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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
  • Email: kateuhe@thefifty50.com
  • Phone: (773) 332-2354
  • Hours of Operation:

    Dinner: Wednesday through Sunday 6pm until 11pm
  • Payment Options: AMEX, Diners Club, Discover, MasterCard, Visa
  • Cuisine: Contemporary American, American, 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
**PLEASE NOTE** ALL PATIO SEATING IS FIRST COME FIRST SERVE. OUTDOOR SEATING IS NOT GUARANTEED.

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 Benjamin Schiller; and desserts and breads from executive pastry chef Chris Teixeira.

The rooftop patio of Homestead features 80 outdoor seats with full views of our L-shaped 1,000-square foot organic rooftop farm and two massive vertical hanging gardens.

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.
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Foodspotting photos
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Awards voted by OpenTable diners
  • Diners' Choice WinnerContemporary American
  • Diners' Choice WinnerFit for Foodies
  • Diners' Choice WinnerOutdoor Dining
Diner Reviews
  • "Homestead on the Roof can be found through a pizzeria and up a steep flight of stairs. As i am disabled and use a cane the stairs were a challenge. "This better be worth it," I muttered to myself. Wow! It was certainly worth it and I would confront those stairs in a flash if it meant I could dine there today. We all loved everything we ate. We began with the kale salad and breadbasket, progressed to the duck egg carbonara and the beef short ribs, then on to the duck two ways and the seared walleye. To say that we savored every bite was an understatement. Our service was impeccable. All members of the serving staff were both friendly and professional. It was terribly noisy however."
    Dined on 4/4/2014
  • "We had a great experience, the manager Kate actually was our server. She was very knowledgable about the food and the beverage program. We will return."
    Dined on 4/6/2014
  • "We came from out of town with a group of 6, the manager herself served us for the evening, and was incredibly helpful and knowledgeable--you can tell they're passionate about their food and the experience they create. The deck wasn't open yet (but looked like it would a fantastic spot to hang out in the summer) so were seated in the enclosed dining room with exposed brick and soft lighting. We ordered a mixture of small and big plates to share, plus all of the desserts. Everything was wonderful--standout favorites were the chicken skin and the kale salad. Everyone loved their cocktails as well. Their menu changes often with the food they grow on the deck, so would love to come back for more."
    Dined on 4/4/2014
  • "Great ambiance, delicious food. A lovely experience that I have already recommended to my friends. My husband especialy liked that it was kind of a trick to find the restaurant. It made us feel like we were "in the know.""
    Dined on 3/29/2014
  • "My girlfriends get together every month for dinner and this month I picked Homestead on the Roof. Overall it's a great restaurant. We loved the ambiance, food, and wine. The only big problem we had was that 2 of us ordered the steak and it was way too tough and grisly (the cut was a ribeye but still….it was pretty bad). We could not cut it let alone chew it. We didn't complain but we didn't eat it so when the waiter saw this he asked how the food was and we told him. When he brought the bill he informed us that he had removed both steaks from the bill. All of us were impressed and it will keep us coming back. Everything else we ordered from appetizers to desserts and wine were outstanding. Try the outdoor deck in the summer- beautiful!"
    Dined on 3/29/2014
  • "Homestead is a great find. The indoor space feels rustic and cozy (still too cold to sit outdoors!) and the food was phenomenal. We had consistently interesting and tasty small plates, with no disappointments in the mix. Prices were reasonable, especially given the high quality of the food. The service was helpful, friendly, and attentive. I'd go back in a heartbeat!"
    Dined on 3/26/2014
  • "extremely nice restaurant. dining room had a homey feel-beautiful and well laid out. loved the tables made from refurbished doors. servers friendly, polite and knowledgeable-enhanced our experience. food, drinks were inventive, but not too different from the norm. would definitely go back."
    Dined on 3/23/2014
  • "Went for Chef's week. Might be best meal I've had in Chicago. Chris Davies is doing amazing things in the kitchen. I cannot stop thinking about the crispy duck leg. I will be back often and am looking forward to eating on their roof when winter finally ends here."
