avenue & Winchester.
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Public transit
Damen Ave "50" CTA bus. Chicago Ave "66" CTA bus.
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Special events & promotions
For special events, please email Jacklyn Seavern,
Homestead is available for private dining and buyouts.
Our culinary team will work with you to craft menus to fit your specifications.
We do have catering menus for all types of price points and options that include chef stations, plated dinners, and open bar.
Please email Jacklyn for a copy of our menu and we will set a time to discuss a custom menu with our Chef Team.

Homestead on the Roof also caters for larger outside venues at The Bridgeport Art Center, Baderbrau, The Rookery and Studio Manarchy.

Additional information can be found on our website,
Banquet, Bar/Lounge, Beer, Cocktails, Full Bar, Non-Smoking, Outdoor dining, Private Room, View, Wine