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Homestead on the Roof, Chicago, IL

Homestead on the Roof

4.4
4.4
718 Reviews
$50 and over
Portuguese
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.

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Private dining

Private dining

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Additional information

  • Dining style
    Casual Elegant
  • Price
    $50 and over
  • Cuisines
    Portuguese, Farm-to-table, Contemporary Latin
  • Hours of operation
    Dinner Wed, Thu, Sun 5:00 pm–11:00 pm Fri, Sat 5:00 pm–12:00 am
  • 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 is through ROOTS HANDMADE PIZZA)
  • 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 718 people are saying

Overall ratings and reviews

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

4.4
4.4 based on all time ratings
  • 4.4Food
  • 4.3Service
  • 4.6Ambience
  • 3Value

NoiseModerate

718 Reviews
  1. MelissaL

    Chicago

    1 review

    5.0

    1 review

    Dined on October 14, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    We did the black lagoon pop up which was pretty fun! Drinks were good and the food was really really good.

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  2. EmilieS

    Chicago

    2 reviews

    1.0

    2 reviews

    Dined on October 6, 2023

    1. Overall 1
    2. Food 1
    3. Service 1
    4. Ambience 1
    Open table let us make a reservation and the place closed before that. So came there and it was closed and we were allowed to stand around in the dark waiting. So not great

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  3. VictoriaG

    Memphis/West TN

    5 reviews

    vip
    2.0

    5 reviews

    Dined on October 4, 2023

    1. Overall 2
    2. Food 2
    3. Service 4
    4. Ambience 3
    We didn’t know it was a popup. The service was good, but the drinks and food were terrible. I think it is just the popup menu, as we have heard so many good things about this restaurant! We are hoping to try it again after the popup is over

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  4. Milo

    Chicago

    8 reviews

    5.0

    8 reviews

    Dined on September 30, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Service incredible, staff great, chef came out to talk about the food, best experience ever

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  5. DanG

    Chicago

    5 reviews

    5.0

    5 reviews

    Dined on September 17, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    My favorite restaurant in Chicago. Amazing seasonal venue at a beautiful rooftop. Always take my family and friends here when they visit. Staff are friendly and food is delicious. Couldn’t speak any higher of Homestead.
    Homestead on the RoofResponded on September 21, 2023
    Thanks, Dan for the wonderful review! I'm so glad you enjoyed your last visit with us! Hope to see you back soon :) -Chelsea, Homestead MGMT

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  6. JoshuaC

    Chicago

    1 review

    5.0

    1 review

    Dined on September 16, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Great qyiet rooftop spot in their garden with an ever changing seasonal menu
    Homestead on the RoofResponded on September 21, 2023
    Thank you so much for the awesome review! We hope to see you again before we close our doors for the season, cheers! -Chelsea, Homestead MGMT

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  7. GoodEats

    Chicago

    333 reviews

    vip
    5.0

    333 reviews

    Dined on September 7, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Homestead on the Roof is a true gem of a restaurant. The rooftop itself is lovely, and when combined with delicious food (particularly loved the salt cod croquettes and the charred octopus) and professional and friendly service (Robert was outstanding on our visit), this is a must-visit spot. We will be back again soon.
    Homestead on the RoofResponded on September 11, 2023
    Thank you so much for the awesome review! I am also always raving about the croquettes and octopus... so good! I'll pass along to praise to Robert and let him know he's doing something right :) Come back before the 29th! We close for the season that day and would love to host you and your friends again! -Chelsea, Homestead MGMT

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  8. AllMussel

    Richmond

    2 reviews

    3.0

    2 reviews

    Dined on September 4, 2023

    1. Overall 3
    2. Food 4
    3. Service 2
    4. Ambience 3
    Staff was into each other but not us. Asked twice for water, took about 30 minutes. We were instructed to order all courses at once. Dishes came out at glacial speed. Food was not competently prepared; almost broke our teeth on uncooked chickpeas in the salad. A disappointment given the reviews.
    Homestead on the RoofResponded on September 11, 2023
    I'm sorry to hear your last visit wasn't all that you'd hoped for. I do want to mention that you visited on a day where we were understaffed and overbooked (day before Labor Day). While we try our best to hit that mark for every single guest, unfortunately we are all human and mistakes do happen. I'm so sorry you were that table. I also want to mention that the Chickpea Salad intentionally has a mix of soft and crunchy chickpeas. This is intended to add textural interest, however I have no way of knowing whether your dish was prepared correctly or not. In the future, please make sure to bring any issues to management during your visit. That's what we are here for, and if a guest is having a problem with anything we want to know about it so we can correct it on the spot. I hope you'll try us again before the end of the season to give us another shot. -Chelsea, Homestead MGMT

