Homestead on the Roof

4.5
583 reviews
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$31 to $50
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Contemporary American
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 Executive Chef Jesse Badger.

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.
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What Insiders Are Saying

The Infatuation
7.7

So many farm-to-table restaurants, zero farms around. Homestead changes that a bit by growing vegetation on site.

Ratings 7.5-8.0:These are restaurants that are reliable, tasty, and particularly good for whatever we have deemed them “Perfect For.” Hit up a 7.7 for Date Night with confidence, as long as you don’t need the restaurant to be the most interesting thing that happens that night.
What 583 People Are Saying
Overall ratings and reviews
Reviews can only be made by diners who have eaten at this restaurant
4.5based on recent ratings
4.4
food
4.3
service
4.6
ambience
4.1
value
Noise · Quiet
90% of people would recommend it to a friend
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OT
Calgary
1 review
Dined 2 days ago
Overall 5food 4service 4ambience 5

Such cool atmosphere, amazing food & service! Would recommend!

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OT
Chicago
2 reviews
Dined 4 days ago
Overall 5food 5service 5ambience 5

Excellent! Great atmosphere, food was outstanding, great date spot but several other groups dining around us, waiter was the best! Sat outside, but has a decent space inside as well (get outside!).

The only weird thing is walking through Roots Pizza and up a back stairwell until you find this place... there's a sign hanging at front of Roots Pizza entrance, and had to go in and ask where to go

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LM
Baton Rouge
1 review
Dined on July 13, 2019
Overall 4food 4service 4ambience 5

I had the special filet. It was the toughest filet I’ve ever had. And, the most expensive!!

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OT
Chicago
1 review
Dined on July 13, 2019
Overall 5food 5service 5ambience 5

Everything was wonderful from the service to the food to the ambiance. We enjoyed the entire experience. Our food had layers of flavors that were unique and delicious.

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CN
Chicago
4 reviews
Dined on July 12, 2019
Overall 4food 5service 3ambience 5

The atmosphere was fantastic and area is beautifully decorated. The food tasted delicious, highly recommend the raclette for an app! However the entree portions definitely didn't match... my fried chicken had 5 large pieces while my boyfriend's steak frites had a tiny portion of meat. Service was good but the waiter seemed timid and then sort of disappeared when it was time to bring the check.

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OT
Chicago
8 reviews
Dined on July 10, 2019
Overall 4food 4service 4ambience 4

Perfect local rooftop

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N
Chicago
15 reviews
Dined on July 6, 2019
Overall 3food 2service 3ambience 2

The past two years my husband and I had enjoyable anniversary dinners at Homestead on the Roof. This year we included another couple, promising a wonderful experience. Of course no one can control the wind. It was too gusty for our comfort so we requested to be seated inside. I had made the reservations 3 1/2 weeks prior. I wasn’t told of the West side fest. The band and crowd noise would’ve been even more annoying if we had sat outside.
The menu was not as good this time around. The chef did accommodate my dietary restrictions, but truly, the menu lacks for not having a couple of vegan options (no gluten would be a big help as well as I am also gf/df, not by choice). My husband and the other couple are adventurous foodies, and they too were disappointed in the offerings. Our server was good, friendly. However at the end of the meal, check and payment became a slow process. I’d like to try again but only if the menu had some other offerings that made it much easier for a person like myself to find something. The chef did make a concerted effort this time around. He made something from veggie ingredients available, which was creative.

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OT
1 review
Dined on July 3, 2019
Overall 5food 4service 4ambience 5

Great place for food and drinks
Rooftop patio makes the summer nights enjoyable

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T
Chicago
1 review
Dined on June 29, 2019
Overall 5food 5service 5ambience 5

Incredible. Beautiful spot. Amazing food and drinks. Superb service. LOVED IT!!!

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SK
1 review
Dined on June 27, 2019
Overall 5food 5service 5ambience 5

Perfect for a first date or casual dinner with beautiful ambience and scenes. Servers were super cool, friendly, and hospitable! I’ll be back!

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R
Grand Rapids
1 review
Dined on June 27, 2019
Overall 5food 5service 5ambience 5

Awesome staff! It started storming after we already arrived. Ahead of time, they asked if they could move us underneath the awning. During the storm they were very attentive, kept great attitudes and were very accommodating. Awesome place, we plan on going back when the weather is nicer!!

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g
Chicago
3 reviews
Dined on June 22, 2019
Overall 5food 5service 4ambience 5

Interesting, great tasting food and drink selections; well presented; and a good value for the quality! Our server was a bit intense (fast, a bit frantic talking) in his initial introduction (and we noticed this with his other tables as well), but overall likable. There wasn't much interaction after the food was brought to the table. My wife and I would've appreciated a brief "re-introduction" of the items we ordered when they were delivered (esp. since most dishes have at least 1 or 2 interesting/lesser known ingredients), but it didn't hamper our experience much. The ambiance is fantastic. It's peaceful and the tables are spaced appropriately for not being a part of others' conversations. My wife, being vegetarian, was able to find plenty of items from which to pick, though a lot of the veggie items this time around were mushroom focused. Overall, a great experience for our first time and we'll definitely be back.

