Homestead On The Roof

It was good and the place was so cute but it really didn’t blow me away. We came during the winter so the patio was not open, which I know is a main draw of this place!
The design and décor of the inside was so cute. It’s very organic feeling with lots of indoor plants and wooden tables/​chairs/​exposed beams, etc. The service was excellent. It wasn’t busy (only 1 – 2 other tables in the whole restaurant), so there was only 1 server working, but he was attentive to all of his tables.
Their menu and dishes changes frequently, so I would definitely be up for trying this again in the future. When we went though, we ordered the Bread Basket, Pig’s Foot, Pappardelle and the Curried Mussels.
Bread Basket: Great assortment of homemade breads & rolls, which is a great way to start off any meal! The bread was fresh and delicious and served with an assortment of condiments/​spreads.
Pappardelle: Very rich and had good flavors, but it was almost too rich.
Mussels: Cooked perfectly and served in this creamy curry sauce and extra bread to soak up the sauce!
The food and service were good, but nothing on the menu really blew me away!
I’d consider coming back to try out the summer ambience & meals definitely!

Interesting and good food selection. I want to go back when the gardens are producing fresh produce. Steak, halibut and chicken were all great. Our server Daniel made the night enjoyable.

Really wanted to love this place. Read a lot of excellent reviews. Homestead had great service, quality cocktails, and a beautiful ambiance on the roof. Why the 2 stars? The food was terrible — especially for the cost. We ordered the sweet breads, the cauliflower steak, the ribeye, and the arctic char. The food was bland, lacked seasoning, and not executed well. The Arctic char was so bad (dry and tasted poorly) that we had to send it back — and that is something that I never do. It takes a lot for me to even make a complaint. Our server was very accommodating and removed it from the bill. Maybe it was an off night in the kitchen, but with so many other options in the city, a repeat visit isn’t likely.

I had a bad experience on my last visit (which was my second time eating here)
1) We arrived on a Saturday night with a reservation but requested an outdoor space and were willing to wait for a table. The host said that a few tables were paying their tab and he would come find us at the bar when our table was ready. Forty minutes later I checked back with him and he acted as if we’d never spoken before (he asked if I had a reservation how big my party size was, if we wanted an indoor table). It was clear he forgot about us. Not ideal but it was a busy Saturday night so I’m sure he had a lot going on. So we were basically sat an hour after our reservation time
2) Our waiter was a super nice guy but slow and was clearly spending a lot of time on his cellphone which added to our wait. Our drinks arrived 25 minutes after we ordered them (we had finished our appetizers by the time they arrived) The second round of drinks took equally as long. We also had to wait 20 minutes for our bill to arrive after requesting it. The table next to us had a similar experience and scolded the waiter for it, so I don’t think we were the only table who felt this way. I tried flagging him down a few different times but was staying out of view in a corner texting
Having said all that, the food was good, it just took longer than expected. Also, I think it would have made the experience better if there was some sort of service recovery effort for forgetting about our table and the long waits for the drinks food and check). I kind of got the impression the host felt he was doing us a favor by seating us rather than being appreciative of our business and willingness to wait

Went to an anniversary dinner here — it was the perfect place! romantic ambiance and delicious food. Not good if you are on a budget, but it was a special occasion. We had the bread basket which was served with a herb infused oil and a spiced butter that was decadent. the salad we had included brussel sprouts, fish oil, fried corn bread, etc. it was so delicious. ¹⁰⁄₁₀ would recommend.