    Dined on 3/19/2014
  • "We have been wanting to come to Homestead for quite awhile. Finally made it there. Actually just down the street from our home. Great room, great service, excellent food. Salads were full of flavor(s) . We had the little gem and kale. Walleye was cooked perfectly, the chunks of lobster in the sauce were tender and the gnocchi melted in the mouth. The smoked duck was another hit with excellent stone ground mustard. The bread basket was a nice started with the accoutrements was worth it. You could get gratis bread (rarely this good, nor the variety) and pay the same for the sides that come with it. Looking forward to our next time dining at the Homestead."
    Dined on 3/13/2014
  • "We went for Valentine's Dinner, we were from out of town so I was a bit disappointed I couldn't order from their regular menu and had to go with the set meal. But it turn out great!! It was a three course meal that came with wine pairings, and they gave us surprise treats in between which wasn't mention on the menu. It was very romantic to have dessert that came out with dried ice bubbling and steaming and crystallize rose petals. Food was great, service was excellent the chef came out to explain each dish. And in the summer you can seat out on the roof top patio. Great place to take a date, sure to impress."
    Dined on 2/14/2014
  • "We had a great experience at Homestead. The Weston - a bourbon cocktail with the essence of pipe tobacco- smells of maple and goes down smoothly. The walleye dish with gnocchi and shrimp was also exceptional."
    Dined on 2/27/2014
  • "We picked this restaurant as we wanted a reasonably priced fit for foodies restaurant that was cozy with tasty food for a snowy evening. We were not expecting to have one of the nicest evenings we've ever had in a restaurant and we go to lots of restaurants. Kate the Manager and our server was knowledgable, friendly and really took "ownership" of making our experience great. The food was unbelievable. Beautiful presentation, creative and tasted exquisite. We can't wait to go back and especially want to try it in the summer on the roof. Even in the winter, it had the fire lamps going so it seemed like fire places all around and was charmiing."
    Dined on 2/15/2014
  • "We went to Homestead on the Roof the day after Valentine's Day to celebrate. We were sat by the window with a burning torch outside, so it had a similar romantic glow of sitting near a fireplace. We both ordered from the three course menu. The bread and spreads were a delicious way to start, as was the amuse bouche. We enjoyed our salads and wine pairings and were blown away by our lobster entree. It was small, but well-prepared and delicious. Our desserts were almost too beautiful to eat and also tasted great. Our server was knowledgeable, attentive, and friendly. I am so glad that we found this place and I'm looking forward to going back and sitting outside once it has warmed up!"
    Dined on 2/15/2014
  • "A cozy environment for dinner, with friendly waiters, and an eclectic restaurant week menu. Had dinner with four friends, so we were able to make the most out of the three course prix fix menu, w/ pairings. Food was creative, duck egg salad, kale salad, and curry quinoa/cauliflower. Main courses - mussels were delightful, pasta was delicious, and sweetbreads were cooked perfectly. Dessert brought down the house - an absolutely magical mouthwatering experience (lemon, beet, or chestnut!) Staff was attentive, until it came time to pay the bill. We left feeling sated, but I think if we weren't four girls, we'd still be hungry. Wonder if portion size on main dishes increase on regular menu? Looking forward to visiting in summertime!"
    Dined on 2/6/2014
  • "Food was delicious. Our server was not attentive and rude. We were seated near the front and so every time a new person would enter the restaurant, we got caught up in the cold draft. Overall, we enjoyed the food, just was hoping for a better overall experience."
    Dined on 2/5/2014
  • "Really unique courses - beautiful presentation. Everything tasted amazing!"
    Dined on 2/5/2014
  • "I was really excited to try this place out, and perhaps doing so outside of Restaurant Week would have been a better experience, but it turned out to be a total let down. Cute space, but the food was all pretty mediocre except for the dessert, and the service was really poor. We left the restaurant super bummed and salty about what felt like a large waste of money."
    Dined on 1/31/2014
  • "beautiful space, great food, knowledgeable servers. The only slightly negative thing we experienced was when my friend ordered the sweet breads as her main course from the Restaurant Week menu, it was very small and not really "entree size" at all. I completely recommend this place overall, though. The food runners were awesome about explaining what everything was as it came out, and everything we had was delicious."
