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  • Homestead on the Roof

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Homestead on the Roof
Homestead on the Roof

Homestead on the Roof Details

  • Dining Style: Casual Elegant
  • Website: http://www.homesteadontheroof.com
  • Phone: (773) 332-2354
  • Hours of Operation: Dinner: Sunday, Tuesday, Wednesday, and Thursday - 5pm thru 10pm.
    Dinner: Friday and Saturday- 5pm thru 11pm.
  • Payment Options: AMEX, Diners Club, Discover, MasterCard, Visa
  • Cuisine: Contemporary American, Organic, Wine Bar
  • Executive Chef: Chris "Chip" Davies
  • Dress Code: Casual Dress
  • Accepts Walk-Ins: Yes
  • Additional Details: Bar Dining, Bar/Lounge, Beer, Farm to Table, Fireplace, Full Bar, Late Night, Non-Smoking Restaurant, Patio/Outdoor Dining, Personal wines welcome, Personal wines welcome (corkage fee applies), Private Room, View, Wine, Wine Bar
  • Private Party Facilities: Homestead is available for private dining and buyouts. Our culinary team will work with you to craft menus to fit your specifications.
  • Private Party Contact: Kate Uhe (773) 332-2354
  • Entertainment: None
  • Special Events & Promotions: For special events, please email Kate Uhe. KateUhe@thefifty50.com
    Homestead on the Roof is the perfect venue for office parties, weddings, and holiday events. We will be staying open throughout the year and will be booking the rooftop deck and inside small and large events.

Getting there

  • Cross Street: Winchester (ENTER THROUGH ROOTS PIZZA)
  • Public Transit: Damen Ave "50" CTA bus. Chicago Ave "66" CTA bus.
  • Parking: Valet
  • Parking Details: We offer valet parking and street parking is also available.
A word from Homestead on the Roof

Homestead is a literal farm-to-table restaurant featuring rustic, yet elegant cuisine from executive chef Chris "Chip" Davies; specialty cocktails, wines, spirits, and beers from beverage director Patrick Henaghan; and desserts and breads from executive pastry chef Chris Teixeira.

New for Summer 2014 is a retractable awning for outdoor dining during rainy days.

The rooftop patio of Homestead features 80 outdoor seats with full views of our L-shaped 1,000-square foot organic rooftop and vertical hanging gardens. There is over 2500 square feet of edible produce and herbs which is incorporated into all of our dishes and cocktails.

