Homestead on the Roof

4.4
690 Reviews
$31 to $50
Contemporary Latin
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 Chef Ivan Valdez.

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.

Support Homestead on the Roof during COVID-19

Safety precautions

Cleaning & Sanitizing
  • Surfaces sanitized between seatings
  • Common areas deep cleaned daily
  • Digital, disposable or sanitized menu provided
  • Sanitizer or wipes provided for customers
Physical Distancing
  • Limited number of seated diners
  • Distancing maintained in common areas
  • Extra space between tables
Protective Equipment
  • Waitstaff wear masks
  • Diners must wear masks unless eating or drinking
Screening
  • Sick staff prohibited in the workplace
What 690 people are sayingWrite a review
Overall ratings and reviews
4.4based on all time ratings
4.4
food
4.3
service
4.6
ambience
4.0
value
Noise · Moderate
90% of people would recommend it to a friend
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vipOpenTable Diner
Chicago
1 review
Dined on January 8, 2021
Overall5food5service5ambience5

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

M
Msie
1 review
Dined on October 25, 2020
Overall4food5service5ambience5

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 Roof
Responded 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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N
Nicholas
1 review
Dined on October 16, 2020
Overall5food5service5ambience5

Great food, service, and ambiance. I can't wait to visit again.

Homestead on the Roof
Responded on October 20, 2020

Thank you Nicholas for taking the time to rate and review your experience with us! We are glad you enjoyed everything Homestead has to offer! Unfortunately we have shut down for the season, but we are opening running a fun holiday themed pop-up at our venue! You can visit our website or social medias for more information! Thank you again and we hope to see you soon!

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OT
OpenTable Diner
Atlanta
1 review
Dined on October 16, 2020
Overall5food5service5ambience5

I had an amazing birthday dinner at homestead! My server Gabe made my experience memorable.

Homestead on the Roof
Responded on October 20, 2020

Thank you so much for taking the time to rate and review your experience with us! We are so happy you chose to celebrate your birthday with us! We will pass along your compliments to Gabe and the rest of our staff! Thank you again and we hope to see you soon!

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OT
OpenTable Diner
Chicago
1 review
Dined on October 11, 2020
Overall4food4service5ambience4

A different evening...! ❣️

Homestead on the Roof
Responded on October 20, 2020

Thank you for taking the time to rate and review your experience with us! We are happy to hear you had a unique and wonderful time! We hope to see you again next season!

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OT
OpenTable Diner
Naples
1 review
Dined on October 10, 2020
Overall5food5service5ambience5

Great anniversary dinner. Cozy. Great food.

Homestead on the Roof
Responded on October 20, 2020

Thank you for taking the time to rate and review your experience with us! We are glad you enjoyed everything and we hope to see you again soon!

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ML
vipMLS1
Chicago
3 reviews
Dined on October 10, 2020
Overall5food4service5ambience5

Tacos were great. We tried brisket, chicken and pastor. All good - brisket and chicken were the best. We had both salads on the menu. They were okay, not great. We enjoyed the bread plate. We didn’t have cocktails as it was really a cold evening so we stuck with red wine which was good. Service was very friendly and efficient. It’s such a beautiful space and look forward to going back when it warms up again.

Homestead on the Roof
Responded on October 20, 2020

Thank you so much for taking the time to rate and review your experience with us! We are glad you enjoyed your experience even though it was a little chilly outside! Unfortunately we are now closed for the season, but we are running a fun holiday themed pop-up at our venue! Go to our website and social medias for more info! Hope to see you again soon!

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OT
vipOpenTable Diner
Chicago
1 review
Dined on October 9, 2020
Overall3food4service4ambience1

Poor seating arrangement

OT
OpenTable Diner
Des Moines
2 reviews
Dined on September 26, 2020
Overall5food5service5ambience5

Double date

Homestead on the Roof
Responded on October 2, 2020

Thanks for taking the time to rate your experience with us! We are glad you enjoyed all aspects of your experience on your double date! We are closing for the season soon, but our food menu is now available on Uber Eats so you can order our food right from home! Thank you again and we hope to serve you soon!

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OT
vipOpenTable Diner
Chicago
3 reviews
Dined on September 26, 2020
Overall5food4service5ambience5

Enjoyed a dinner on their beautiful rooftop last weekend. Tried several of the appetizers and they were all delicious. We enjoyed the uniqueness of the menu. Looking forward to their 21’ season.