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  9. RichardC

    Chicago

    1 review

    5.0

    1 review

    Dined on August 28, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Nice atmosphere, glad they had the fire pit outside. That made the restaurant feel cozy.

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  10. KarenB

    Chicago

    1 review

    5.0

    1 review

    Dined on August 14, 2023

    1. Overall 5
    2. Food 4
    3. Service 4
    4. Ambience 5
    wait staff helpful, wine list good, food very interesting -- good overall experience
    Homestead on the RoofResponded on August 16, 2023
    I'm glad you enjoyed what we have to offer here! We hope to see y'all again soon! -Chelsea, Homestead MGMT

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  11. OpenTable Diner

    Chicago

    1 review

    4.0

    1 review

    Dined on August 10, 2023

    1. Overall 4
    2. Food 4
    3. Service 5
    4. Ambience 5
    The gardens are lovely and the service is excellent. Loved the food. My friends thought it needed more flavor, but I loved the flavors. Ordered salt cod fritters, broccolini, octopus, and chicken. Tasty!
    Homestead on the RoofResponded on August 11, 2023
    Yay, I'm happy you had a good time during your last visit! It's also wonderful to hear that the service was on point. Hope to see y'all again soon! Next time y'all come in try the duck rice, it's one of the menu items that has a stronger flavor and it is SUPERB. Chelsea, Homestead MGMT

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  12. TerriS

    Chicago

    48 reviews

    5.0

    48 reviews

    Dined on August 10, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    This is an unusual restaurant, one must walk through the pizza place downstairs in order to get to Homestead. The roof deck is different, but comfortable and out of the sun. The food was excellent, we ordered tuna, cod and octopus and the spicy potatoes. Service was also great, Red was professional, friendly and gave us accurate descriptions of the food and it was fun to chat with him.
    Homestead on the RoofResponded on August 10, 2023
    Aw, I'm so glad y'all had a great visit! We are a bit unusual but that's what makes us a "hidden gem"! I passed your note along to Red and they were also very glad you all had a great time :) Hope to see y'all soon! -Chelsea, Homestead MGMT

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  13. OpenTable Diner

    Chicago

    3 reviews

    5.0

    3 reviews

    Dined on August 5, 2023

    1. Overall 5
    2. Food 5
    3. Service 4
    4. Ambience 5
    Delicious food and beautiful rooftop with flowers and other greenery. Each dish was outstanding.
    Homestead on the RoofResponded on August 6, 2023
    Yay, I'm so glad you like the food and ambiance here! So many folks have told me the garden looks great this year which makes me very proud. Of course the star of the show is our amazing cuisine, however :) My favorite is the Piri Piri Pork Belly and Baked Eggs! -Chelsea, Homestead MGMT

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  14. OpenTable Diner

    Charlotte

    2 reviews

    5.0

    2 reviews

    Dined on August 4, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Our server Hector was amazing! Food and drinks were beautiful. A great addition to our trip!!
    Homestead on the RoofResponded on August 6, 2023
    I'm so glad you enjoyed your visit with us! We are very proud that we were able to enrich your trip even further by providing great service, food, and ambiance. I'll let Hector know he's doing something right. It's a shining example of what we are trying so hard to provide here every day. Hope to see y'all in our neck of the woods again soon! -Chelsea, Homestead MGMT

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  15. Nickname

    Minneapolis

    1 review

    2.0

    1 review

    Dined on August 3, 2023

    1. Overall 2
    2. Food 4
    3. Service 1
    4. Ambience 3
    Service was atrocious and food portions were small, we waited an astronomical amount of time for drinks and our apps came out before the drinks, even though we ordered the food about 30 minutes after the drinks and the place wasn’t busy at all, maybe 3-4 other tables besides us. We had to get a manager to send our server to us twice and when he did show up he wouldn’t speak at a volume anyone could hear him. Just terrible all around.
    Homestead on the RoofResponded on August 10, 2023
    I'm so sorry about the quality of your service during your last visit. On a slow Wednesday like the day your party dined there should have been no issues whatsoever. I sent you a private message to ask for more details. Thank you for the feedback. -Chelsea, Homestead MGMT