The light-filled second-floor interior air-conditioned room at Homestead features an additional 60 seats at tables and another 12 seats at the bar.
Foodspotting photos
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Awards voted by OpenTable diners
  • Diners' Choice WinnerContemporary American
  • Diners' Choice WinnerOutdoor Dining
Diner Reviews
  • "Homestead's roof top patio is just lovely and surprisingly quiet since Chicago Ave. is such a busy street. Four of us shared 2 appetizers, 2 medium plates and 2 large plates. The stars of the evening were the AGNOLOTTI and the SEARED WALLEYE. We didn't order the BREAD BASKET and will the next time. It looked wonderful and we would have loved to use it to sop up the wonderful broth in the WALLEYE. We really enjoyed the BEIGNETS for dessert. We shared a bottle of the Scarbolo, “Ramato” Pinot Grigio, Italy and loved it. The wine list is very interesting but is pricey so this will be a special occasion destination for us. Our waitress was outstanding. She answered dozens of question and gave us excellent guidance."
    Dined on 7/10/2014
  • "Very nice outdoor roof setting. Eclectic menu. The foie gras and grilled walleye with lobster and gnocchi are winners."
    Dined on 7/10/2014
  • "I brought a group of friends here from out of town. I had been one time before and really enjoyed it. I loved the outdoor seating area and the food was great. But we experienced the worst service when we went back for the second time. I felt terrible for the out-of-towners because there are so many fantastic restaurants in Chicago and I took them somewhere a little different than the typical Chicago favorites. It was a complete let-down. The waiter was never around. We had to hunt him down to get more wine. In the end we just ordered a couple bottles at once. The food took forever to come out. There was a very very long wait between appetizers and entrees. I wouldn't be surprised if he forgot to put the order in. I won't be back."
    Dined on 5/25/2014
  • "I've read some reviews that weren't very positive about this restaurant, and I completely disagree with the naysayers. Our service was excellent. Our server suggested a dish that we loved, he was very attentive, and the food came out quickly. Everything was very fresh and I love that they use the herbs and veggies they grow right there. Well done!"
    Dined on 7/9/2014
  • "To start it took about 10 minutes for our waitress to come over and offer water. She came back about 10 minutes later to take our order. We ordered a drink, 2 appetizers and 2 entrees/main dishes. We waited for another 15 minutes before she came back to tell us that the bartender was particular about his drinks. She brought the drink back a few minutes later. We then waited 15 minutes for appetizers. They were very good but mine was not hot. We saw our waitress at other tables but she never cam back to check on us while we waited for our entrees. We waited another 25 minutes before those came. Again, delicious. While we waited for our entrees we ran out of water. No one came and checked and refreshed us. Good food but poor service."
    Dined on 7/5/2014
  • "roof was so cute, perfect for a dinner for two. we just got apps and drinks but the food was awesome!"
    Dined on 7/1/2014
  • "We were disappointed that we were not able to sit outside, but the inside is nice as well and has an open and airy feel. The service is friendly, knowledgeable, and attentive. Our dinner this time was not as outstanding as the first time I ate here, but the drinks and small plates made up for it. I look forward to returning to Homestead!"
    Dined on 7/5/2014
  • "We started our holiday evening with guests from the Burbs at Homestead. After an afternoon in the sun, it was lovely dining amid the rooftop garden on a beautiful evening. The stylish heat lamps absorbed the chill nicely leaving us all quite comfortable. All of the food is scrumptious. We highly recommend starting with the bread basket. From there each of us had our favorites... mine was the soft shelled crab, but others in our group were savoring the scallops and the short ribs. The service was stellar!"
    Dined on 7/4/2014
  • "A little chilly but accommodating staff brought us cozy blankets. Loved seeing garden. Seating was comfortable; tables are spaced so people can have a private conversation--thank you! Wished the vegetable options were more intriguing but the ones we were tried were well prepared. Everything fresh and tasty. Chicken entree was wonderful. Rhubarb dessert was too small to share."
    Dined on 7/3/2014
  • "My boyfriend and I met here a year ago and celebrated our anniversary at this visit. Everything was amazing. Spectacular food, amazing drinks, and superb service. I love this place."
    Dined on 7/2/2014
  • "I absolutely love this place. This week was my second time eating at Homestead and it was, remarkably, even better than the first. I went with my family and the four of us split the bread basket, tomato salad, chicken skins, walleye, chicken, sweet corn agnolotti, and beignets for desert. Each dish was better than the last and the flavors were surprising and unique. Not to mention the fabulous gin and tonics and the romantic view of the gardens. Would recommend to anyone and I will be going back as many times as I can until I've tried everything on the menu!"