Homestead on the Roof
Responded on September 30, 2020

Thank you for taking the time to rate and review your experience with us! We are so glad you enjoyed all aspects of your experience, especially the food! We are also looking forward to the 21' season, but we are open for two more weeks, so we hope to see you before then!

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OT
OpenTable Diner
1 review
Dined on September 25, 2020
Overall5food5service5ambience5

Our server Gabriel was outstanding. He gave awesome recommendations. The food was also fantastic!

Homestead on the Roof
Responded on September 30, 2020

Thank you for taking the time to rate and review your experience with us! We are so glad you enjoyed your experience! We will pass along your compliments to Gabriel and the rest of our staff! We hope to see you again before the season ends!

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OT
vipOpenTable Diner
Chicago
1 review
Dined on September 25, 2020
Overall5food5service5ambience5

Great atmosphere, amazing food, and friendly staff! Went on a Friday night with my friend, and was great for catching up!

Homestead on the Roof
Responded on September 30, 2020

Thank you for taking the time to rate and review your experience with us! We are glad you enjoyed your experience and we hope to see you again soon!

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JL
vipJLS84
Des Moines
8 reviews
Dined on September 25, 2020
Overall5food5service5ambience5

The food is outstanding! I had dinner here with a mix of out-of-towners and Chicago natives, and everyone was impressed. Our server Franklin was super friendly and helpful, we had indoor seating that had great ventilation (so everyone felt safe), COVID precautions and communication were strong, and the overall experience was excellent. Of a full weekend dining out in the city, this was by far my favorite and the favorite of the group.

Homestead on the Roof
Responded on September 30, 2020

Thank you so much for taking the time to rate and review your experience with us! We take our COVID restrictions and guidelines very seriously, so we are happy to hear you felt comfortable dining with us! We will pass along your compliments to Frankie and the rest of our staff! We hope to see you again soon before our season ends!

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TL
vipTimL
Chicago
38 reviews
Dined on September 25, 2020
Overall5food5service5ambience5

Had a wonderful experience. Great food , service and ambience. Will be back.

Homestead on the Roof
Responded on September 30, 2020

Thank you Tim for taking the time to rate and review your experience with us! We are glad you enjoyed your experience! We hope to see you before our season ends!

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S
Summerlovin
Chicago
2 reviews
Dined on September 24, 2020
Overall5food4service5ambience5

Homestead on the Roof is a great date night spot. They pay attention to detail with covid-19 safety. I hadn’t been back since the pandemic, but they were able to maintain the ambience with all the restrictions. The food is delicious and staff are friendly. Thanks for a great night.

Homestead on the Roof
Responded on September 30, 2020

Thank you for taking the time to rate and review your experience with us! We take our COVID restrictions and guidelines very seriously, so we are happy to hear you felt comfortable dining with us! We are glad you enjoyed all aspects of your experience! We hope to see you again soon before the season ends!

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AG
AllysonG
1 review
Dined on September 23, 2020
Overall5food5service5ambience5

Food was awesome, drinks were awesome, and our server was so sweet & lovely. We had an amazing time- the rooftop is beautiful!

Homestead on the Roof
Responded on October 2, 2020

Thank you Allyson for taking the time to rate and review your experience with us! We are glad you enjoyed all aspects of your experience! We are closing soon for the season but our food is now available on Uber Eats so you can have our food delivered to your door!

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H
Helen
Orlando
2 reviews
Dined on September 19, 2020
Overall5food5service5ambience5

Food is delicious. Ambiance is wonderful. Service is exceptional!

Homestead on the Roof
Responded on September 23, 2020

Thank you Helen for taking the time to rate and review your experience with us! We are glad you enjoyed everything! We hope to see you again soon before the season ends!

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OT
vipOpenTable Diner
Chicago
4 reviews
Dined on September 19, 2020
Overall5food5service5ambience5

Easily one of the best meals I’ve ever had. The restaurant itself is beautiful and the ambiance was wonderful (even on a somewhat chilly September evening). We got the bread platter and elotes, which blew our minds. The brioche was some of the flakiest and most flavorful breads I’ve ever tasted. Then we got the chicken thigh and al pastor tacos— both of which were cooked to perfection. The homemade corn taco kicked it to the extreme. Honestly wish I could relive this meal. Side note, the staff was wonderful and attentive and made the experience even better.

