Homestead On The Roof

“Very nice atmosphere on the rooftop patio, and it was nice there’s not too much noise from Chicago Ave.”

Very nice atmosphere on the rooftop patio, and it was nice there’s not too much noise from Chicago Ave. all the dishes we got were great, but my favorites were the Muscles, Beer Braised Short Ribs, and the Confit Spicy Crispy Potatoes.

Claire Hess

Aug 2024

“Such a lovely spot tucked up and away, perfect for a cooler summer evening like today.”

Such a lovely spot tucked up and away, perfect for a cooler summer evening like today! Our server Adam was very kind and knowledgeable. A great taste of Portuguese cuisine!

Kelsey Hodgson

Jun 2024

“Amazing!! This place was such a lovely and charming garden rooftop. It’s tucked away above Roots...”

Amazing!! This place was such a lovely and charming garden rooftop. It’s tucked away above Roots Pizza, giving it almost an exclusive vibe. Good for any occasion - dates, friend groups, business groups, etc. The food was amazing and yummy!! We loved every single dish and drink. Don’t overlook this place when nabbing a dinner reservation. I would put it up against many other nice “white table cloth” type restaurants, in the city.

Michelli Rivera

Jun 2024

“Despite the less than ideal weather for our mostly outside venue, Hilary & the team at Homestead...”

Despite the less than ideal weather for our mostly outside venue, Hilary & the team at Homestead went above and beyond to make sure that our wedding was absolutely perfect. Our guests raved about the food, the drinks were great (and quite strong), and the servers were all so kind. S/O to Lupe for being so, so wonderful (I thought so, and a couple of our guests mentioned how awesome she was as well).

Aria Gabrielle Frawley

Jun 2024

“As a Chicago wedding photographer, Homestead on the Roof is a venue that captivates me every time I shoot there.”

As a Chicago wedding photographer, Homestead on the Roof is a venue that captivates me every time I shoot there. Nestled atop a cozy rooftop garden, it offers a unique and intimate setting for weddings. The lush greenery and rustic charm create a picturesque backdrop for photos. The staff's attention to detail ensures that every moment is captured beautifully, making it a joy to photograph weddings at Homestead on the Roof.

Sarah Nader Photography

Feb 2024

“This is such a unique venue with INCREDIBLE food.”

This is such a unique venue with INCREDIBLE food! It's perfect for an intimate wedding in the heart of West Town. It was clear that guests truly enjoyed their experience and that everything was very organized and well-timed. 10/10!

Madi Ellis

Dec 2023

“We got married at Homestead on the Roof in June and are in AWE at how perfect this venue is.”

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 at Homestead!!

Megan Sullivan

Aug 2023

“We’ve made a tradition out of going to Homestead every summer, and this summer did not disappoint.”

We’ve made a tradition out of going to Homestead every summer, and this summer did not disappoint! I like things spicy, so I appreciated the spice levels of the pork belly and potatoes. My favorite dish out of our order was the scallops! I’m excited to come back next year for a whole different menu.

Andrea Pesola

Jul 2023

“Had the opportunity of dining at a beautiful hidden gem in wicker park.”

Had the opportunity of dining at a beautiful hidden gem in wicker park. Homestead on the roof definitely is a must. Service is not top tier but friendly. The food was so good! Legit everything we ordered we ate and loved. We started off with the croquettes, presentation super cute and flavor wise- so delicious. Medium plates we did go for the charred octopus and shishito peppers. The Octopus was barely charred definitely needed a bit more time on the grill as did the shishito peppers, however, as food techniques are important so is flavor and homestead definitely has a great palate. Entrees I had to have the scallops and my partner had the Roasted half chicken and we ordered the Duck rice as a side! SOOO GOOD. Scallops and chicken to die for but the duck rice?? SUPERB. Blew my mind how delicious and well balanced the flavors were. I mean apricots in a duck fried rice?? Definitely keeping that in mind for my home recipes!! I can’t remember our servers name, Mia maybe? We were the only table on the roof considering the weather had dropped. I’m honestly looking forward for my next visit!

Denise

Jun 2023

“Great experience.”

Great experience. My husband took me for our first year anniversary and everything was amazing since the beginning. Romantic vibes, the staff is super nice, food incredible amazing and the dessert was 🤩🤩🤩. Highly recommended.

Alison Miller

Aug 2022

“Romantic, great vibes, great fine dining…what more can you want.”

Romantic, great vibes, great fine dining…what more can you want. This rooftop blew me away considering this was my first time experience here. Homestead definitely is the spot. Food had great flavors and textures and the presentation was amazing. Will be visiting here again

The Duchess Reviews

Jul 2022

“Honestly, this is a GEM of a restaurant.”

Honestly, this is a GEM of a restaurant. The Filipino flavors were amazing and beautifully constructed. Every dish left me speechless. The service was amazing. Our water's were never left unfilled. The owner (I believe he was the owner) would always check on us and ask us how the food was! The pictures don't do it justice at ALL. We will be back for the brunch menu!!

Jessica Ogueri

May 2022