Homestead on the Roof

4.5
522 reviews
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$31 to $50
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Contemporary American
Top Tags:
  • Good for a Date
  • Romantic
  • Neighborhood Gem
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 Scott Shulman.

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.
Dining Style
Casual Elegant
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Cuisines
Contemporary American, Tapas / Small Plates, Farm-to-table
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Hours of operation
Dinner
Wed–Sun 5:00 pm–10:00 pm
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Phone number
(773) 332-2354
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Payment options
AMEX, Diners Club, Discover, MasterCard, Visa
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Dress code
Smart Casual
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Executive chef
Scott Shulman
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Private party facilities
One of the city's best rooftops with a spectacular garden, cobblestone fireplace, rustic candlelit chandelier, & vine-climbing pergola with a retractable awning, Homestead is a premier year round destination for your most special events and corporate buyouts.
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Private party contact
Jacklyn Seaverns: (312) 479-2529
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Catering
Homestead on the Roof does have the capabilities to cater outside events and venues. Please email Jacklyn Seaverns for more information.
Jacklyn@homsteadparties.com
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Neighborhood
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Cross street
Winchester (entrance is through ROOTS HANDMADE PIZZA)
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Parking details
Metered parking available all along Chicago Avenue & Winchester.
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Public transit
Damen Ave "50" CTA bus. Chicago Ave "66" CTA bus.
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Entertainment
None
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Special events & promotions
For special events, please email Jacklyn Seavern, Jacklyn@homesteadparties.com
Homestead is available for private dining and buyouts.
Our culinary team will work with you to craft menus to fit your specifications.
We do have catering menus for all types of price points and options that include chef stations, plated dinners, and open bar.
Please email Jacklyn for a copy of our menu and we will set a time to discuss a custom menu with our Chef Team.

Homestead on the Roof also caters for larger outside venues at The Bridgeport Art Center, Baderbrau, The Rookery and Studio Manarchy.

Additional information can be found on our website, www.homesteadontheroof.com
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Gift Card
Additional
Banquet, Bar Dining, Bar/Lounge, Beer, Cocktails, Fireplace, Full Bar, Gluten-free Menu, Non-Smoking, Outdoor dining, Private Room, View, Weekend Brunch, Wine

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 522 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
4.4
service
4.7
ambience
4.0
value
Noise · Moderate
89% of people would recommend it to a friend
5
4
3
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5.0Dined 2 days ago

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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5.0Dined 4 days ago

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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4.0Dined 5 days ago

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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4.0Dined on August 13, 2018

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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5.0Dined on August 10, 2018

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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4.0Dined on August 9, 2018

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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4.0Dined on August 5, 2018

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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2.0Dined on August 5, 2018

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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3.0Dined on August 5, 2018

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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4.0Dined on August 4, 2018

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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5.0Dined on August 4, 2018

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

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5.0Dined on August 2, 2018

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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1.0Dined on July 29, 2018

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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2.0Dined on July 29, 2018

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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5.0Dined on July 28, 2018

Great outdoor roof patio with its own garden. Literally watched the chef step into the garden for ingredients. Shareable portions. Great cocktails too. It’s a rooftop on a busy street so it has street noise (as expected).

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4.0Dined on July 27, 2018

GET THE BREAD!
Everything else we got was lackluster.

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5.0Dined on July 26, 2018

My new favorite place. Great food and excellent service!

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5.0Dined on July 22, 2018

Everything from the service to the food was top notch. Literally could eat the Brussel Sprouts as a main course both because of the deliciousness and size. Other recommendation is the Surf n Turf appetizer- ordered this for main course and it was absolutely perfect!

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5.0Dined on July 18, 2018

Lovely roof-top dining with rustic farm to table decor. Attentive, well educated staff. Flavors of food were bright and original with unusual combinations. While sharing was encouraged, portion sizes were small for our table of 3.

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1.0Dined on July 15, 2018

The food was bland and overpriced.
$15 for a 1/4 head of cauliflower?! Sides that arrived 15 minutes before our food. And a bread platter that was stale.
We tried to share our feedback with Kat, who responded with the most disgusted face of discontent I’ve ever seen. So much for valuing the input of a customer who wants to see you succeed. The graveyard of Chicago restaurants will soon be seeing Homestead join them. What a shame.

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5.0Dined on July 14, 2018

Unique atmosphere. Unique farm to table concept. Great tasting good

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3.0Dined on July 14, 2018

Great setting on the roof. Food was ok, not great. Skip the bread - it was dry and not very tasty.