    Dined on 7/1/2014
  • "We were really disappointed. Made a reservation for 8 people over a month ago. It started to rain right as we got there. We waited an hour and a half and still weren't seated for our reservation yet we saw several parties get sat before us. They claimed they only had two larger tables and so we would have to wait and couldn't give us any idea how long. However, when we paid them $100 to be seated an hour and a half late from our RESERVATION, they were able to easily push two tables together for us (why didn't they do this earlier without us having to pay them to do so???). I was really bummed they were not able to handle this better."
    Dined on 6/28/2014
  • "Can't imagine anything better than sitting in the sunshine eating unbelievable food and having unique cocktails all the while viewing the city from a rooftop. Never had a better meal or more friendly service. Great job . We will be back. Thanks for a truly unique night for my wife and I."
    Dined on 6/27/2014
  • "Our waiter Ryan was amazing!!!! Food was very good to great!! Love the rooftop deck!!"
    Dined on 6/27/2014
  • "Great service and great food. I'm a vegetarian and they were very accommodating. great cocktails. yummy desserts. highly recommend it."
    Dined on 6/24/2014
  • "The food was great!! I will definitely be returning for the chicken skins! If Jennifer is working, ask to sit in her section. She's fantastic!"
    Dined on 6/25/2014
  • "If you are looking to dine outdoors, this spot is tough to beat! However, food didn't deliver on my expectations for the cost. Everything was "ok", but in Chicago, "Ok" is not good enough!"
    Dined on 5/30/2014
  • "It was very quiet for a Thursday happy hour on a rooftop in nice weather... BUT drinks were great! The Cucumber Gin cocktail was great! The ice cubes were are from the cucumber and the blueberry rum drink seas super refreshing and yummy!"
    Dined on 6/26/2014
  • "We loved the food--blown away by the mussels, the pappardelle, and especially the s'mores dessert, we could eat that spice cookie ice cream by the bucketful! Our server was attentive, knowledgeable, and fabulous. We didn't get to eat outside because of the rain, but don't worry we'll be back! We were so impressed. The food was fabulous. We'll definitely be taking our friends and family here."
    Dined on 6/20/2014
  • "Menu was distinctive with a variety of options. Food was excellent. The rooftop was closed due to rain, but the inside dining is adjacent to the outside seating, with a wall of windows, so it still felt like an outdoor atmosphere. The gardens looked awesome. We had a party of two, on a Thurs. evening w/ 8pm reservation and it was packed full of people and beyond loud. It is obviously a hot spot; unless our experience was unusual, don't expect to be able to have a quiet conversation - even with just a party of two."
    Dined on 6/19/2014
  • "The hostess melanie was prompt in seating my girlfriend and I. Our waitress was nice, but never introduced herself, forgot an appetizer, but otherwise wonderful and accomodating. Food and cocktails were delicious and I will be coming back to the restaurant soon."
    Dined on 6/17/2014
  • "This is our third time and had a wonderful time. We ate outside and it was fabulous. I would say we love the gem salad but a tad too much dressing on black barley. The duck two ways was fine but not as great as the other 3 entres that were ordered. The GM, Kate, is great and remembered that we ate there 2 times before, came over and gave us info on new offerings since we had been there."
    Dined on 6/17/2014
  • "Some reviews said they didn't feel the service was good... we had a superb experience from the hostess to the bartender to our top notch server. The food was ON POINT. Very tasty and not overly ornamental, yet beautiful. Chef seems to have found the perfect balance. We actually ended up eating indoors due to a pending thunderstorm so I can't speak to the rooftop but the indoor ambience was really great. All in all this place has a great vibe and I'm glad to have finally tried it. Will definitely be back.... a lot!"
    Dined on 6/15/2014
  • "large group graduation dinner. adventurous creative dishes prepared well. all winners. waitstaff were superb. winelist limited but can order excellent bottles off of the by-the-glass list."
    Dined on 6/14/2014
  • "Sat on the roof. Food was excellent - farfalle, walleye with incredible gnocchi, duck two ways. Highly recommend."
    Dined on 6/14/2014
  • "Food is wonderful & the outdoor area is perfect! Our service was just ok and The food is a bit pricey for what you get, but I would go back because the of the tasty food and ambience."
    Dined on 6/12/2014
  • "The food was great and we couldn't complain. We both enjoyed it, but it's not something to write home about. The large plate we ordered wasn't as large as we thought and the dessert was okay. The food is good, the atmosphere is great, and the service was great as well. Good restaurant with okay food. The drinks are amazing! Hands down great drinks! Overall, we would go back, but not on a regular basis."
