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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
  • "I have previously been to Homestead "On The Roof" and dined outside. They said they didn't use the inside unless it rained. I then booked through top table for my husbands 30th as his parents are in town. They only had a late table and when we arrived, very hungry, they told us we would be dining in doors. This really shocked and upset us as the whole idea was to dine "On The Roof". By now it was late and we couldn't really find elsewhere to eat. We hesitantly took the offer given and it got worse. It was FREEZING and our mum was wrapped up in a scarf and cardigan. We didn't bring layers as it was hot out and we thought we'd be outside. The was NO atmosphere what so ever but a very loud party to make conversing difficult. A ruined bday."
    Dined on 7/18/2014
  • "Food was outstanding and portions were good on all but the large plates. Craft cocktails were also excellent. Wine list by the bottle is a little pricey for the selections. Would return for a cocktail and appetizer."
    Dined on 7/18/2014
  • "The vegetarian option was awful. I had everyone at my table try it and everyone thought it was gross. I was so excited to try out this restaurant and was very disappointed. I understand that their menu is 95% meat, but you would think for a farm-to-table restaurant, they would have a rockin vegetarian option."
    Dined on 7/17/2014
  • "We came as a couple to eat. First time. Atmosphere was great; charming, romantic, lush and green. Service was fantastic and attentive. Portions were a BIT small, but excellent."
    Dined on 7/17/2014
  • "Every dish we tried was unbelievable. I cannot give the chefs here enough praise. Cocktail list and wine selections are excellent. Every staff member was friendly, competent, extremely knowledgeable. Service was immaculate. Rooftop seating area is stunning. I will definitely be coming back!"
    Dined on 7/15/2014
  • "We could not have asked for a more enjoyable evening. The weather cooperated with our plans as well. Beverages were on point. Our friends differ in beverage tastes and all were happy with specialty cocktails and wine. Thank you Patrick! Appetizers...mmmm. Chicken skins and sriracha sauce!!! Bread basket and cinnamon butter!!! Don't miss out on the pastas, pappardelle is a must. Ended our meal with a tasty array of desserts. Our favorites include but are not limited to the adult freeze pops and the deconstructed s'mores. Can't wait to bring other friends! Thank you Kate for a memorable dinner. Oh, end your night with a pickleback"
    Dined on 7/13/2014
  • "Nice quiet restaurant, great place place for a date night."
    Dined on 7/12/2014
  • "Amazing food and wonderful experience! All of the recommendations from our server were spot on. From cocktails through dessert we enjoyed every last bit. While we want to try the entire menu, we will definitely order the soft shell crab and smores again in the future."
    Dined on 7/12/2014
  • "The food was amazing, our server was extremely knowledgable about the menu items, and the outdoor dining experience was very unique. We sat right next to the rooftop garden and it added to the ambiance by knowing we were eating locally (like hyper-locally) sourced food. Truly is one of the most unique dining experiences we have had in the city!!"
    Dined on 7/11/2014
  • "Very nice outdoor roof setting. Eclectic menu. The foie gras and grilled walleye with lobster and gnocchi are winners."
    Dined on 7/10/2014
  • "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
  • "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
  • "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
  • "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
  • "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
  • "The garden is great in the summer (if you get seated outside), but inside -- we froze our tuchas off. Brrrrrrrr. Food was good, could use a little more food on each plate, though. Overall, was good. I'd go back."
    Dined on 6/28/2014
  • "Our waiter Ryan was amazing!!!! Food was very good to great!! Love the rooftop deck!!"
    Dined on 6/27/2014
  • "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
  • "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
  • "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
  • "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
  • "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
  • "Sat on the roof. Food was excellent - farfalle, walleye with incredible gnocchi, duck two ways. Highly recommend."
    Dined on 6/14/2014
  • "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
  • "Very disappointed the second time I came here. Extremely slow service. Food portions were drastically cut since the last time I had been there and the food was not flavorful."
    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
  • "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
  • "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
  • "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