Homestead on the Roof
Responded on September 23, 2020

Thank you for taking the time to rate and review your experience with us! We are so happy you had such a wonderful experience! We take great pride in all of our food, drinks, and service so it's great to know you enjoyed everything! We hope to see you again before the season ends!

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KK
KimK
Chicago
3 reviews
Dined on September 19, 2020
Overall5food5service5ambience5

Excellent service, delicious food and cocktails. All waitstaff in masks and following precautions. So happy to have found this hidden gem! We will be back.

Homestead on the Roof
Responded on September 23, 2020

Thank you Kim for taking the time to rate and review your experience with us! We take our COVID restrictions and guidelines very seriously, so we are happy to know you felt safe dining with us! Also happy to hear you enjoyed all our menu has to offer! We hope to see you again soon before we close for the season!

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CS
CamilleS
Fayetteville
2 reviews
Dined on September 18, 2020
Overall5food5service5ambience5

Amazing food. The mussels, elote, and tacos (chicken and mushroom) are to die for. Going to be sad when it closes for the season!

Homestead on the Roof
Responded on September 23, 2020

Thank you Camille for taking the time to rate and review your experience with us! We are sad we will be closing for the season soon too, but glad you came and enjoyed everything we have to offer! Hopefully we see you one more time before the season is over!

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R
vipRaybanjay
Hawaii
18 reviews
Dined on September 12, 2020
Overall5food5service5ambience4

Gabriel was fantastic. He knew the menu, like the back of his hand. The food was excellent as well. We would love to check out the brunch very soon.

Homestead on the Roof
Responded on September 16, 2020

Thank you for taking the time to rate and review your experience with us! We will pass along your compliments to Gabriel! Homestead doesn't serve brunch at the moment, but West Town Bakery & Diner located right below us do! We hope to see you there soon!

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c
chichaz
Chicago
4 reviews
Dined on September 3, 2020
Overall5food5service5ambience5

The service at this spot is a real standout. I mean the ambiance and food are also amazing, but the service will really push you over the edge in a good way! So friendly, personable, attentive, knowledgeable, etc. Simply excellent!

Homestead on the Roof
Responded on September 9, 2020

Thank you for taking the time to rate and review your experience with us! We are happy to hear you enjoyed all aspects of your experience! We will pass along your compliments to the rest of our staff! We hope to see you again soon before the season ends!

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L
amyL
Chicago
3 reviews
Dined on September 3, 2020
Overall5food5service5ambience5

What a great experience, all around! Definitely recommend!

Homestead on the Roof
Responded on September 9, 2020

Thank you Amy for taking the tie to rate and review your experience with us! We are glad you enjoyed your time with us! We hope to see you again soon before the season ends!

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a
anns
1 review
Dined on August 30, 2020
Overall3food2service5ambience5

The rooftop itself is lovely. Service was fine. You can’t get the pizza on the rooftop. It’s Mexican Farr only.The food was half as good and 3 times the price of Antique Taco. We would only go back for drinks and the ambiance.

Homestead on the Roof
Responded on September 3, 2020

Thank you Ann for taking the time to rate and review your experience with us! We are part of the same company as Roots, but we are a separate restaurant so we do have a different menu! We are glad you were still able to enjoy our drinks and nice rooftop garden setting! We appreciate the honest feedback as it is one of the only ways we can continue to improve especially in these difficult times. Please reach out to General Manager, Lisa, at lmangiameli@thefifty50com with any other feedback.

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MS
MeganS
1 review
Dined on August 29, 2020
Overall5food5service5ambience5

I can’t rave enough! I was instantly pleased with the service and friendliness of staff -they created an amazing atmosphere. As if that wasn’t enough, the food and cocktails were incredible. I will definitely recommend this place to all of my fiends looking for a delicious (and Covid-conscious ) place to eat in Chicago.

Homestead on the Roof
Responded on September 3, 2020

Thank you Megan for taking the time to rate and review your experience with us! We are glad you enjoyed all aspects of your experience! We take our Covid restrictions very seriously so we are happy to hear you felt comfortable dining with us! We will pass along your compliments to the rest of our staff! We hope to see you again soon before the season ends!

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W
vipWinnie
Chicago
51 reviews
Dined on August 27, 2020
Overall5food5service5ambience5

My favourite for outdoor dining! The garden and trellises among ths tables provide a charming venue. Exceptional wait staff are knowledgeable and friendly making the dining a most pleasant experience. The food is delish and beautifully presented.