    Dined on 6/6/2014
  • "While the food was was delicious, the dishes are NOT share friendly. They need to ditch this concept and focus on quality food and great ingredients or get the "share" concept right. They tried to adopt a "sharing" approach that's inappropriate for the dishes and portions. Would be a better menu if they abandoned this theme and let people share if they wanted to but for god sake dont have the waiters force it on people. A single croquet with a fried egg is very awkward (and kind of gross) to share with four people (our waitresses recommendation). And no serving spoons provided! Similar issues were present throughout the meal, pasta portions were enough for one bite each. Large plates were perfect for one person but very strange for sharing."
    Dined on 6/7/2014
  • "Really great food, but the service was a little lackluster. "
    Dined on 6/3/2014
  • "The service was slow to start. We had to wait forever to get a cocktail menu, but once things got started everything was great. The desserts were amazing and so were the chicken skins. We would definitely go back."
    Dined on 6/1/2014
  • "For a restaurant with a story to tell (the over-used "farm to table"), a pretty pricey menu, and a limited and mostly expensive wine list, they need to do a better job of putting what they do in context and being more attentive to diners. The outdoor rooftop space was terrific on a beautiful evening (though with lots of ambient noise due to its urban setting), but could be challenging otherwise."
    Dined on 5/31/2014
  • "Great cocktails, food and wonderful service. Our server had a great knowledge of wines when we switched we wanted a glass with dinner. We will be back again."
    Dined on 5/30/2014
  • "We had great weather for this rooftop restaurant, which made all the difference in enjoying your time at Homestead. We ordered the bread basket, the pappradelle, and the half chicken, which were all "winners." I would definitely come back, especially on a nice summer night. "
    Dined on 5/25/2014
    Dined on 5/8/2014
  • "The food is top notch- white cloth-michelin star quality- but the ambiance is too casual for the level of plating and food- the chef will be forced to leave because the hostess- waitstaff aren't really at his level. we had a open table reso- they gave our table to a group who moved to it before we sat down and they left us with literally no option but to sit inside by ourselves near the door where the staff went in and out of every 5 seconds. The hostess is not in command of her post- dressed sloppily and didn't know how to handle the rogue diners. 260.00 later on a Thursday night. Can't recommend. but wow the chef is a superstar."
    Dined on 5/29/2014
  • "I've eaten here before and knew that the food would not be disappointing. My only complaint is that I specifically came here to eat on the patio. I noted it in my reservation request and when I talked to the hostess to confirm our reservation again requested that we be sat outside. She mentioned that it was first come first serve but they should be able to accommodate us. Upon arrival, we were told there was no room on the patio. The inside is nice however it was quite awkward as there was only one other table in the dining room. After everything we were able to have our dessert outside, which I was quite please by, I just wish we could have had the whole evening I had planned on and was so excited to share with my boyfriend. "
    Dined on 5/25/2014
  • "We are two vegetarians going to not the most veggie-friendly restaurant- but the chef made us a special veggie entree to share which was so appreciated and delicious. Great service, beautiful patio, loved it!"
    Dined on 5/24/2014
  • "Stumbled onto the place by searching on-line for restaurants in the area. Food was fantastic! Creative blends of flavors and great presentation. The bread basket was wonderful, as were mussels, walleye, duck. Not a terribly deep wine list, but the sommelier indicated she's constantly bringing in new stuff. Ran out of the wine we'd ordered after the first bottle and she did a great job of figuring a replacement which was (unknown to us at the time) cheaper than the original. Great beignets finished of the night. We'll be back. "
    Dined on 5/24/2014
  • "Summer is coming and it was great to spend a Saturday evening in May dining on the patio at Homestead on the roof! Fun place, warm enough with some patio heaters and an open fire (even some Blankets offered if you are cold) Food was nice, service was good - but Desserts were amazing, would go back just for them. "
    Dined on 5/24/2014
  • "Each dish was more scrumptious than the prior one. One bite and each of the members of my party smiled with bliss. My only suggestion would be to serve spoons and bread with the meal to soak up every drop of the delectable sauces/broths of each dish. We had and recommend the half chicken, the short ribs, and the walleye. "
    Dined on 5/17/2014