Went here a couple days ago and had one of the best dinners ever! We went around 6:30 on Friday to beat the crowd, and thankfully we did! Four of us shared everything so that we could each try all of the dishes. We started with chicken skins, the bread basket and smoked whitefish. It was all amazing! I’m not a big fish fan, but the smoked whitefish was actually light and delicious, and a bit refreshing with the pickled veggies that came alongside it. We then shared the ribeye, the halibut and the cauliflower steak; who knew that cauliflower could be so tasty?! We also saved room for dessert, since they have a james beard nominated pastry chef. Boy, did web hit the jackpot! We shared the strawberry shortcake and butterscotch. Will definitely be coming back in the summer once the patio is open

One of the most hidden gems in the city of Chicago!
Not only is each visit unique with regards to the food selections, but the staff is incredible friendly, attentive, and knowledgeable. Each dish is almost like a hand crafted piece of art that is as delicious as it looks. The chefs are absolutely brilliant at combining ingredients to make the most tasteful dishes I have ever had.
The décor is beautiful as well! A restorative hardware look that compliments the city landscape! I was hesitant to write this review because I love how hidden this place is but it’s too great not to share!
If you’re looking for a unique gem with some of the most unique and tasty dishes in the city, you need to give homestead a try!

We came here for drinks and dessert. The entrance is actually through the bar downstairs and restaurant is upstairs. It’s upscale rustic vibe to the menu and space. The 3 cocktails we tried were all good. the pineapple dessert was more tart and the beignets (more like donuts) were not a let down. I certainly liked their dessert amuse bouse at the end… they had quite the collection of assorted sweets to pick from.

Homestead feels like a spacious winter cabin, but with gourmet, locally sourced meals.
The bread basket is a must — suffice your carb cravings with 3 kinds of breads and accouterments you’ll have to consume separately because the breads are fantastic on their own.
«Medium» sized orecchiette is a normally-​sized entrée full of delicious flavors (maitake mushrooms, shaved beets, turnips, smoked goat cheese) & «large» size grilled lamb entrée is truly large. Indulge in 3 lamb chops, merguez sausage, & preserved eggplant on a bed of savory local grits.
Great seasonal drinks and a surprise dessert, so save room (or don’t — you’ll eat it anyway!).
If all that wasn’t enough, they’re featured in the Giftie app!

Once upon a time, a few years ago, I had my first date here with my husband. Now, we live a few blocks away from Homestead. We haven’t been back until my husband planned our Valentine’s day dinner here last night. The night before, he got a phone call saying that the regular menu was not going to be available, and that there was a pre-​fixe meal only. Kind of a bummer, as there was a dish on the regular menu he really wanted to try. Regardless, we went with the pre-​fixe menu (not that we had a choice), and it was wonderful! There were 5 courses, and an optional wine pairing for an extra $ 25 each — of course we got that too.
Before our meal, they gave us a complimentary shooter, which tasted like a really good soup. I think the waiter said it had maple bourbon in it?
1^st course — I got the chocolate covered foie gras, husband got the Kushi Oyster. I don’t typically like foie gras or oysters, so this was probably my least favorite part of the menu. The chocolate covered foie gras looked like a piece of candy, and when biting into it, the foie gras was like butta. It was good, but I only ate half until I couldn’t take the texture/​flavor anymore.
2^nd course — We both got the chicken fried ½ quail. So good! I loved the asian flavors of this.
3^rd course — We both got the seared scallop. It came with one large scallop, a mini scallop, a little foie gras, and 3 mussels. The scallops were perfectly cooked and the sauces and foie gras were the perfect complement.
4^th course — We both got the lobster. This was the BEST dish of the night! The lobster with the uni broth was heaven! I was so full already but was determined to finish this dish.
After this course, we got a complimentary pre-​dessert of chocolate mousse and frozen beets. I was scared to eat it, but it turned out tasty!
5^th course — I had the dessert that had a combination of chocolate and passion fruit. Really good combo!
Then, we got some complimentary chocolates! I couldn’t even try these because I was so full from the food and wine, so I took them home.
Must come back for their regular menu! It was an amazing Valentine’s day dinner! Our server gave me a long stem rose, the managing partner came to make sure our dinner was going well, and the ambiance was perfect.

Beautiful ambiance once you get to it. Not the most convenient local but nonetheless a rather unique use of space. The lodge style setting is very relaxed and akin to an old farm house. Bell jars of pickled items adorn walls of antiquated wall paper and vintage lamps. The menu read rather nicely however some of the execution was lacking. I feel there is room for improvement so I’m willing to give it another try in time. Perhaps they’ll dial in the kitchen a bit.

