Homestead on the Roof

4.5
550 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 550 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
4.3
food
4.6
service
4.5
ambience
4.0
value
Noise · Quiet
83% of people would recommend it to a friend
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LS
Chicago
3 reviews
Dined 3 days ago
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.

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TL
Chicago
1 review
Dined 3 days ago
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.

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AP
1 review
Dined 3 days ago
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
23 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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E
Chicago
17 reviews
Dined on September 29, 2018
Overall 5food 5service 5ambience 5

It was a treat to dine on the rooftop before it closed for the season. Our server was fantastic and made great suggestions. Amazing meal and great beverages too!

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SS
1 review
Dined on September 27, 2018
Overall 5food 5service 5ambience 5

Homestead was wonderful! The food was very very good and so carefully and artfully prepared. The staff was incredibly kind, helpful and attentive and made great recommendations. The rooftop is quaint, quiet, and beautiful, a great ambiance for a relaxing and quiet dinner outside.
All around wonderful visit and will definitely be going back. Excited to see their menu next season!

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LK
Seattle
3 reviews
Dined on September 22, 2018
Overall 5food 5service 5ambience 5

Excellent evening celebrating our 6 year wedding anniversary! Service was great and the food was excellent. Perfect for a date night. They even offered complimentary champagne when we told our server we were celebrating. Highly recommend!

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JG
1 review
Dined on September 21, 2018
Overall 1food 2service 1ambience 2

Dinner meal was rushed as if the servers were ready to go home (if that is the case don't accept 9:45 reservations) , main entree was served even when not completing the appetizers, the fish entrees was undercooked even when sent back to the kitchen twice. Manager appologized for the bad experience. Offered to comp the main entrees which we never ate anyways and had to question them on the bill because I was still being charged for items that were supposedly being removed. Too many fantastic restaurants in Chicago definitely not worth going to this one.

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A
Chicago
14 reviews
Dined on September 21, 2018
Overall 3food 3service 3ambience 4

The menu highlights more of a safe, mild palate. I could possibly see my grandparents enjoying the meal, but for me there was nothing that wowed me. The service was a bit on the slow side for a Friday evening. They seemed to be understaffed. Many of our food items did not come out very hot. The ambience outside was quite beautiful, but that would be the only reason I would recommend Homestead.

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JD
Chicago
1 review
Dined on September 21, 2018
Overall 4food 5service 4ambience 5

We didn’t have a server for several minutes but when I flagged someone down, he took us over immediately and was terrific. That is my only complaint. Otherwise it’s truly a special place with excellent food and otherwise terrific service!

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ML
Atlanta
1 review
Dined on September 20, 2018
Overall 5food 5service 5ambience 5

Very romantic setting, candles, rooftop, not loud. We ate next to the rooftop garden. It is $$ but SO GOOD. The bread basket is amazing - came with honey butter, dipping oil, and southern chow chow. I believe the menu changes seasonally? We had pork chop which came with a delicious savory pie - very generous portion of pork - and the scallops with peas and bacon. Everything was perfectly cooked. Cocktails were great as well - had the cucumber/vodka/mint one, very refreshing! Will go back

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OT
Chicago
1 review
Dined on September 20, 2018
Overall 5food 5service 5ambience 5

It was amazing!! Food delicious & great drinks. One cold side & they took it off the bill! Knowledgeable staff- Great experience!

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TS
Chicago
4 reviews
Dined on September 15, 2018
Overall 5food 5service 5ambience 5

This was our first time at there. Everything from the food, ambiance and service was exceptional. The breadbasket is a great appetizer. Our waiter Aldo was fantastic. We will definitely come back.

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DJ
Los Angeles
2 reviews
Dined on September 7, 2018
Overall 5food 5service 5ambience 5

This is a beautiful romantic rooftop spot with fresh and delicious local farm-to-table fare. The trout was amazing.