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  16. DAVIDP

    Chicago

    3 reviews

    vip
    4.0

    3 reviews

    Dined on July 31, 2023

    1. Overall 4
    2. Food 5
    3. Service 5
    4. Ambience 5
    The food here is always excellent. Previous visit early this season found disappointing service but on this visit the service was good. Happy to report they refound their mojo.
    Homestead on the RoofResponded on August 2, 2023
    Thanks for the great review and for coming back to give us another chance! We always seem to have some embarrassing hiccups at the beginning of the season and I too am glad that we refound our mojo! Hope to see you again soon! -Chelsea, Homestead MGMT

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  17. AndyC

    Chicago

    8 reviews

    vip
    3.0

    8 reviews

    Dined on July 30, 2023

    1. Overall 3
    2. Food 3
    3. Service 2
    4. Ambience 3
    I've eaten at Homestead half a dozen times and have had some excellent meals, but this time was pretty disappointing.
    Homestead on the RoofResponded on August 2, 2023
    We're sorry to hear that you weren't satisfied with your last visit. I'm curious to know where we missed the mark. Was service slow that day? Were there other factors that contributed to service only hitting 2 stars?

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  18. OpenTable Diner

    Chicago

    1 review

    5.0

    1 review

    Dined on July 29, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    The food and ambiance was perfect. I especially loved the duck rice dish!
    Homestead on the RoofResponded on August 3, 2023
    The duck rice is awesome. Thanks for the review! -Chelsea, Homestead MGMT

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  19. louiseb

    New York City

    1 review

    2.0

    1 review

    Dined on July 27, 2023

    1. Overall 2
    2. Food 2
    3. Service 4
    4. Ambience 3
    3 plates came with baby greens (croquettes, octopus, chicken). Croquettes were soft (not crispy), chicken sauce was tasteless, and we couldn’t taste the saffron nor coconut sauce on the broccolini.
    Homestead on the RoofResponded on July 28, 2023
    Sorry to hear the food on your last visit wasn't to your taste! Your feedback will be cascaded to our team. The saffron cream is intentionally delicate and the coconut is the crunch sprinkled on top for clarification. -Chelsea, Homestead MGMT

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  20. SchroederComm

    Tallahassee

    10 reviews

    vip
    1.0

    10 reviews

    Dined on July 15, 2023

    1. Overall 1
    2. Food 2
    3. Service 1
    4. Ambience 2
    Wanted this to be as described on their website, but unfortunately it wasn’t what they advertise. Service was bad, food orders went unfulfilled, not worth it in a city with so many good restaurants. #dontbelievethehype

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  21. Becca

    Chicago

    24 reviews

    vip
    3.0

    24 reviews

    Dined on July 13, 2023

    1. Overall 3
    2. Food 3
    3. Service 3
    4. Ambience 4
    Ambience is beautiful here. Note that you will head straight back inside of Roots pizza to get to staircase for Homestead. Interesting menu. Some great items and some are fine. Portions can be inconsistent. Drinks were tasty though. Would come back for just drinks on a date.
    Homestead on the RoofResponded on July 19, 2023
    So glad that you enjoyed the drinks, we hope to see you again soon! -Chelsea, Homestead MGMT

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  22. SteveM

    Philadelphia

    5 reviews

    vip
    5.0

    5 reviews

    Dined on July 7, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Really great spot. Hidden gem. Fantastic atmosphere, food, everything. Highly recommend
    Homestead on the RoofResponded on July 8, 2023
    Thank you SO much for the great review! We're so happy you had a great time, and look forward to seeing y'all again soon :) -Chelsea, Homestead MGMT

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  23. jknott

    Chicago

    83 reviews

    vip
    5.0

    83 reviews

    Dined on June 25, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Incredibly delicious food. We loved EVERYTHING we ate. Our server, Connor, was excellent. My cocktail didn’t taste the way I thought it should. He went back and fixed it and didn’t leave our table until I was satisfied. I was satisfied. He informed us of the dishes and what to expect. The pork belly, scallops, smelt (never had them, but delicious), peri peri chicken, steak were all excellent. We will definitely be back, especially for the flan.

