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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 WinnerOutdoor Dining
Diner Reviews
  • "Excellent job of making my family feel welcome. Food was so good and the presentation was fantastic by the waitstaff. We never had to wait for anything. Perfect in our book. We will be back with friends."
    Dined on 8/24/2014
  • "Overall, this was an wonderful experience from the food to the view. Everything that was served was not only tasty but very artfully presented."
    Dined on 8/22/2014
  • "I have been coming to Homestead since they opened and it really just keeps getting better and better. The service has always been fabulous - friendly, knowledgable, attentive staff (especially David)! The ambience is great inside and on their beautiful rooftop with low lighting and vintage pieces all around. And the food...amazing! It's always fresh, creative, and delicious. Not to mention the yummy drinks. I'm so glad this restaurant is in my neighborhood! :)"
    Dined on 8/22/2014
  • "I went to Homestead on the 16th of August to celebrate my 30th birthday with a group of 7 of my closest friends, at the end of a whole day of celebrating my favorite things. Homestead was an awesome way to round out the evening. We ordered nearly the entire menu and enjoyed every dish, especially the bread, salads, chicken skins, mussels, pappardelle, tagliatelle, and all the large plate dishes we ordered. Thank you for the dessert, it was a lovely way to end the meal! The service was great; we were able to order easily, order and re-order cocktails at just the right time, the meal was coursed out for us, plates were changed when needed, everyone was very attentive. I'll be returning before summer ends :-)"
    Dined on 8/16/2014
  • "We had a fantastic meal at Homestead. Everything was delicious"
    Dined on 8/15/2014
  • "The flavors are so fresh and the service impeccable. A rare find!"
    Dined on 8/13/2014
  • "The food was tasty! The server was a little intense seeming almost angry that we didn't want to order everything on menu. Small plates but good flavor!"
    Dined on 8/12/2014
  • "We didn't stay to eat at Homestead on the roof. We made a reservation, but they were so busy, they couldn't attend to us at all. We were told we couldn't be seated on the patio, which was disappointing, then put at a not very nice table inside. I asked a server/bartender who brought us menus whether we might be able to move to the patio later on (which I'd already asked the host and not been given an answer), and after she said she would go check, we were ignored for 20 minutes. We left, knowing that the experience world not get any better. For prices as crazy high as they were, I could not believe this was the level of service at Homestead."
    Dined on 8/9/2014
  • "Sweet Corn Agnolotti can't be missed. Share plates so you can try as much as possible."
    Dined on 8/9/2014
  • "Such a lovely surprise. Amazing atmosphere, delicious food and fantastic service. We came here on our anniversary and had such a wonderful time. For a rooftop restaurant it still feels like an intimate, fine dining experience, with some of that rustic farm to table flare."
    Dined on 8/6/2014
  • "Part of the draw is the outdoor seating along with the good food. We had some friends in from out of town and made reservations. We arrived for our reservation on time only to be told that it would be 60 to 90 minutes for outdoor seating. Had we been told this when making the reservation, we may have made reservations somewhere else or at least been aware that we may not be seated outside, but in the small dining room instead. It is quite disappointing to find out that you options are dining room or wait 90 minutes when you arrive at a place that touts rooftop dining. This lead to a blah experience."
    Dined on 8/2/2014
  • "All four of us in our party had delicious food. All members of the staff made fantastic recommendations for the food and understood what went well together so we could all share and get a taste of everything. The design of the outdoor seating area was perfect - you felt like you were in a hidden garden party with the garden so close and the strings of lights. Highly recommend!"
    Dined on 8/2/2014
  • "The service from extremely knowledgeable servers (David!) makes for a pleasant dining experience. The drink concoctions are brilliant, as is pretty much the whole menu. We came here with an open mind to try different combinations and were not disappointed. If I had to pick out an improvement, I would say the portions need to be a little bit larger to match the prices. I would stop telling diners that the plates are shareable. The portions are a little too small for that, but fine for an individual serving."
    Dined on 8/2/2014
  • "One of the best dining experiences I've had in Chicago! Fresh local food, great drinks, dessert and atmosphere. My boyfriend and I have been raving about our experience!!"
    Dined on 8/1/2014
  • "Roof top setting very unique, great summer evening spot; delicious food, great opportunity to eat family style and share dishes; service was a bit slow a times, particularly refilling drinks/wine;"
    Dined on 8/1/2014
  • "I took my boyfriend here for his birthday and we had an amazing time. I made reservations for a Friday at 7pm - we were able to eat out in the garden no problem. We ordered three dishes to share, the pork belly small plate, and the duck two ways and the half chicken large plates. For two people this was more than enough food and we were hardly able to finish our last plate. All of our dishes were exceptional, although I will say that the half chicken was my favorite of the three. The only slight downside to our evening was that because the cocktails are all handmade, sometimes the bar gets backed up and it takes what seems like a while to receive your drink order - definitely worth the wait though! Overall I would definitely recommend!"
    Dined on 8/1/2014
  • "Thoroughly enjoyed the rooftop treasure. Seeing the vegetables growing was delightful. Food was VERY fresh, interesting and complex. Couldn't eat that way every night but certainly enjoyed the experience."
    Dined on 8/1/2014
  • "This roof top spot is super cool, and the drinks were wonderful. We were disappointed in the food. My duck was way to salty."
    Dined on 8/1/2014
  • "ease up on the wine prices! Most foodies love a glass (or 2...) of wine with their food. But the cheapest glass of wine at Homestead is $11! Some of us were drinking $14 glasses. That's the highest I've ever paid in the city of Chicago or anywhere for that matter. Plus, it's a short glass of wine. I think if the drink list was improved, this place would be topnotch. The food is wonderful and easy to share. It's a wonderful experience on the rooftop, surrounded by green, a garden, and a thoughtful atmosphere. The staff was down to earth and friendly."
    Dined on 7/31/2014
  • "One of my favorite restaurants in Chicago. Have been 3 times and it has not disappointed yet. Food is phenomenal--adventurous but not overly 'experimental', and most of the produce is grown right in the garden. Servers are great--knowledgeable but not pretentious, and fun. Drinks really stand out, which is difficult in this city's vibrant cocktail scene. Each time I have gone, the rooftop was packed (or closed when it was winter) but the interior had availability. It's a really nice atmosphere inside, so"
    Dined on 7/26/2014
  • "Homestead has become one of my favorites places in Wicker Park / West Town. Creative dishes that are perfectly executed, you have a hard time choosing which one you like best. Service is fantastic and they are able to match the tastes of the table with specific menu items. Can go wrong ordering a few plates and sharing with table to get a little bit of everything. Keep it up!"
    Dined on 7/25/2014
  • "Every course was wildly different. Favorites were mussels, corn agnolotti, and rice balls. Very fresh, unique flavor blending. Bar drinks were a little stiff. Highly reccomend for something unusual and tasty."
    Dined on 7/25/2014
  • "Loved the dinner here. Wanted to lick the plate with many of the sauces. Did not like our desserts. Atmosphere was pretty, rustic."
    Dined on 7/23/2014
  • "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