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l
Chicago
12 reviews
Dined on June 22, 2019
Overall 5food 5service 5ambience 4

The benches they have are not very comfortable and maybe could be updated or at least padded ?

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LH
Atlanta
1 review
Dined on June 21, 2019
Overall 5food 5service 5ambience 5

This place is very serious about the food and service they provide to customers, and it's clear it is their passion. They take farm to table to new heights (pun intended). I had a dinner here to celebrate my graduation from business school, and the food and drinks were delicious. Highly recommended!

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OT
Chicago
1 review
Dined on June 21, 2019
Overall 5food 5service 5ambience 5

Food was excellent. Service was fantastic. Drinks were very good.

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r
Chicago
8 reviews
Dined on June 21, 2019
Overall 4food 4service 4ambience 4

Homestead is one of my favorite restaurants in the city. I've never had anything but a pleasant experience there, although I have to admit this past visit was a bit underwhelming. Service was ok, despite having to wait an hour for our first plate to arrive... Also had requested to sit outside, although was told it wasn't open when we arrived. An hour later the host was seating people outside... I'll chalk this up too an anomaly instead of the norm and hope to return soon.

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OT
Detroit
2 reviews
Dined on June 21, 2019
Overall 3food 2service 4ambience 3

The Raclette was a good appetizer. The ramen was not a good main dish. The fried pork cube tasted like it was fried in month old grease. Wouldn't recommend!

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OT
Chicago
1 review
Dined on June 18, 2019
Overall 3food 3service 2ambience 4

Paloma was lackluster and the appetizer elements were off (artichoke fritter sauce way too salty, as was one of the bread basket accoutrement and the cauliflower was very vinegary). However, the fried chicken was delicious, and my dining partner liked his burger. Entrees seem to be the strong suit

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t
Chicago
15 reviews
Dined on June 18, 2019
Overall 2food 3service 2ambience 5

We waited 30 mins for our drinks. Lovely atmosphere. They also ran out of duck.

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HS
1 review
Dined on June 14, 2019
Overall 5food 5service 5ambience 5

We love Homestead! It's beautiful sitting outside by the rooftop gardens. The food and drinks are wonderful and tasty and interesting combinations. ALWAYS get the bread basket :)

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D
Chicago
24 reviews
Dined on June 8, 2019
Overall 4food 4service 3ambience 4

Cheers put with picked, potatoes, bread to dip shockingly good... Bar service very slow

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PD
Chicago
1 review
Dined on June 8, 2019
Overall 5food 5service 5ambience 5

The rooftop was a beautiful location for a perfect Spring night dinner. We tried several small plates and all of them were excellent. The drinks were creative and delicious and the service was impeccable. Looking forward to going back later in the season when their garden is being utilized.

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s
Chicago
4 reviews
Dined on May 31, 2019
Overall 3food 1service 4ambience 4

Great location, cutest rooftop ever. The service was good. The food was NOT. the lamb mousse and the steak were awful. Could barely chew the steak, I don’t understand how you can ruin steak. The mussels were not very fresh. The duck was ok. The racklette and the chicken were the only things we liked. The drinks were fine. We racked up 350 ish dollars of a bill for low quality food.

If you go, get drinks and the chicken. I took my whole family and was a bit embarrassed by how bad the food was.

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c
Chicago
5 reviews
Dined on May 25, 2019
Overall 3food 3service 3ambience 5

I’ve been to this restaurant 3 time over the past 2 years and was very excited to take OOT family. What a disappointment. It was all table and no farm. Where were all the fresh vegetables and herbs? Why all the heavy sauces and dressings? And why try so hard on all your cocktails? Fresh is always best. Sadly not coming back.

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AS
1 review
Dined on May 23, 2019
Overall 5food 5service 5ambience 5

I will definitely be back. The food and drinks were great-the mussels in particular were memorable-and the service and ambiance were top notch.

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R
New York Area
27 reviews
Dined on May 18, 2019
Overall 5food 5service 5ambience 5

Loved everything. The only issue was the acoustics are awful. VERY loud, people have to yell to be heard. Would be great to find a way to adjust this...even just a little bit!

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TS
Chicago
4 reviews
Dined on May 18, 2019
Overall 5food 5service 5ambience 5

I love this place! Everything about it is fantastic. The food , service, ambiance, couldn't have been any better. Sarah our server was great and very helpful with recommendations. The bread basket is a must have. Living in the western suburbs we had about a 30 mile drive to get there but it was well worth the drive. We will definitely do it again!!