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  24. SydneyS

    Chicago

    8 reviews

    vip
    4.0

    8 reviews

    Dined on June 24, 2023

    1. Overall 4
    2. Food 5
    3. Service 3
    4. Ambience 5
    Homestead of the Roof is a beautiful space! We sat outside on the roof deck. We had read some reviews previously and were concerned about the service. We were sat and were not greeted for quite some time. Only then did the host that sat us ask us if we had been greeted yet, and after saying no, she offered to take our drink order. Our server came over after several more minutes and greeted us and we put in an order of bread, but still didn't have our drinks. We received the bread and after 30 minutes from being sat, finally had our drinks. Once we put our food in, things were fine, but it was really unfortunate that we were not helped for a significant amount of time and had to begin our meal without drinks. I would return for the food, the menu was delicious and we loved the octopus and the pork belly, and especially the rice pudding for dessert. The Portuguese rolls were delicious as well. Our waiter was great otherwise after the beginning.

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  25. OpenTable Diner

    Chicago

    5 reviews

    vip
    1.0

    5 reviews

    Dined on June 18, 2023

    1. Overall 1
    2. Food 3
    3. Service 1
    4. Ambience 4
    This restaurant was a most disappointing experience, considering we never ate our main courses. We never received our main courses after almost 2 hours of sitting at the table. Apparently, there was a waiter issue and they had to “refire” the main courses and we waited, waited, and waited until there was no more waiting. I asked to cancel the dishes missing and asked for the whole meal to be reimbursed, which they willingly did. Disappointing cause the food had promise. I will never go back again. The atmosphere was very pleasant.
    Homestead on the RoofResponded on June 22, 2023
    I remember your table being the most unfortunate circumstance that day. On top of an inattentive and unfocused server, your food ticket was somehow lost. Usually neither of these things happen, and especially don't happen to the same table! The fact that it did is completely unacceptable and not the standard we are aiming for. If you did decide give us another shot, we would definitely be sure to exceed those expectations. We appreciate the honest feedback. -Chelsea Scallion, Homestead MGMT

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  26. OpenTable Diner

    Philadelphia

    1 review

    vip
    3.0

    1 review

    Dined on June 17, 2023

    1. Overall 3
    2. Food 4
    3. Service 1
    4. Ambience 5
    Ooo food was good but the service was meh but ambiance incredible

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  27. RachelK

    Western NC

    3 reviews

    5.0

    3 reviews

    Dined on June 10, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    I learned about Homestead last year, and was excited to try their new menu. I was attached to last year’s, but this year is truly just as good. The food was authentic and clearly prepared with love, the staff was friendly and attentive, and the ambiance can’t be beat. I hope to be back many times this season!
    Homestead on the RoofResponded on June 15, 2023
    Yay, we are so happy we were able to wow y'all with the new menu! We can't wait to host y'all again! If you aren't a loyalty member already you should definitely become one and take advantage of all the perks involved, which include being able to use it at all of our sister-establishments (such as West Town Bakery and Roots downstairs, and Okay Dispensary next door ;) -Chelsea Scallion, Homestead MGMT

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  28. Wally

    Chicago

    4 reviews

    3.0

    4 reviews

    Dined on June 9, 2023

    1. Overall 3
    2. Food 3
    3. Service 3
    4. Ambience 5
    Main attraction was the ambiance, being outdoor on a rooftop. The food was just okay, nothing special, perhaps just not to our liking. Portions are small compared to the cost. The server could have been more knowledgeable on the menu and recommendations.
    Homestead on the RoofResponded on June 15, 2023
    Thank you Wally for that helpful review. Our goal is for our servers to be able to use their inside knowledge to guide guests through the menu, and if that's not happening we are missing the mark. We will be going over menu knowledge periodically with staff to ensure the best experience for our guests. I'm sorry to hear the food wasn't to your liking either! We hope to see y'all again to retry that and hopefully change your mind. -Chelsea Scallion, Homestead MGMT

