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Interior - Homestead on the Roof, Chicago, IL

Homestead on the Roof

4.7 (760)
$31 to $50
Portuguese
1924 W Chicago Ave, Chicago, IL 60622

Make a booking

A photo of Homestead on the Roof restaurant

Homestead on the Roof

4.7
$31 to $50
Portuguese
West Town

Make a booking

2 people
7:00 pm

About this restaurant

  • Neighbourhood gem
  • Innovative
  • Great for outdoor dining
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 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.

Dining areas

Additional information

  • Dining style
    Casual Elegant
  • Price
    $31 to $50
  • Cuisines
    Portuguese, Farm-to-table
  • Hours of Operation
    Dinner Thu–Sun 17:00–22:00
  • Contact
    733322354
  • Website
    https://www.homesteadontheroof.com/
  • 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
    Monique Davis: (312) 256-2546
  • Location
    1924 W Chicago Ave, Chicago, IL 60622
  • Area
    West Town
  • Cross street
    Winchester (entrance through ROOTS HANDMADE PIZZA)<br />
  • Parking Details
    Metered parking available all along Chicago Avenue &amp; Winchester.
  • Public transport
    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

Private dining

Concierge
AI Beta

Our AI assistant, Concierge, is here to answer your questions about this restaurant.

Menu

This menu from Homestead on the Roof.

View menu on restaurant's website

Videos

Shared by creators who recently dined at this restaurant.

  • Profile image

    sophinchicago

    Quaint rooftop in the city serving Portuguese inspired dishes! I loved the duck fried rice and the beautiful Friday evening vibes . . . #chicago #chicagofoodie #choosechicago #eaterchicago #explorechicago

Videos are powered by Seekeasy. How this content is generated

Reviews

OpenTable reviews from verified diners

Reviews from people who have dined at Homestead on the Roof.

4.7

4.7
(760)
  • 4.7Food
  • 4.5Service
  • 4.8Ambience
  • 4.6Value

Noise • Moderate

Loved For

  • Chicago / Illinois

    Innovative

  • Chicago

    Innovative

Review summary

AI-generated from verified diner reviews
Homestead on the Roof is a "hidden gem" with a spectacular rooftop oasis and delicious Portuguese-inspired cuisine. Reviewers rave about the "amazing food," with standout dishes like the duck fried rice and Portuguese spare ribs. Service is friendly, creating a fun atmosphere perfect for groups. Highly recommended for a seasonal dining experience.
760 Reviews

  1. Jason Gold

    Chicago / Illinois14 reviews

    5.0

    Dined on 26 September 2026

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Great food, drinks, service, enviornment, and all of the above. This is a must stop if you are in the city during rooftop season.

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  2. Meghan Gold

    Detroit / Eastern Michigan6 reviews

    5.0

    Dined on 11 September 2026

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Food was excellent, service was even better. Above and beyond what I expected all around. It’s a shame it isn’t open year round, it’s incredible!

    Is this helpful?

  3. KJ

    Chicago / Illinois1 review

    5.0

    Dined on 10 September 2026

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    The inside of the restaurant is charming, but the showstopper is the rooftop patio. It is an oasis surrounded by lush foliage. The food is delicious and presented beautifully. The Portuguese spare rib appetizer is a very generous portion and tasty. The duck fried rice is a must-have side. The crispy pork belly was our favorite entree. We accompanied our meal with wine from the Douro valley (Portuguese) and finished with chocolate flan and passion fruit rice pudding. Service was attentive and friendly. Highly recommend!

    Is this helpful?

  4. Stephen Gold

    Chicago / Illinois79 reviews

    4.0

    Dined on 7 September 2026

    1. Overall 4
    2. Food 5
    3. Service 3
    4. Ambience 5
    All around good experience in this Portuguese type restaurant. Chicken skins being my personal favorite, but there was nothing bad with what we ordered. Service was not great, and no elevator. Expect a massive stair climb.

    Is this helpful?

  5. Jennifer Gold

    Chicago / Illinois3 reviews

    5.0

    Dined on 4 September 2026

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Delicious food, wonderful atmosphere and fantastic service. We really enjoyed our dinner here last night!

    Is this helpful?

  6. Rachel

    Chicago / Illinois1 review

    5.0

    Dined on 29 August 2026

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Great evening on the roof with my girlfriends. We celebrated my friends birthday. Vibe was great. GET THE SHORT RIBS 🤤

    Is this helpful?

  7. Andrew

    Mexico City1 review

    5.0

    Dined on 27 August 2026

    1. Overall 5
    2. Food 5
    3. Service 3
    4. Ambience 5
    Service took a long time but it was nice and relaxed, and the atmosphere was so nice it was worth it to spend a little extra time over dinner. We did ask for the check along with our aperitifs to save a little time on getting out of there… but it’s truly a wonderful hidden gem of a place in Chicago

    Is this helpful?

  8. Hope Gold

    Chicago / Illinois13 reviews

    5.0

    Dined on 21 August 2026

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    This is really a gem of a place. First, you have to walk through the West Town Bakery to enter the restaurant. The place coats you in donut smell. Plus it's just an interesting operation to see! Once you reach the roof, the beautiful garden awaits. The staff is really kind and helpful. The wine list is great. The food blew us away. We almost ate the entire menu. It's such great value. We were so full and happy. Finally, since it's outside, the noise level is minimal.

    Is this helpful?

  9. Lolu Gold

    Chicago / Illinois7 reviews

    5.0

    Dined on 15 August 2026

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Amazing food with great service… shout out to Makayla. Definitely; will be back.

    Is this helpful?

  10. Mary Gold

    Chicago / Illinois12 reviews

    5.0

    Dined on 14 August 2026

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    The food was outstanding. The sangria was delicious and not too sweet. The rooftop ambiance is so cool and intimate and the service was top notch. It is a fun place to go with a group who likes to try different foods! I can’t wait to go back!

    Is this helpful?

Dining areas

Additional information

  • Dining style
    Casual Elegant
  • Price
    $31 to $50
  • Cuisines
    Portuguese, Farm-to-table
  • Hours of Operation
    Dinner Thu–Sun 17:00–22:00
  • Contact
    733322354
  • Website
    https://www.homesteadontheroof.com/
  • 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&#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
    Monique Davis: (312) 256-2546
  • Location
    1924 W Chicago Ave, Chicago, IL 60622
  • Area
    West Town
  • Cross street
    Winchester (entrance through ROOTS HANDMADE PIZZA)<br />
  • Parking Details
    Metered parking available all along Chicago Avenue &amp; Winchester.
  • Public transport
    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

Featured in

  1. Home
  2. United States
  3. Chicago / Illinois
  4. Chicago
  5. West Town

Make a booking

A photo of Homestead on the Roof restaurant

Homestead on the Roof

4.7
$31 to $50
Portuguese
West Town

Make a booking

2 people
7:00 pm
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