Homestead on the Roof
Responded on September 3, 2020

Thank you Winnie for taking the time to rate and review your experience with us! We are glad you enjoyed your experience in our beautiful garden! We will pass along your compliments to the rest of our staff! We hope to see you again soon!

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F
vipFamilybrown
Chicago
53 reviews
Dined on August 26, 2020
Overall5food5service5ambience4

What a fabulous spot for a date or dinner with friends

Homestead on the Roof
Responded on August 29, 2020

Thank you for taking the time to rate and review your experience with us! We are happy you enjoyed your experience on our rooftop patio! We hope to see you again soon!

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m
vipmkr68
Chicago
79 reviews
Dined on August 22, 2020
Overall4food4service5ambience5

Overall really good food and service. Rooftop is a great spot. Appetizers were really good. Tacos were just okay - we had the pork tacos which were good but could have used a bit more flavor. Chicken tacos were very bland.

Homestead on the Roof
Responded on August 29, 2020

Thank you for taking the time to rate and review your experience with us! We appreciate your feedback on your appetizers and tacos! Honest feedback is the only way we continue to improve especially in these difficult times. We'd love to hear more about your experience, please reach out to General Manager, Lisa Mangiameli, lmangiameli@thefifty50com. We look forward to hearing from you and hope to see you again soon!

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m
mary
Chicago
11 reviews
Dined on August 22, 2020
Overall3food5service5ambience2

we were sitted on a crickety old porch next to a RTU that was covered . When booking the reservation the other rooftop area was shown however there was no table available so we were seated on the other side of the roof. HOWEVER; the service and food was fabulous. I would definately recommend and go back but would specify I want to sit on the pretty rooftop venue

Homestead on the Roof
Responded on September 3, 2020

Thank you Mary for taking the time to rate and review your experience with us! Unfortunately due to Covid-19 we have a very limited number of tables we can put on that section of the rooftop. We are glad you enjoyed the rest of your experience even though you didn't get your preferred spot on the patio. We'd love to have you back this season and we'd make sure you could be on the upper deck patio. Please reach out General Manager, Lisa, at lmangiameli@thefifty50com. Hope to hear from you soon.

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TM
TrevorM
1 review
Dined on August 21, 2020
Overall3food5service5ambience2

After making reservation, which didn’t make a distinction between inside and outside; they said our reservations were for inside and would refuse to seat us at the open tables in the outdoor patio area. Hostess refused even after showing the open table reservation.

Homestead on the Roof
Responded on September 3, 2020

Thank you Trevor for taking the time to rate and review your experience with us! We understand that booking a spot on the rooftop on Opentable can be a little bit confusing and frustrating. We are sorry to hear you weren't able to get your ideal spot on the patio. We'd love to invite you back and make sure you can have a spot on the upper-deck rooftop. Please contact our General Manager, Lisa, at lmangiameli@thefifty50com. We hope to hear from you soon.

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RP
RaysheenP
1 review
Dined on August 21, 2020
Overall5food5service5ambience5

Ambience is beautiful at Homestead. The food is delicious and the service is top notch. Gabriel really knew his stuff and we enjoyed his recommendations. The mussels and chicken thigh tacos were amazing.

Homestead on the Roof
Responded on August 26, 2020

Thank you, Raysheen, for taking the time to rate and review your experience with us! We are glad you enjoyed all aspects of your experience! We will pass along your compliments to Gabriel as well! We hope to see you again soon before the season ends!

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GG
vipGinaG
Chicago
3 reviews
Dined on August 21, 2020
Overall5food5service5ambience5

Really beautiful dinner. We had a great time and the service was outstanding!

Homestead on the Roof
Responded on August 26, 2020

Thank you, Gina, for taking the time to rate and review your experience with us! We are glad you enjoyed your experience and we hope to see you again soon!

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B
Brett
Chicago
1 review
Dined on August 16, 2020
Overall5food5service5ambience5

Great ambiance. Great precaution with COVID. Food was incredible, only wish I was able to eat and try more! Will hopefully be back soon to enjoy before the season changes.

Homestead on the Roof
Responded on August 21, 2020

Thank you Brett for taking the time to rate and review your experience with us! We are glad you enjoyed all aspects of your experience! We take our Covid restrictions very seriously so we are glad you felt comfortable dining with us! We hope to see you again soon!

