About Homestead On The Roof

Homestead On The Roof, located at 1924 W Chicago Ave, Chicago, IL, is a vibrant Portuguese restaurant that’s become a local favorite. Its laid-back atmosphere invites diners to enjoy a taste of Portugal in the heart of Chicago, offering a cozy spot for a night out or a casual meal with friends. Whether you're in the mood to relax with a glass of wine or indulge in a comforting plate of food, this restaurant has something for everyone.

One of the standout features of Homestead On The Roof is its versatile service options. With outdoor seating available, you can enjoy the fresh air while sipping on a cocktail or beer. If you're in a rush or prefer to eat at home, takeaway is also on the menu. For those who want the full experience, the dine-in service allows you to savor each bite of their delicious offerings in a relaxed, welcoming setting.

The menu is a blend of Portuguese flavors, featuring comfort food and small plates perfect for sharing. Whether you're craving late-night food, a light snack, or something more substantial, Homestead On The Roof has you covered. From hearty vegetarian options to flavorful spirits and cocktails, there’s something to please every palate. They even have a private dining room for special occasions, making it an ideal place for intimate gatherings or celebrations.

The drink menu is just as impressive, offering a variety of alcohol, beer, wine, and cocktails, alongside rich coffee to wrap up your meal. Whether you’re there to enjoy a laid-back drink with friends or looking for a full-course experience, this place has everything you need to unwind and enjoy the best of Portuguese cuisine in a chic, rooftop setting.

Special Menu

Roasted Broccolini

................................US$15.00

Saffron Cream, Candied Almonds

Elote

................................US$8.00

Garlic Lime Aioli, Cotija Cheese, Paprika Breadcrumbs

Duck Rice

................................US$14.00

Duck Confit, Apricots, Herbs, Fried Egg

Confit Potatoes

................................US$12.00

Saison, Lemon, Fried Red Pepper

Pambazo

................................US$22.00

Talera Bread, Guajillo Salsa, Roasted Potatoes, Poblano Peppers, Shredded Lettuce, Queso Fresco

Portuguese Steak Sandwich

................................US$28.00

Papo Seco Bread, Shallots, Garlic, Portuguese Peppers, Fried Egg, Served with Fries

Cod

................................US$22.00

Saffron Cream, Tomato and Onion Relish

Scallop

................................US$22.00

Celery Root Puree, Nduja, Escabeche

Full Menu

Gallery

Business Info

Service options

+ Outdoor seating

+ Takeaway

+ Dine-in

Highlights

+ Great cocktails

+ Great wine list

+ Rooftop seating

Popular for

+ Dinner

Accessibility

+ Wheelchair-accessible entrance

Offerings

+ Alcohol

+ Beer

+ Cocktails

+ Coffee

+ Comfort food

+ Late-night food

+ Private dining room

+ Small plates

+ Spirits

+ Vegetarian options

+ Wine

Dining options

+ Brunch

+ Dinner

+ Catering

+ Dessert

+ Seating

+ Table service

Amenities

+ Bar on site

+ Toilet

+ Wi-Fi

Atmosphere

+ Cosy

+ Romantic

+ Trendy

+ Upmarket

Crowd

+ Family friendly

+ Groups

+ LGBTQ+ friendly

Planning

+ Dinner reservations recommended

+ Accepts reservations

Payments

+ Credit cards

+ Debit cards

+ NFC mobile payments

+ Credit cards

Children

+ Kids' menu

1924 W Chicago Ave, Chicago, IL 60622, United States

Reviews

We had our October wedding at Homestead and it was truly magical. Sam our venue coordinator was above professional - she reassured us in the last few weeks before our event and kept things running absolutely perfectly on the day of. Every member of the staff crushed and our guests raved about the food and service. Beautiful space, beautiful food, beautiful day.

- Mariel Tish -

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 -

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 -

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 -

Homestead on the roof is amazing. I appreciate the staffs and managers kindness to me even though I have autism and their food is amazing and really good. Owner Scott is very nice. The restaurant is in good condition. Amazing pork confit. Must come back. 10/10.

- Curtis Park -