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Homestead on the Roof, Chicago, IL

Homestead on the Roof

4.5
4.5
749 Reviews
$50 and over
Portuguese
A photo of Homestead on the Roof restaurant

Homestead on the Roof

4.5
$50 and over
Portuguese
West Town

Make a booking

2 people
19:00
  • Neighbourhood 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

View details

Additional information

  • Dining style
    Casual Elegant
  • Price
    $50 and over
  • Cuisines
    Portuguese, Farm-to-table, Contemporary European
  • Hours of Operation
    Thu–Sat 17:00–23:00 Dinner Wed, Sun 17:00–21:00
  • 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
  • Area
    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
  • 4.4Value

NoiseModerate

Review summary

AI-generated from verified diner reviews
Homestead on the Roof is a charming rooftop retreat in West Town, celebrated for its "beautiful but unpretentious" atmosphere and "high quality, high value" touches. Diners rave about the "fabulous" food and "delicious" cocktails, making it an ideal spot for date nights. While service can be slow during busy times, the overall experience is positive, with many guests eager to return.

749 Reviews
  1. Jen

    Chicago

    2 reviews

    5.0

    2 reviews

    Dined on 25 September 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 20 September 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 16 September 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 15 September 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 14 September 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 2 September 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 25 August 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 24 August 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 23 August 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

    7 reviews

    5.0

    7 reviews

    Dined on 21 August 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.

A photo of Homestead on the Roof restaurant

Homestead on the Roof

4.5
$50 and over
Portuguese
West Town

Make a booking

2 people
19:00
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 />
  • Area
    West Town
  • Hours of Operation
    Thu–Sat 17:00–23:00 Dinner Wed, Sun 17:00–21:00
  • 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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