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E
vipElle
Chicago
20 reviews
Dined on August 15, 2020
Overall3food3service4ambience2

I was under the impression that the actual restaurant was located in a outdoor, rooftop garden. Instead, the restaurant has a few different dining areas- one being an outdoor, rooftop garden. So make sure you call first, to see where they have availability & where they plan on putting you. We were seated in a sort of “hallway.” The floor boards of the hallway were so bouncy, making it hard to sip drinks any time servers walked by. Kind of a bummer. Drinks & food were good- pretty small menu. Main course took a while to be served.

Homestead on the Roof
Responded on August 26, 2020

Elle, thank you for taking the time to rate and review your experience with us! Honest feedback is the only way we can continue to improve especially in these difficult times. Unfortunately due to Covid, we only seat about 14 tables on the upper patio, which is less than half of the capacity in other years. We'd love to talk more about this issue and how we do our best to deal with these situations. Please reach out to our GM, Lisa, at lmangiameli@thefifty50com. We hope to hear from you soon!

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s
vipsinglepayer
Chicago
1 review
Dined on August 15, 2020
Overall5food5service5ambience5

The food was delicious, the staff were pleasant and very accommodating.

Homestead on the Roof
Responded on August 21, 2020

Thank you for taking the time to rate and review your experience with us! We are glad you enjoyed your food and took notice of our attentive service staff! We hope to see you again soon!

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J
vipJohn
Chicago
5 reviews
Dined on August 14, 2020
Overall3food4service2ambience3

Servers were either short staffed or not paying much attention, but all in all food and drinks arrived fast and was tasty.

Homestead on the Roof
Responded on August 26, 2020

Thank you, John, for taking the time to rate and review your experience with us! We apologize that we missed the mark on some aspects of your experience! We take pride in our quick and attentive service and clearly we missed the mark during your time with us. We do appreciate the honest feedback as it is one of the only ways we can continue to improve during these times. Please reach out to GM, Lisa Mangiameli, at lmangiameli@thefifty50com. We look forward to hearing from you.

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e
echristmas
Chicago
52 reviews
Dined on August 14, 2020
Overall4food4service4ambience4

great atmosphere, really tasty well though out food, imaginative cocktails and the friendliest staff around. Homestead hit a home run with us. we'll be back soon. already sent a friend

Homestead on the Roof
Responded on August 26, 2020

Thank you for taking the time to rate and review your experience with us! We are glad to see you enjoyed the majority of your experience with us! We always encourage honest feedback as it is one of the only ways we can continue to improve, especially in these difficult times. Please reach out to General Manager, Lisa Mangiameli, at lmangiameli@thefifty50com if you have any feedback to share. We look forward to hearing from you and hope to see you again soon.

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SJ
SJLIII
San Francisco
3 reviews
Dined on August 12, 2020
Overall5food5service3ambience5

Food was absolutely delicious. A little on the pricier side for some of the items, but the flavor makes up for it. The ambiance is great, giving you the feel of an outdoor patio with the privacy of a rooftop, but only one story up. Almost feels like you are on a neighbor's deck. The servers were very friendly, but there was confusion about who our server actually was, when multiple showed up to take our orders various times. And you are also required to order all food at once, not being able to add items later, which is inconvenient. Not to mention that one of the deserts took over 30 minutes to come out, when the other ones came right away. Maybe there was some chaos given Covid, I'm not really sure. But the flavors put together by the chef made the minor difficulties worth it. Totally recommend it.

Homestead on the Roof
Responded on August 21, 2020

Thank you for taking the time to rate and review your experience with us! We are glad you enjoyed your dining experience even with the couple hick-ups experienced during service. We also appreciate the feedback you have given us, honest feedback is the only way we can continue to improve especially in these difficult time. We hope to see you again soon!

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OT
OpenTable Diner
Chicago
4 reviews
Dined on August 9, 2020
Overall5food5service5ambience5

I won another date. The food was awesome!!

Homestead on the Roof
Responded on August 15, 2020

Thank you for taking the time to rate and review your experience with us! We are glad you enjoyed your food and overall experience! We hope to see you again soon on your next date night!

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OT
OpenTable Diner
Chicago
1 review
Dined on August 9, 2020
Overall5food5service5ambience5

Excellent meal from start to finish! They ran out of the mussels app so we will need to come back to try it.

Homestead on the Roof
Responded on August 15, 2020

Thank you for taking the time to rate your experience with us! We are glad you enjoyed your experience and we hope to see you again soon to try our mussel dish!

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Homestead on the Roof is rated 4.4 stars by 690 OpenTable diners.

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