Elevated Dining at Homestead on the Roof

“Are you sure we’re in the right place?”

A solid question from my lovely wife as we tried to make our way to dinner. We were invited out to try Homestead on the Roof, a farm-to-table dining experience where almost everything eaten is grown in house on their rooftop garden.

This is what they say about their spot:

Welcome. Homestead On The Roof— our cozy rooftop restaurant— is tucked away above Roots Handmade Pizza in the heart of West Town & features farm-fresh seasonal fare from Executive Chef Scott Shulman. The magic of Homestead is its 85-seat outdoor rooftop patio with full view of the L-shaped, 3,000 square foot organic rooftop garden, two massive, vertical hanging gardens, dozens of planter boxes full of fruits, veggies and herbs, and a fireplace.

Homestead was named a “Top 100 Fit for Foodies Restaurants in America” by OpenTable, named one of the “10 Best New American Restaurants In Chicago” by OpenTable, and has been named one of the best rooftop/outdoor restaurants in Chicago by multiple media outlets.

Sounds fantastic. And yet, here we we’re, standing in the middle of a sports bar pizza joint:

Say what?

Not that we would have minded watching the game, we were just a bit confused about the location. The GPS said it was correct though, as did the address on the door, and so we asked a server for Homestead on the Roof. She pointed here:

Ooooook. But sure enough, as we turned the corner and walked up to the stairs, we did get a sign in the right direction:

Which of course lead up to the creepiest murder-door or all time:

And out onto:


It really was a beautiful spot, perfect for a warm spring into summer night. We saw friends, dates, co-workers, everyone sitting together for a lovely dinner.


As mentioned above, the food is a beautiful collection of farm-to-table plates. We had a special tasting menu that evening but everything was seriously delicious. Here is what we ate:


Homestead Bread Basket

Fresh Baked Breads – Herb Oil – Honey Butter – House Pickled Cauliflower

5 Way Beets

Parfait – Nichols Farm Beets, Spiced Pistachio, and Goat Cheese

Tomato Sushi – Chrysanthemum Pesto – Salad of assorted ‘Tomatoes’

“Italian Beef” Tartare

Filet – Cured Duck Yolk – Roasted Cherry Pepper – Jus Gelee


Pork Chop and Pie

14oz Chop with a savory pie of rhubarb, bacon, and sausage

Hokkaido Scallops

Ragout of Cipollini, English Peas, and Lap Cheong – Fried Potato

Mashed Potatoes

Choice of: Classic, Roasted Garlic, Brown Butter, Miso, Black

Half Cauliflower

Slow Roasted Cauliflower – Mint Pesto – Cherries – Pomegranate

Coal Charred Asparagus

Fried Hollandaise – Togarashi

Basque Style Mushrooms

Hen of the Woods – Duxelle – Crouton – Hen Egg



Oat Dough – 41% Milk Chocolate Ganache – Torched Marshmallow



Ron Zacapa Rum, Honey, Lime, Sparkling Wine


Vodka, Cucumber, Prickly Pear, Mint

There we’re some standout dishes for sure. The scallops we’re perfectly cooked and filled with flavor. And oh dear god, that cauliflower with the cherries we’re amazing, better than most spots in this city who keep trying to do cauliflower but do it badly.

A few of the dishes we’re way way way too salty (like the tartar, which was sadly hard to eat it was so over-salted) but it was a small complaint for such an incredible meal.

Finally, those were perfect warm evening drinks. Sweet but not too sweet and all kinds of refreshing. I can’t recommend both enough.


Everything here is top notch. You are constantly looked after, the dishes come out when they’re ready so you always seem to have delicious food coming to your table, and the presentation as you saw above cannot be beat.

To match this, though, is of course the price. This is NOT a cheap meal. Starters come in at about $10 a dish and mains are about $30. However, for quality, constancy and just overall taste, you are getting what you pay for.

This may be a tad bit hard to find, but it is obviously worth the journey. If you’ve made it through the sports bar and up the stairs, I promise you, you’re in the right place for a truly amazing meal.