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A
1 review
Dined on May 18, 2019
Overall 3food 4service 4ambience 2

We requested outdoor rooftop as we were celebrating a special occasion. We were seated indoors where it was very bright and loud. We couldn’t hear each other or the waiter. Completely different vibe than the quiet rooftop that we wanted for my father’s 60th birthday. I felt embarrassed that my family came from out of town and I took them to a restaurant that felt like a noisy high school cafeteria. The outdoor area was about half full of other patrons. I don’t understand why they couldn’t honor our request for outdoor seating. Disappointing in that it created a completely different experience.

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JE
Chicago
3 reviews
Dined on May 17, 2019
Overall 4food 5service 4ambience 5

I had a great time whole here. The service could have been a little bit better but the food was delish. I highly recommend this place for anyone.

Just needs to work on the service. Tonight my server seemed stressed, cause of the sweat coming off his face, but the restaurant was not busy.

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n
Thailand
4 reviews
Dined on May 12, 2019
Overall 1food 1service 3ambience 3

I went here a few years ago when it first opened and it was great. I decided to return for Mother’s Day which happened to be a brunch. The selection and food were both terrible. It reminded me of a continental breakfast at a cheap hotel. It’s no wonder there were only four tables dining. This place sadly has gone downhill. I definitely won’t be returning and advise others to look elsewhere.

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EL
Washington DC
1 review
Dined on May 12, 2019
Overall 5food 5service 5ambience 5

Service and food were outstanding. Love the ambiance.

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PH
Chicago
4 reviews
Dined on May 12, 2019
Overall 5food 5service 5ambience 5

Sunday Mother’s Day Brunch was incredible. I would highly recommended for their special brunch dates.

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AG
1 review
Dined on May 3, 2019
Overall 5food 4service 5ambience 5

The food was really good! Highly recommend the Raclette and Fried Chicken. Service was helpful and quick. With the weather was better to eat outside, but the space is beautiful!

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LS
Chicago
3 reviews
Dined on April 21, 2019
Overall 5food 4service 5ambience 5

My wife & I went for Easter brunch and really enjoyed ourselves. The space is amazing on a secluded, yet open rooftop that gave us plenty of sunlight in the early afternoon. The buffet was very good, but is probably not representative of the normal fare served on a daily basis. The staff was very friendly and attentive. We had a great time and can't wait to go back once it opens up for dinner in a couple of weeks.

Homestead on the Roof
Responded on April 26, 2019

Lee, Thank you so much for the kind words! It could not have been a more beautiful day on the roof. And you are correct, our buffets are more traditional whereas our Homestead menu is inventive and seasonally inspired. We open for our regular season Saturday, May 4 and hope you will stop by to see what our chefs have created! Please feel free to introduce yourself to either myself or my assistant manager, Aldo. I look forward to your next visit! Best, Liz, GM

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TL
Chicago
1 review
Dined on April 21, 2019
Overall 5food 5service 5ambience 5

Went for the Easter Sunday Brunch and it was great. Cant speak for the normal menu but if its anything like the brunch it is going to be good.

Homestead on the Roof
Responded on April 26, 2019

Tim, Thank you for joining us on Easter! The buffet had quite the spread :) We open for our regular reason on Saturday, May 4th, so please come and see us again soon. We have an exciting and delicious menu planned! Best, Liz, GM

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AP
1 review
Dined on April 21, 2019
Overall 3food 3service 3ambience 3

Went to the Easter brunch. Not bad, not great. We got four drinks (two each) which basically doubled the price. For the amount of money spent, the overall value just didn't measure up. I have spent the same amount of money for some of the best meals/experiences I have ever had. Willing to give the restaurant another shot, but will not go to another brunch buffet. The staff didn't seem prepared when the first opened.

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OT
Chicago
5 reviews
Dined on February 7, 2019
Overall 5food 4service 5ambience 5

It was a wonderful evening- the food was lovely and I enjoyed the personalized service!

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JE
1 review
Dined on February 2, 2019
Overall 5food 5service 5ambience 5

It was only open because of Restaurant week. Usually closed in the wintertime but open when the weather gets better. Heard they have a really nice garden worth checking out.

I recommend the place. Chill atmosphere, serveice was great, and food was good. A little confusing to get there since it's a "restaurant in a restaurant" but I would suggest it to others overall

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C
Chicago
24 reviews
Dined on January 31, 2019
Overall 5food 4service 5ambience 5

This was a great Restaurant Week choice - normally Homestead on the Roof is closed all winter, so it was very special to be able to try it in January. Food was great and service was amazing. The manager himself waited on us for most of the night and was very attentive!

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OT
Chicago
2 reviews
Dined on September 29, 2018
Overall 5food 5service 5ambience 5

Amazing service!! Treated us so well on our anniversary

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