It’s long overdue, but I owe Homestead a review. Homestead is one our favorite date night spots. Great wine, tremendous sensible food, and the best dessert! Service is always on point — from our always friendly servers to the food runners that intricately explains the food. Lots of hard work and training was put in.
We’ve been here at least 20 times over the years. Just like fine wine, they have gotten better over time. You guys deserve a Michelin star. I’ve been to many starred places, and so many aren’t even sniffing your level. Great job Homestead and keep up the amazing work!

Meat. It should be cooked. I know. Fashionable meat lovers seem to like everything rare. And overcooking lamb is awful. But when someone orders their hanger steak to be cooked medium… It should not be shiny translucent pink on the inside. And one should be able to get the lamb meat off the bone.
It’s pretty there, but it’s expensive and the food was mediocre. Oh well.

Went there with a party if 8 the other night and the food was excellent. I’m gluten free and they were very accommodating! I shared food with people and they even said the gluten free food was very good. We left there super stuffed because everything was so good. So why 4 stars instead of 5? The service was just okay. Our dinner reservation was for 7 and we left there at 10:15 and it was not because we stayed to talk. It took 45 minutes to order and then 2 hours for the food to come, that’s crazy!!!
Overall, I thought the waitstaff was nice and accommodating. The bus boys took long time to clear plates and the food between each course took forever to come out. We will absolutely return because the food was so good but just plan for sitting there a long time.

The rooftop is definitely their forte. It’s rustic yet urban at the same time, and they grow a lot of their ingredients in a large, long plot. There’s also what looks like a retractable roof to shelter from rain, but they didn’t use it when it actually started raining; instead, everybody ran inside mid-​meal and waited to be seated at a table, and it was hot & humid in there. Luckily, we didn’t have to wait too long, but there was a weird 15 minute hiatus in the middle of our meal because of this.
Food was average to good but not amazing. The Violet cava cocktail really photographs well and isn’t too sweet. The papperdelle and the scallops with foie gras were my favorite dishes. Some of us thought the hangar steak was too salty. I can’t really remember the rest. After sharing a bunch of dishes and 1 cocktail pp, we were each $ 40 poorer and still a little hungry and contemplated going downstairs to Roots to pig out on some comfort food…

Less creative than before, less interesting, less delicious, and worse service. Good veggies.
Annual summer visit to Homestead.
Ordered lots of dishes.
Bread: ⁵⁄₅
Mussels: ²⁄₅
Gem salad: ⁴⁄₅
Suckling pig felafel: ²⁄₅
Pasta with mushrooms for my son: ³⁄₅. Very small portion as a main dish.
some other kinda pasta, a bit arabesque: ²⁄₅
Walleye: ⁴⁄₅
Side dish of veggies: ⁴⁄₅
Cherry desert: bad. overly sweet.
Huckleberry desert: awful. talk about hiding shit under sugar.
Drinks: 3 cocktails. Bad for the most part.
Service: Took forever to replace two dirty knives. Guys check your stuff before putting them on the table.
Very slow. I like not getting rushed but i do not like inattentive service. A few times felt i was waiting forever for the server to come.
They used to have some veggie side dishes before but this time nothing. Kind enough though to do one for me.
I was probably a bit too nice in my prior reviews. Even though they are more of a 2.5 than 2, this time i give them a 2. After all these years i’d hope they get better.
I will go back though but eat less and focus on the veggies.

Every time I’m in town, I’m sure to eat at Homestead on the Roof. I love their seasonal, fresh farm-​style menu. The service is always friendly and attentive and the food is consistently phenomenal. It’s a great place to dine with friends. They have a great wine and cocktail menu and the atmosphere is casual yet refined.