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  29. OpenTable Diner

    Chicago

    1 review

    5.0

    1 review

    Dined on June 9, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    This place is such a hidden gem. The ambiance is incredible alone, but on top of that every single dish we had was delicious. The Portuguese rolls with port butter are to die for. Service was outstanding, would highly recommend homestead on the roof!
    Homestead on the RoofResponded on June 15, 2023
    Thank you so much for your review! We're so glad you enjoyed your experience with us and hope to see you again soon! If you haven't tried the flan yet I highly recommend it :) -Chelsea Scallion, Homestead MGMT

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  30. DeniseP

    Chicago

    2 reviews

    5.0

    2 reviews

    Dined on June 5, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Truly a hidden gem in wicker park!! Everything was amazing especially the duck fried rice, scallops and flan!
    Homestead on the RoofResponded on June 22, 2023
    I'm so happy you enjoyed your time here! We can't wait to have y'all back and do it all over again :) Cheers! -Chelsea Scallion, Homestead MGMT

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  31. DAVIDP

    Chicago

    3 reviews

    vip
    2.0

    3 reviews

    Dined on June 1, 2023

    1. Overall 2
    2. Food 5
    3. Service 1
    4. Ambience 4
    Food was superb. Service was slow and inattentive. Itemized bill was lower than credit card charges. 3% credit card charge was disclosed but amount did not appear on the itemized bill. We have been coming here for the 3 or 4 years. Food is great, The service has declined each year: the first year it was very good now it is unacceptable. We have noticed the same thing at the the sister restaurant, Roots, on Wells Street location. 50/50 group needs to get their act together. Nuisance charges are infuriating. If a place's prices are too low raise them. Don't sandbag customers!
    Homestead on the RoofResponded on June 3, 2023
    Hi David, I appreciate you taking the time to write out a helpful review. Slow and inattentive service is not what we are going for! I will make sure to go over this issue with my staff. As far as the 3% surcharge fee goes the cost of doing business has risen significantly, forcing us to try new things to mitigate those costs. If there is an issue at the time you can ask for a manager and we are more than happy to work with you or remove it. -Chelsea Scallion, Homestead Management

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  32. KatieH

    Chicago

    2 reviews

    2.0

    2 reviews

    Dined on May 31, 2023

    1. Overall 2
    2. Food 2
    3. Service 2
    4. Ambience 4
    We loved the ambience; however, we very underwhelmed with the food - the duck rice was an exception. The staff was very polite, but they could really improve on knowing the menu - food & drink - as well as clearing the table of finished dishes. We were even more underwhelmed at the end to learn that there is a 3% credit card fee added to your tab. Oofta!
    Homestead on the RoofResponded on June 3, 2023
    Hi Katie, I appreciate you leaving a review. I'm happy to hear you liked the duck rice and am sorry to hear that the rest of our menu didn't wow you. We will make sure to keep our education efforts going for our staff so they can better guide our guests. As always, if there is an issue with any fees on your bill please make sure to ask for a manager so I can work with you at the time. We can do things servers can't and I want you to leave happy! -Chelsea Scallion, Homestead Management

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  33. MarianaR

    Chicago

    2 reviews

    5.0

    2 reviews

    Dined on May 29, 2023

    1. Overall 5
    2. Food 5
    3. Service 4
    4. Ambience 5
    It was a great experience, with amazing food and vibe! I highly recommend going to Homestead on the roof!
    Homestead on the RoofResponded on June 3, 2023
    Thank you Mariana for the review! I'm glad you had a good time and hope to see you all again soon! -Chelsea Scallion, Homestead Management

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  34. DanG

    Chicago

    5 reviews

    5.0

    5 reviews

    Dined on May 28, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Our most favorite restaurant in Chicago. We’ve eaten at Homestead many times and their latest 2023 summer Portuguese menu is one of the best. Not only is the food fantastic but the space is a hidden gem and the staff could not be friendlier or more welcoming. Would 100% recommend to anyone.
    Homestead on the RoofResponded on May 28, 2023
    Thank you so much Dan! I'm happy to hear you had a great time and enjoyed our seasonal menu! The menu this year is amazing, all thanks to our talented Chef Chris Teixeira. He did a wonderful job curating a fresh interesting menu perfect for the space and we could not be more excited for the rest of the summer. Hope to see you again soon! -Chelsea Scallion, Homestead Management