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5.0Dined on July 14, 2018

Amazing food, service and ambience. Great for a birthday celebration or date. Absolutely will recommend

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5.0Dined on July 13, 2018

Very nice atmosphere and fantastic food

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4.0Dined on July 8, 2018

Great food and ambiance. Our reservation was at 8pm and 3-4 items on the menu were sold out by the time we ordered. That was very disappointing, but what was more confusing and disappointing was that a large party came as we were paying our bill and got four servings of one of the dishes that we were told was sold out less than 2 hours prior.

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5.0Dined on July 7, 2018

Wonderful experience. Food was excellent!
Server was amazing.. wes fest was going on so difficult to get to and very loud Street festival. I will be back!

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5.0Dined on July 7, 2018

You can't beat the vibes on the roof of Homestead next to the garden where they grow the food you're eating. The staff is always really friendly and the cocktails are amazing.

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4.0Dined on July 7, 2018

The DJ event that weekend was distracting and didn’t make it the experience we were looking for but they did the best they could provided.

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5.0Dined on July 6, 2018

Read about this place when researching neighborhoods in Chicago and it was my favorite restaurant that my wife and I visited while on vacation. Great food, service, and ambiance. Staff is very knowledgeable about their food and I don’t see how they couldn’t love it.

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5.0Dined on July 6, 2018

It was delicious. We ordered a variety of appetizers and small plates, and split an entree, the Filet mignon. The ambiance on the roof is very relaxing. Good for dates, or bringing your parents when they’re visiting!

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5.0Dined on July 6, 2018

First time dining on a roof and it was very nice!! Our server was so pleasant and she had a smile on her face the whole time. So sweet. Had a blast.

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5.0Dined on July 2, 2018

Food was really amazing, and the workers were amazing!

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4.0Dined on June 30, 2018

We had a delightful experience! The staff was friendly and attentive...easy to engage in conversation and answered all our questions eagerly. My husband had the pork chop which he said was the most tender he has ever experienced. I had the filet cooked to perfection. We both could not get enough of the pad Thai Brussels sprouts!!! Omg!! They were amazing!!! Our only regret was we had no room for dessert... maybe next time....
We were given a complimentary glass of champagne for our anniversary... so very thoughtful... thank you!

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3.0Dined on June 29, 2018

The ambiance and vegetables & herb garden are lovely. The bread basket and brussel sprouts were delicious. But the main entrees: the sauce the scallops were in tasted like sea-mud that had turned - inedible and very disappointing given that I'd been looking forward to it and $33. The pork chops were almost tasteless - virtually no seasoning, just slabs - although the rhubarb pie was lovely. And the desserts were a serious disappointment: the banana that was chocolate covered was either way overripe or cooked; the s'more tasted great but was so tiny, it was difficult to share. It would be a great place to stop for a drink and appetizers but I absolutely would not recommend it for the mains.

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5.0Dined on June 28, 2018

We dined with friends on a beautiful Thursday evening. The gardens are lovely as are the walls of flowers on the Roof. We ordered and shared heavily focused on the vegetables all of which were amazing. Both beautifully served and unusually presented. Our Waitress was delightful and helpful but not pushy which I appreciate. We finished with the Halibut and then had no room for the s'mores so we will have to go back

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4.0Dined on June 24, 2018

There were some good things and bad things. Gave my drink to my friend and gave me hers, once we figured it out, we kept it that way and I got my original for my second drink. No biggie but kind of annoying. Really cute spot, loved the garden and rooftop and the decor (they are going to have trouble with the mint planted in the ground! gonna take over everything. but it was good in my cocktail :)
The food was OK. envious of my dinner mates that chose the halibut dish, I ordered the hokkaido scallops which were cooked nicely, but the accompaniments were very umami heavy and it wasn't my favorite thing. The bread basket was delish but the herb oil was very salty and hard to get the spreads out of the cute mason jars. Boyfriend orderd the pork chop that was super thick, dry except for the meat near the bone. The sausage pie was good, but kind weird and hard to eat. The whole experience was like that. Some good, some bad. I don't think I'd go back, but it was fun to try.

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5.0Dined on June 23, 2018

Great meal, wonderful service.

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5.0Dined on June 23, 2018

I have lived in Chicago all my life and have Dunedin many Chicagos best restaurants over the last 40 yrs. Both my girlfriend of 6yrs and I believe the Roof top dining was the most romantic and perfect outdoor spot we have ever been to. Perfectly shaded and the food was fantastic.

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5.0Dined on June 23, 2018

Absolutely amazing! Love the food, ambiance, and service! Perfect date place for a beautiful evening in Chicago!

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3.0Dined on June 22, 2018

I was disappointed the bread basket and some wine was out. After having to confirm restvs with a CC I would assume they know the numbers coming forward. That was frustrating.

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