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Homestead on the Roof, Chicago, IL

Homestead on the Roof

4.5
4.5
749 Reviews
$50 and over
Portuguese

Make a reservation

2 people
7:00 PM
  • Neighborhood gem
  • Great for outdoor dining
  • Charming
Homestead On The Roof— our cozy rooftop restaurant— is tucked away above Roots Handmade Pizza in the heart of West Town & features a farm-fresh Portuguese-influenced menu from Chef Christopher Teixeira.

The warm & cozy interior features a seasonally rotating tasting menu, 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 a 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.

Private dining

Private dining

Book your next event with us

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Additional information

  • Dining style
    Casual Elegant
  • Price
    $50 and over
  • Cuisines
    Portuguese, Farm-to-table, Contemporary European
  • Hours of operation
    Thu–Sat 5:00 pm–11:00 pm Dinner Wed, Sun 5:00 pm–9:00 pm
  • Phone number
    (773) 332-2354
  • Payment options
    AMEX, Discover, Mastercard, Visa
  • Dress code
    Smart Casual
  • Executive chef
    Chris Teixeira
  • Catering
    Homestead on the Roof does have the capabilities to cater outside events and venues. Please email events@homesteadparties.com
  • Private party facilities
    One of the city's best rooftops with a garden, cobblestone fireplace, rustic candlelit chandelier, & vine-climbing pergola, Homestead is a premier year round destination for your most special events and corporate buyouts.
  • Private party contact
    Jena Cherry: (773) 904-1149
  • Neighborhood
    West Town
  • Cross street
    Winchester (entrance through ROOTS HANDMADE PIZZA)<br />
  • Parking details
    Metered parking available all along Chicago Avenue & Winchester.
  • Public transit
    Damen Ave "50" CTA bus. Chicago Ave "66" CTA bus.
  • Entertainment
    None
  • Additional
    Banquet, Bar/Lounge, Beer, Cocktails, Full Bar, Non-Smoking, Patio/Outdoor Dining, Patio/Outdoor Dining, Wine

What 749 people are saying

Overall ratings and reviews

Reviews can only be made by diners who have eaten at this restaurant

4.5
4.5 based on recent ratings
  • 4.6Food
  • 4.1Service
  • 4.7Ambience
  • 4.3Value

NoiseModerate

Review summary

AI-generated from verified diner reviews
Homestead on the Roof offers a unique dining experience with a beautiful, unpretentious setting. The charming rooftop is a "wonderful hidden gem," perfect for a relaxed evening. Guests praise the "fantastic" food, creative cocktails, and friendly service. The spot is ideal for date nights or dinners with family.

749 Reviews
  1. Jen

    Chicago

    2 reviews

    5.0

    2 reviews

    Dined on September 25, 2024

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Outstanding all around, a Wonderful hidden gem! Love this place.

    Is this helpful?

  2. OpenTable Diner

    Detroit

    1 review

    5.0

    1 review

    Dined on September 20, 2024

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Awesome experience, friendly waiter Nigel was great. Food was stellar. Place was a little hard to find but overall excellent evening with them.

    Is this helpful?

  3. Amanda

    Chicago

    7 reviews

    5.0

    7 reviews

    Dined on September 16, 2024

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Food is wonderful (we shared the whole duck dinner) and the rooftop garden is such a beautiful place to eat on a perfect Chicago evening.

    Is this helpful?

  4. Matt

    Austin

    1 review

    5.0

    1 review

    Dined on September 15, 2024

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 4
    Awesome secret spot with fantastic Portuguese cuisine.

    Is this helpful?

  5. Michelle

    Minneapolis

    2 reviews

    1.0

    2 reviews

    Dined on September 14, 2024

    1. Overall 1
    2. Food 2
    3. Service 1
    4. Ambience 4
    We got seated 35 minutes after our reservation time, our server was barely attentive and had poor table side manner and food was pretty mediocre especially for the price. Overall, disappointed.

    Is this helpful?

  6. Nicholas

    San Francisco

    5 reviews

    vip
    4.0

    5 reviews

    Dined on September 2, 2024

    1. Overall 4
    2. Food 4
    3. Service 1
    4. Ambience 4
    Food was great. Service was very slow at a half full restaurant. Also the table that sat down after us was served before us.

    Is this helpful?

  7. Gloria

    Chicago

    10 reviews

    vip
    2.0

    10 reviews

    Dined on August 25, 2024

    1. Overall 2
    2. Food 3
    3. Service 1
    4. Ambience 3
    I would not suggest dining here. The roof top was ok but the service was very poor and food just ok. The server apologized that they were understaffed but that didn’t compensate for not getting our drinks timely, trying to understand the wine selection and food preparation. Sad to say take this one off your list

    Is this helpful?

  8. Eric

    Chicago

    1 review

    4.0

    1 review

    Dined on August 24, 2024

    1. Overall 4
    2. Food 4
    3. Service 4
    4. Ambience 5
    Duck fried rice a bit salty for my liking but otherwise great food and ambience

    Is this helpful?

  9. Chrisy

    Chicago

    5 reviews

    5.0

    5 reviews

    Dined on August 23, 2024

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Lovely experience all around! Excellent menu and presentation- enjoyed the octopus, scallops and short rib in particular, but everyone was exceptional. Cocktails, service and ambience perfect setting both for group or date night. Great music too- highly recommend

    Is this helpful?

  10. Jeffrey D

    Los Angeles

    5 reviews

    5.0

    5 reviews

    Dined on August 21, 2024

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Dinner was wonderful and the staff was really friendly!

    Is this helpful?

FAQs

Homestead on the Roof is rated 4.5 stars by 749 OpenTable diners.

Yes, you can generally book this restaurant by choosing the date, time and party size on OpenTable.

Make a reservation

2 people
7:00 PM
Google Map for Homestead on the Roof

1924 W Chicago Ave, Chicago, IL 60622

Additional information

  • Cross street
    Winchester (entrance through ROOTS HANDMADE PIZZA)<br />
  • Neighborhood
    West Town
  • Hours of operation
    Thu–Sat 5:00 pm–11:00 pm Dinner Wed, Sun 5:00 pm–9:00 pm
  • Price
    $50 and over
  • Cuisines
    Portuguese, Farm-to-table, Contemporary European
  • Dining style
    Casual Elegant
  • Dress code
    Smart Casual
  • Parking details
    Metered parking available all along Chicago Avenue & Winchester.
  • Public transit
    Damen Ave "50" CTA bus. Chicago Ave "66" CTA bus.
  • Payment options
    AMEX, Discover, Mastercard, Visa
  • Executive chef
    Chris Teixeira
  • Entertainment
    None
  • Additional
    Banquet, Bar/Lounge, Beer, Cocktails, Full Bar, Non-Smoking, Patio/Outdoor Dining, Patio/Outdoor Dining, Wine
  • Phone number
    (773) 332-2354
  • Catering
    Homestead on the Roof does have the capabilities to cater outside events and venues. Please email events&#64;homesteadparties.com
  • Private party facilities
    One of the city's best rooftops with a garden, cobblestone fireplace, rustic candlelit chandelier, & vine-climbing pergola, Homestead is a premier year round destination for your most special events and corporate buyouts.
  • Private party contact
    Jena Cherry: (773) 904-1149
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