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  35. Cms33

    Chicago

    14 reviews

    4.0

    14 reviews

    Dined on May 27, 2023

    1. Overall 4
    2. Food 4
    3. Service 4
    4. Ambience 5
    Great food in a nice setting, would definitely come here again
    Homestead on the RoofResponded on May 28, 2023
    Thank you for the review! We hope you come and see us again. Definitely try some more menu items. I believe they are all tasty in different ways :) -Chelsea Scallion, Homestead Management

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  36. rachelk

    Chicago

    9 reviews

    vip
    3.0

    9 reviews

    Dined on May 26, 2023

    1. Overall 3
    2. Food 3
    3. Service 5
    4. Ambience 4
    Cocktails and service were great. Food was extremely spicy and unbearable however staff were very accommodating.
    Homestead on the RoofResponded on May 28, 2023
    Thank you Rachel for the honest feedback! I'm happy to hear you loved our drinks and service. I believe that you may have had a better experience with food if we made sure the staff knows to check with guests when they order the spicier options. We have some milder seasoned food on the menu that I bet you would have liked a lot better if you had been steered in the right direction. Regardless, we will use this information to help guide better service in the future! -Chelsea, Homestead Management

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  37. LaurenB

    Milwaukee

    1 review

    5.0

    1 review

    Dined on May 24, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Delicious food, great drinks, in a beautiful setting. What more could you want?!
    Homestead on the RoofResponded on May 28, 2023
    Thank you Lauren for the fantastic review! I may be biased but I completely agree with you :) -Chelsea Scallion, Homestead Management

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  38. IsabellaR

    Chicago

    1 review

    5.0

    1 review

    Dined on May 24, 2023

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Fantastic! Excellent food, service and ambiance. Excited to return.
    Homestead on the RoofResponded on May 28, 2023
    Hi Isabella! So happy you enjoyed what we have to offer! We look forward to seeing you again :) -Chelsea Scallion, Homestead Management

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  39. OpenTable Diner

    Chicago

    1 review

    vip
    5.0

    1 review

    Dined on January 9, 2021

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    We arrived at the restaurant and was advised that they have been closed for the season for several weeks and would not be re-opening until spring

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  40. Msie

    Chicago

    1 review

    4.0

    1 review

    Dined on October 25, 2020

    1. Overall 4
    2. Food 5
    3. Service 5
    4. Ambience 5
    Homestead was great. There was a mishap between OpenTable and Homestead and somehow our reservation got lost. It was very disappointing because we made the reservation 2 months in advance and confirmed it the day before. We would have GREATLY preferred to sit outside but because the reservation was lost we had to sit inside which was frustrating. Luckily Homestead worked with us and found us a table despite the miscommunication between OpenTable and Homestead. Margaret
    Homestead on the RoofResponded on November 10, 2020
    Thank you for taking the time to rate and review your experience with us! We are so sorry about the weird mishap with your reservation, but glad that you were able to be accommodated regardless. Next season, when you make a reservation send me an email at jcameron@thefifty50com and I'll make sure to get you a great spot on the patio! Thanks again and hope to see you again soon!

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Safety precautions

  • Cleaning & sanitizing

    • Surfaces sanitized between seatings
    • Common areas deep-cleaned daily
  • Physical distancing

    • Limited number of seated diners
    • Distancing maintained in common areas
    • Extra space between tables
  • Screening

    • Sick staff prohibited in the workplace
    • Staff is vaccinated

FAQs

Homestead on the Roof is rated 4.4 stars by 718 OpenTable diners.

Not bookable

This restaurant is temporarily offline. Please contact the restaurant directly or check back shortly for availability.

Google Map for Homestead on the Roof

1924 W Chicago Ave, Chicago, IL 60622

Additional information

  • Cross street
    Winchester (entrance is through ROOTS HANDMADE PIZZA)
  • Neighborhood
    West Town
  • Hours of operation
    Dinner Wed, Thu, Sun 5:00 pm–11:00 pm Fri, Sat 5:00 pm–12:00 am
  • Price
    $50 and over
  • Cuisines
    Portuguese, Farm-to-table, Contemporary Latin
  • 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@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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