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HH
Chicago
1 review
Dined on September 7, 2018
Overall 4food 5service 3ambience 5

Good food, cute rooftop, slow service even though it wasnt a busy night.

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LS
1 review
Dined on September 2, 2018
Overall 5food 5service 5ambience 5

We were celebrating our anniversary and Teddy's attention to detail made sure to make our evening special! The atmosphere was relaxing and pleasant. We both enjoyed our meals, the filet mignon was so tender and the pork chop was hearty and the pie was savory.

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CB
Chicago
1 review
Dined on August 25, 2018
Overall 5food 4service 5ambience 5

Anniversary

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KH
Chicago
1 review
Dined on August 25, 2018
Overall 5food 5service 5ambience 5

Simply lovely place to dine on a summer evening-food, service and ambiance were all perfect.

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OT
Chicago
1 review
Dined on August 25, 2018
Overall 5food 5service 5ambience 5

Great experience, always fun in the summer.

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PP
Chicago
7 reviews
Dined on August 24, 2018
Overall 5food 5service 5ambience 5

The trout was spectacular, so much flavor! They try to incorporate one ingredient from the garden in each dish, the trout had cherry tomatoes that were delicious. Each dish, even the vegetables have a unique concept such as pad Thai Brussels sprouts. Highly recommend Homestead on the Roof!

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V
Chicago
18 reviews
Dined on August 24, 2018
Overall 5food 5service 5ambience 5

Nice quiet meal. Excellent food and service. We were able to dine outside. It was quiet enough to have an enjoyable conversation. The waiter was knowledgeable and pleasant.

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z
Tampa
14 reviews
Dined on August 24, 2018
Overall 3food 5service 2ambience 2

Great food, but after that it fell off the table. Service was spotty at best. Then it got worse, we had only started eating our first course, when the entree's showed up. Really!

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J
Chicago
14 reviews
Dined on August 19, 2018
Overall 5food 5service 5ambience 5

We had a perfect night out on the roof. It is an urban gem. You have to luck out on weather which we did. Interesting, fresh menu with limited selections (which I like). Very seasonal and delicious. We had a great night and it was super relaxing with great service.

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MM
Baltimore
9 reviews
Dined on August 18, 2018
Overall 5food 4service 5ambience 5

Beautiful location outside on the roof! Loved the atmosphere, the noise level, and the delicious food. We were visiting from out of town and were happy to find something unique and delicious.

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f
Chicago
18 reviews
Dined on August 16, 2018
Overall 5food 5service 5ambience 5

Love the trout and scallops. We also tried the bread basket. My friend said "if you have to pay for bread, bread should be awesome" and it was. Will definitely come back and might come in the winter where you can sit in the area that is covered.

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KB
Chicago
3 reviews
Dined on August 15, 2018
Overall 4food 3service 3ambience 5

Waiter was intrusive. Food was good but not as amazing as I’d expected. Ambiance is beautiful. Concept also is awesome. Definitely worth a second try.

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N
Chicago
1 review
Dined on August 12, 2018
Overall 4food 3service 3ambience 4

This was my second visit. Our first visit was wonderful and so we decided to come back. Unfortunately, the food was not as we had remembered it. Filet mignon was too rare for my taste and food wasn't hot when it arrived at the table. However, the waiter was very nice and accommodating, as we had a service dog with us.

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F
Washington DC
9 reviews
Dined on August 10, 2018
Overall 5food 5service 5ambience 5

I have been wanting to try Homestead on the Roof. It did not disappoint! Amazing atmosphere and FOOD! Love the Farm-to-table concept. They knocked it out of the park. Cannot wait to share with others! So many options for all.

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OE
Chicago
1 review
Dined on August 8, 2018
Overall 4food 4service 5ambience 5

It was my boyfriends birthday so i wanted a lovely rooftop and that’s what i got. Our server Teddy was incredible and the food was delicous. There are definetly better restaurants with better food but with the lovely patio and fresh ingredients it was definetly memorable.

