Homestead On The Roof — Restaurant in West Chicago Township

The restaurant is nicely designed, I did not see an elevator so that is problematic as the restaurant is atop of Roots Handmade Pizza in West Town. If there is an elevator that I missed, there's not a ramp that gives you access to the rooftop patio, which is unfortunate.

Our server recommended we share plates, so we opted for that. While they were very friendly and polite, we didn't get a detailed breakdown of dishes or recommendations until we asked them. The menu has a wide variety of vegetarian & gluten free options.

Cocktails: (menu on website is from Summer 2023, not what's at the restaurant) My friend said the Mixologia ($16) was fantastic. I am living sober, upon request, the bartender was kind enough to give me an alcohol-free variation of the Mula ($14) and it was so refreshing. However, the cocktails are pricey. I wish they would consider adding more spirit free cocktails to the menu instead of only having Portuguese soft drinks.

Food: I was incredibly disappointed to learn the menu had turned over for the season. The salmon that I had been dead set on trying was no longer an option. We started Pesticos with the Azores Tartine ($12): Chili Cured Egg Yolk, Herb Goat Cheese, Sourdough, Charred Scallions. I wish a thinner, softer bread had been used so that we could really observe the flavor on our tongues. I had to pick at the top in order to taste it.

Then we moved onto the Entradas, ordering the Rooftop Salad ($17): Heirloom Tomatoes, Blood Oranges, Mint, Shallots, Freeze Dried Satsumas, Orange Vinaigrette. This needed salt and ground pepper. If you love tomatoes, this is for you. It was light and somewhat refreshing but just ok.

Under Pratos (large plates), we ordered the Beer Braised Short Ribs ($33): Beer Braised Short Ribs, Garlic Mashed Potatoes, Caramelized Cipollini Onions, Pickled Red Onions. What's missing from the aforementioned description is the mushrooms. Color me disappointed to learn these ugly, tasteless creatures were sprinkled around the dish. The short ribs are sitting atop of the garlic mashed potatoes in a bowl. It's incredibly difficult to cut this way without making your dish look like dog food before you've taken your first bite. Additionally, there's all this wonderful juice in the bowl that we could not scoop up because the dish doesn't come with a spoon. The meat lacked any real flavor, a common theme echoed throughout each course. Now, the garlic mashed potatoes were perfection, which further irritated us that the meat was not. Very pricey dish to not be satisfied with. I definitely had a better version of this dish at other restaurants.

Total Bill: My friend had 3 drinks and I had two cocktails, that pushed our total to $127.30

Overall, I'd highly recommend Homestead on the Roof for rooftop patio drinks (no skyline views). It's a nice place to start for drinks. Unfortunately, this area of West Town isn't bustling with a ton of restaurants. If you're a fan of Roots Pizza, you can always start upstairs then work...

Will never be back. Read on to hear my experience.

Made a reservation 2 months in advance for my husband’s birthday; got a babysitter and was so excited to sit on the patio on a beautiful night.

When I checked in, the first host asked “do you have a reservation” when I said yes, she said “oh, well there’s a wait” (without looking at a list or anything). A second host walked over, same spiel, she told us that some tables arrived at 5 and were coming close to hitting the 2 hour time limit they impose so they would be leaving soon and recommended we get a drink at the bar to wait 10-15 minutes for our table. We gladly accepted.

The bar was crowded; we later learned every person sitting there was also waiting for their reserved table... we had to stand near the bar for a bit but ordered a cocktail each. After ~10 mins, the bartender told us she forgot our orders and asked us what we had again. Then she made them, we paid and we were content.

35 minutes later, we still weren’t seated or acknowledged. I checked in with the host again and she said a table was paying now but that she couldn’t guarantee that they would leave right away (she had no response when I asked about the 2 hour time limit she mentioned earlier).

45+ minutes after our reservation, we finally get seated. The server asks if we just got there, we say “no we’ve been here close to an hour now” he laughs and says “ok... so here’s about our menu”. He also wasn’t familiar with the portion sizes, asked if we were ready to order 5 mins after taking our order, and told us we had to wait on our last dish because they were out of large plates.

We never do this but we shared our frustrations with the manager. He doesn’t apologies but tells us we can stay as late as we want. We didn’t want to ruin anyone else’s experience by staying too long and we had a sitter at home to relieve so we quickly left after we ate.

Sadly, we did actually really like the food but the service was too terrible. Why bother taking reservations if the time...

We got married at Homestead on the Roof in June and are in AWE at how perfect this venue is. Jena was our event planner, her and her crew went above and beyond to make our day so seamless and unforgettable.

Jena and the events team had amazing communication, was accommodating to our requests, very organized and delivered all of our needs, and our chats were always fun and extremely informative. They really know how to host a wedding! We had 90 guests at our wedding and were worried it was going to be tight during the dinner portion, Jena really helped us with our seating chart to make sure everyone was comfortable without having to sacrifice our guest list.

The food and drinks were great and we received many compliments from our friends and family. Again, we loved the staff. We had guests who spent a lot of time at the bar (go figure) but really loved chatting with the bartenders.

I don’t even have words to describe the rooftop. The twinkly lights on the patio, the lush garden, the Ivy wall with planters!!! Ugh it was so dreamy! We have unreal pictures from our wedding in so many different spots around the venue. The indoor area is beautiful too. They provide a TON of little candles they lit so our dinner portion was just magical especially with our flowers.

If you are looking for a small/medium-sized wedding venue that has charm, great staff, intimate vibe, great food/drinks and service… DON’T HESITATE to check out Homestead on the Roof. This place will forever hold the most special place in our hearts and we cannot wait to keep going back and reminiscing on our special day.

THANK YOU Jena and everyone...