Homestead on the Roof

New American
$ $
1924 W Chicago Ave (at Winchester)
Chicago, IL 60622
5:00pm - 11:00pm
5:00pm - 11:00pm
5:00pm - 11:00pm
5:00pm - 11:00pm
5:00pm - 11:00pm



  • Besides boasting a rooftop that features tables made from reclaimed barn doors, the spot also has a menu with some pretty good eats. An all-Midwestern beer selection helps wash it all down.
  • The food was inventive but the baseball steak was really tough!! And our waitress sort of forgot our dessert so dinner took 2 and half hours!!!!!!!
  • The scallops, foie gras, and truffle potato were amazing. Beautiful presentation and high quality ingredients. This place is the real deal! HIGHLY recommended!
  • Sitting in the middle of a garden having dinner you forget you're in the city! Staff is super friendly and knowledgeable and the manager will go out of her way to make your experience extra special!
  • Pasta, lamb, chicken skins, rooftop
  • The bread basket is simply delicious and the duck is fantastic.
  • Reopened for the summer with beefed-up staff. New executive chef Chris Curren and beverage director Ben Schiller have the people talking about the food, cocktails, and rooftop garden.
  • Pork belly with squash fried chickpeas,squid ink pressed pasta with octopus,clam bake-an explosion of flavor, and fried pork tail. Amazing variety of flavors.
  • Try the: 'Two Way Potato', 'Crispy Vegetable Tempura', and 'Seared Scallops'. Nice West Town rooftop when it's not raining. Order drinks. Enough said.
  • Most excellent dining experience on opening night. 7 various shared dishes, 2 desserts, and a few drinks. Fresh food taken to a new level.
  • I loved the rooftop. We went for brunch, which is made/served by West Town Bakery. The food was just fine, but the ambience was unbeatable. Oh, and they know how to pour mimosas here :)
  • Located above Roots Pizza, it truly is a respite from the big-screen TVs and carb overloads to be had downstairs. The ever-changing menu always offers some unexpected pleasures.
  • Try everything!!! It's all perfect.
  • Highly recommend on a beautiful evening. The Tajarin really won me over (delicate, flavorful, just perfect), but everything was very, very good.
  • The summer menu features snacks like gougeres w/ lemon caper whipped goat cheese and chow chow relish, and light cocktails like the "Violet You're Turning Violet" w/ blueberry Veev, cava, and lemon.
  • Lovely rooftop. Breadbasket. Chicken skins. Mussels if they don't run out ( which they have the past 3x I've been) all great!!
  • Garden to table, amazing atmosphere, small but inventive menu, good drinks, very easy to stay for several hours just shooting the breeze (and it's real breeze!)
  • The garden rooftop is gorgeous and peaceful. Went with a group and got to sample a lot - bread basket and chicken skins are a must app and the corn dessert was delicious.
  • Fettuccine with rabbit-pork meatballs and nettle pesto is considered a small dish on the menu, but it's plenty satisfying.
  • This 80-seat rooftop restaurant is a virtually perfect urban oasis.

Nearby places

1924 W Chicago Ave (at N Winchester Ave)
1938 W Chicago Ave (btwn Winchester Ave & Damen Ave)
1916 W Chicago Ave (btwn Winchester Ave. & Wolcott Ave.)