If you are looking for change of atmosphere, I was very impressed with their outdoor space. It is a very trendy rooftop garden with a casual chic feel to it. The service is very friendly although the waiters rotate so if you like to build rapport with your server, thats not going to happen. However the girls and boys in plead and skinny jeans are very attentive!
The dishes are all very interesting, (everything comes out served in casual pottery plates in muted colors) and presentation is outstanding beautiful and unique. However while our appetizers (oxtail croquettes and pea pasta course) and dessert (cherry panna cotta) were outstanding, both our main courses sounded and looked way better than they tasted. We had Venison and Steak. Venison was served with lentils, had great flavors, but was very tough and chewy. About the Steak… let’s just say I am glad my husband was willing to eat it. He is a tolerant and patient man :)
Wine list was also disappointing, very few by the class options (almost all the white choices were from Italy). They were out of one of the few reds… It seems like the place doesn’t care about wine:(

Came here during Chef’s Week (four course prix fixe meal for $ 40), and our overall experience was really really good. When you get to restaurant, you walk through their ground floor pizza establishment (Roots) towards the bathrooms/​stairwell. From there a hostess will escort you upstairs Homestead. Their rooftop wasn’t open for the season yet (it looked really cute though) but their interior dining area was really nice — rustic and quiet and relaxing.
We selected items from the prix fixe menu and both decided to do the wine pairings that accompanied the meal. I decided on the beet salad, prawns, lobster, and the black pepper beignets with ricotta. They brought a bunch of homemade breads out with our salads — along with some pickled beets (delish!!!), honey butter, and some green super garlicky oil based mixture that was like crack on the breads they provided.
The highlight of the meal (for me at least) was the lobster course — a large lobster tail over a root vegetable mash (maybe potato? I don’t quite remember now) with a amazing uni bisque-​like sauce. Rich and absolutely delicious. There was a weird gap where they gave me my dish, but didn’t have the sauce ready, so I sat for a while with a half presented dish — maybe four or five minutes. But once the dish was sauced, it was marvelous.
Will definitely be back to check out their rooftop now that (I believe) it’s open.

Homestead sort of feels like one of those «in the know» Chicago spots… kind of like those basement bars within a bar (i.e., The Library at Gilt, The Office at Aviary), only the kinda opposite since it’s a rooftop restaurant within a restaurant. Homestead is the older, sophisticated sibling to Roots Pizza, nestled atop. You enter through Roots, weave your way past the beer taps, awesome-​sauce pizza, and screens tuned to ESPN and the like in order to reach the hostess stand and work your way up a staircase to Homestead.
The rooftop patio opens in May, and exterior seating in perfect Chicago summer weather likely adds an additional star to any review. As it were, we went in April and had access only to the very homely, stately kitchenette indoors. The menu is farm-​to-​table, with a nice emphasis on garden-​procured goodies. The bar is also well-​manicured, and I went with an Old Fashioned that was heavy on the muddled sugar but otherwise fine.
The two dishes I liked most on the night were the black rice truffled grits and the fazzoletti. Like Bourdain, I disdain truffle oil but for different reasons, simply because I don’t generally prefer the smell. The truffleness was hardly present in this dish, masked within the buttermilk sauce draping the side. The dish was elevated when all bit in tandem with the very crispy, very delicious lamb bacon and a slice of the perfectly cooked sunny-​side duck egg.
The fazzoletti was the last dish served on the night, which is a shame because we were completely stuffed. The pasta was lightly layered and partnered well with a crispy shaved carrots. Flavor-​wise, I really loved the lemon-​ricotta pairing as the sauce base.
The six dollar bread basket gets lots of kudos as well, and I don’t disagree. Ours came with cornbread and a serrano ham pinwheel, both which were spectacular. The pickled beets are worthy of the entry fee alone, without mention of the honey butter and pesto dip.
Unfortunately, our other offerings ranged from average to mediocre. The dud of the night was the mackerel escabeche, which was flavorless and dry. I typically love grilled saba at Japanese restaurants, but this was disappointing, and the tasty squash purée in no way made up for the mediocre fish.
All in all, there were a couple hits and a couple misses, but a terrific atmosphere that could only be improved upon by al fresco seating. Homestead doesn’t seem to have gotten much pub on restaurant lists, which is a shame because it’s an interesting dining experience worthy of more support.