    Dined on 1/31/2014
  • "This place is a total gem! The service was wonderful and the atmosphere was so unique and cozy. Located on the rooftop of Roots Pizza- it's an entirely unique environment of its own. The food was simply delicious. This was a slam dunk for restaurant week. There were four of us so we were able to try everything on the menu. Each plate was enjoyed!! Highly recommend this place! Great for a group!"
    Dined on 1/28/2014
  • "We went during Restaurant Week, & it was a very good experience. Service was prompt & pleasant; special requests were not an issue. Each course was delightful -- cocktails, too. Sitting next to the window, there was a bit of a draft. The style is conflicted between rustic & contemporary, & some interior finish choices seemed out of place."
    Dined on 1/25/2014
  • "I must say that they never fail to amaze me here. Brought a group of friends in for dinner, it was a good friend of mine, her birthday. Service was excellent. Food was beyond compare. Needless to say everyone was impressed to the very end."
    Dined on 1/24/2014
  • "You can tell a lot of effort is put into the food. If only the service was better. Everything was interesting, tons of texture. My taste buds were happy!"
    Dined on 1/24/2014
  • "We took my in-laws here for dinner, and everyone loved it. We've been to Homestead several times now, and we've always left very pleased. The food is fantastic, but make sure you also have one of their original cocktails because they're very unique and probably unlike anything you've had before. Also, make sure you save room for dessert - the vanilla roasted beets with dark chocolate and beet butternut sherbet was to die for. We ordered lots of different things and then shared them all, which worked out well."
    Dined on 1/10/2014
  • "In a word a fabulous experience. Dining mid-winter in the dining room still provided an experience of fine dining using fresh seasonal ingredients in unique flavorful ways. The ambience is comfy cozy and the service warm & friendly. The experience began with trying a two of the house created cocktails & a wonderful vanilla porter. Our trio shared the kale salad that was a great blend of flavors & texture. We ordered the three different entrees to share. The Walleye was amazing with a delicious crispy skin. Duck three ways was a true trifecta. Dessert.......OMG! A true Gem."
    Dined on 1/16/2014
  • "Food was very good, and the service was impeccable. They really encouraged sharing plates, which ended up being incredible. My sister-in-law has been in the summer, and says the outdoor space is amazing. Regardless, the indoor space was cozy and charming. Will return soon."
    Dined on 1/10/2014
  • "The dinner was delicious! We had the duck two ways, the duck egg and the walleye. So amazing. Their cocktail selection is delicious as well and they have great service."
    Dined on 1/10/2014
  • "I am a regular at Homestead. The manager Kate is outstanding. The chef always accommodates my vegan appetite while my friends and family consistently find a variety of meals To satisfy them. The setting is special and hard to find, on top of west town bakery and roots pizza but well worth it. You enter through Roots --then just ask how to enter Homestead There is a stairwell in the back of the restaurant to Climb to the roof top. The new intimate indoor swinger seating is wonderful but the true fun is the weather permitting roof top. I hesitate to give this outstanding review because it's a great intimate find but I want to share the word about the food, service and accommodations. Thanks Kate for always remembering my special diet!"
    Dined on 1/9/2014
  • "Charming rustic decor in a neighborhood full of character, this farm-to-table restaurant has imaginative food with a menu that changes with the seasons. Our party of 10 ate inside but the outdoor rooftop dining area is where we will sit in our next visit with a smaller group. The garden area that surrounds the outdoor tables is so atmospheric. We loved our food. The kale salad was one of the best I had. The cook pays attention to details like the sauces and salad dressings. The desserts were cleverly presented and memorable. The service was attentive without being overbearing. Next time I am in Chicago, I will be dining at Homestead."