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J
Chicago
4 reviews
Dined on August 4, 2018
Overall 4food 5service 4ambience 5

I love coming here! The food and drinks are amazing and the ambiance on a warm Chicago night is the perfect combination.

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JO
Chicago
5 reviews
Dined on August 4, 2018
Overall 2food 2service 2ambience 2

Very disappointing tonight...we have been there before, but tonight was a big disappointment. It took 30 minutes to take our appetizer order. They were out of one of the main appetizers at 8:00 pm...pretty early in the evening. Also, only 5 red wines on the menu, and again they were out of the best reds on the menu.

The kitchen must have been off tonight. The Italian steak tartare was under seasoned. The table next to us was complaining about the rib eye. We had a party of 4, and after waiting 1 and 1/2 hours, one of the dishes did not come out with the rest. My chicken was over done and dry. Everyone at the table only ate half their meal. It just wasn’t that good.

I hate to write such a harsh review, but the kitchen really failed us tonight.

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JD
Chicago
1 review
Dined on August 4, 2018
Overall 3food 4service 1ambience 4

It is difficult to say that I would recommend this place to a friend. Basically, the food is good, but the service is extremely slow and it takes away from the enjoyment of the evening because you feel like you are always waiting. Also, on the night we were there, they ran out of the pea soup and the grapefruit juice needed for two of the four drinks that we wanted to order. It seems that whomever is managing is not focused on the experience of the guests dining. I have been there 2 times in one month. May give it another try sometime, but it will be a while before I go back there

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DG
1 review
Dined on August 3, 2018
Overall 4food 4service 4ambience 5

Truly enjoy the experience @ Homestead. The food was great. The service was great. I would love to eat here in early fall season. I've already recommended Homestead to several freinds...

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DD
Chicago
2 reviews
Dined on August 3, 2018
Overall 5food 5service 5ambience 5

Super friendly waiter, food was great and came out quickly!

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s
Chicago
71 reviews
Dined on August 1, 2018
Overall 5food 5service 5ambience 5

I love Homestead so much I ate there twice in one week. There are plenty of options that change seasonally so there is always a reason to go back and the rooftop has the best ambiance. When it started to drizzle they quickly got us seated inside to continue our meal. Great staff!

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OT
Chicago
2 reviews
Dined on July 28, 2018
Overall 1food 3service 1ambience 3

Our reservation was for 8:30 and we didn’t get seated until 9:15. Then we didn’t get drinks for another 15 minutes. The server and the hostess weren’t apologetic about the wait and actually mocked us re: how long we’d been waiting. I had been waiting to try this place with my out of town guests and was embarrassed. For a place that requires a credit card to book a reservation, you’d think they’d be more professional. Get a new hostess.

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S
Chicago
31 reviews
Dined on July 28, 2018
Overall 2food 3service 2ambience 3

The idea of the restaurant (farm to table rooftop escape) did not meet the execution.

Upon arrival, the staff seemed a little confused. Our table was not ready and they scrambled to put something together. When we were seated our table was covered in water. That set the stage for a number of other issues throughout the night for which the staff was totally unapologetic.

The food, in general, was lackluster. The halibut had a pork sauce hiding on the bottom, although that was not disclosed on the menu, and our table was pescatarian. One in our party asked for a mocktail that was not citrusy, and was brought a sparkling lemonade because the bar was "too busy to make anything else". I'm not sure how a savory caraway seed pretzel was included in a bread basket who's only fat was a honey butter (yuck!). The smores dessert was a chocolate pie on a smear of coconut cream (name it something else folks.)

If we had only had one of these issues or if the staff seemed to care at all (especially about the fish!!) I might have given Homestead more stars; it's a pretty place and we love the associated Roots Pizza and West Town bakery. But I could not recommend wasting your time here when there are so many other options in the city.

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