    Dined on 10/12/2013
  • "I've been dying to try this place this winter. Sad that its to cold out to sit on the patio/roof, but inside was just as nice. The atmosphere is a perfect mix of romantic and vibrant. I took a date here and it was a perfect place for us to have a conversation, yet enjoy the night. The best part of this place is the food. We tried a lot of things and were not disappointed on any of them (rare for my date). My favorite was the Duck Egg Salad, and the Beef Short Rib Sugo. Her's was the Duck Egg Carbonara. Be sure to save room for dessert too... heaven. I am not a foodie, but do enjoy a good meal, and this place nails it. The service is perfect and craft cocktails were great."
    Dined on 1/4/2014
  • "New taste adventures await. Kind staff and warm surroundings."
    Dined on 12/31/2013
  • "We came across Homestead online and were enchanted by the photos---the kale salad specifically (I think it says a lot about a restaurant if they can seduce you with kale). We made some early selections ourselves, which were great, but asked Kate, our server, to recommend the entrees. All together, a really wonderful meal. We will definitely be back."
    Dined on 12/27/2013
  • "We enjoyed such a nice meal here. Incredible wine and food service (from Kate)...amazing "Wolf of the sea" with exceptional presentation; the braised short rib with parpadelle was exquisite; crispy chicken skins--yum! We enjoyed a north coast pinot that complemented all of our dishes beautifully. I am coming back and bringing friends."
    Dined on 12/18/2013
  • "Everything about this place is enjoyable. The service is awesome! The wait staff was very attentive and helpful, with great recommendations and very professional yet friendly presentations of each plate. They somehow managed to create the atmosphere of an actual Homestead but with an extra touch of class: It somehow feels very comfortable and homey but also exclusive and romantic. The food itself was spectacular: Every dish, every morsel and every cocktail was wonderfully crafted. Kudos on the awesome palate! Unfortunately because it's Winter, we could not enjoy the patio area but the view looked great and I'll be back come spring to get the whole experience."
    Dined on 12/15/2013
  • "Had an enjoyable experience. The server Emily was very knowledgeable about the menu and drinks. Everything form the menu presentation to good presentation/delivery was perfect. Great restaurant! Look forward to coming back when the outdoor space is open!"
    Dined on 12/6/2013
  • "My friend and I came here for a girls night, and could not have loved it more. Our server was so friendly and helpful, even providing tastes of some of the wines we had asked about. We split the farik, the duck egg salad, the short rib and the steak, and every dish was amazing. It was overall one of the best start-to-finish meals I have had in Chicago. Everything was fresh and perfectly cooked. I'll come back for sure."
    Dined on 11/23/2013
  • "We arrived for our 8:30 reservation, were deposited at the bar, ignored by the bartender for the first 15 minutes. Sans drinks, taken to our table that wasn't set-up. Waited another 10 minutes before we were visited by a server. (We were 2 minutes from just eating pizza downstairs.) Server arrived with no acknowledgement that we had been waiting. Put in drinks. First course arrived before they did. Husband's manhattan was warm, straight-up bourbon. Highlight of the night was the well executed Loup de Mer. Server made a quasi apology that we hadn't been able to receive her "normal level of love and attention" after dropping dessert menus, which we passed on. Maybe an off night, but we won't go back. Many other places with better service."
    Dined on 11/9/2013
  • "Tasty and leisurely meal at Homestead on the Roof. We were the first party in on Saturday night and we're never rushed through our meal eight plates plus dessert. Our server was very knowledgable about the plates and wine. Too bad it was too windy to sit outside after dinner."
    Dined on 11/9/2013
  • "Our server Kate was great and really made the experience even better. She made great recommendations and the food was excellent. The cocktail drinks were also very good and the atmosphere was warm and inviting."
    Dined on 11/6/2013
  • "Great Food. I love this roof top location. They growth their own produce on the roof and use it in their dishes. Very creative, knowelgeable wait staff. I want to go back in the summer."
    Dined on 11/1/2013
  • "We (my partner and I) came in for my birthday. We were greeted by the very lovely Kate. She gave us the low down on how things worked. We were hooked, we went mostly with her recommendations, the wine that she paired with what I was eating was sublime. We may not have had dessert, but there is always next time. We will be back, also I would like to say that Chef Chris Curren is on top of his game."
    Dined on 10/30/2013