Homestead on the Roof

4.5
icon/ic_reviewCreated with Sketch.
607 Reviews
icon/ic_price_rangeCreated with Sketch.
$31 to $50
icon/ic_cuisineCreated with Sketch.
Contemporary American

Need to book at 1:22 PM?

View all

About

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 Jesse Badger.

The warm & cozy interior features a seasonally rotating tasting menus, which incorporates ingredients from our own farm and local vendors into our nationally recognized cuisine.

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.
icon/ic_private_diningCreated with Sketch.
Private dining
Dining Style
Casual Elegant
icon/ic_cuisineCreated with Sketch.
Cuisines
Contemporary American, Tapas / Small Plates, Farm-to-table
icon/ic_clockCreated with Sketch.
Hours of operation
Dinner
Tue–Sat 5:00 pm–10:00 pm
icon/ic_phoneCreated with Sketch.
Phone number
(773) 332-2354
icon/ic_new_windowCreated with Sketch.
icon/ic_paymentCreated with Sketch.
Payment options
AMEX, Diners Club, Discover, MasterCard, Visa
icon/ic_dress_codeCreated with Sketch.
Dress code
Smart Casual
icon/ic_chefCreated with Sketch.
Executive chef
Jesse Badger
icon/ic_cateringCreated with Sketch.
Catering
Homestead on the Roof does have the capabilities to cater outside events and venues. Please email Morgen McGarrie for more information mmcgarrie@thefifty50.com
Open Google Maps
icon/ic_locationCreated with Sketch.
icon/ic_neighborhoodCreated with Sketch.
Neighborhood
icon/ic_cross_streetCreated with Sketch.
Cross street
Winchester (entrance is through ROOTS HANDMADE PIZZA)
icon/ic_parking_detailsCreated with Sketch.
Parking details
Metered parking available all along Chicago Avenue & Winchester.
icon/ic_public_transitCreated with Sketch.
Public transit
Damen Ave "50" CTA bus. Chicago Ave "66" CTA bus.
icon/ic_entertainmentCreated with Sketch.
Entertainment
None
icon/ic_special_eventsCreated with Sketch.
Special events & promotions
For special events, please email Jacklyn Seavern, Jacklyn@homesteadparties.com
Homestead is available for private dining and buyouts.
Our culinary team will work with you to craft menus to fit your specifications.
We do have catering menus for all types of price points and options that include chef stations, plated dinners, and open bar.
Please email Jacklyn for a copy of our menu and we will set a time to discuss a custom menu with our Chef Team.

Homestead on the Roof also caters for larger outside venues at The Bridgeport Art Center, Baderbrau, The Rookery and Studio Manarchy.

Additional information can be found on our website, www.homesteadontheroof.com
Additional
Banquet, Bar/Lounge, Beer, Cocktails, Full Bar, Non-Smoking, Outdoor dining, Private Room, View, Wine
avatar copy

Private Dining

Book your next event with us

View details
What 607 People Are Saying
Overall ratings and reviews
Reviews can only be made by diners who have eaten at this restaurant
4.5based on recent ratings
4.4
food
4.2
service
4.7
ambience
4.0
value
Noise · Quiet
93% of people would recommend it to a friend
5
4
3
2
1
Sort by
Filters
CA
1 review
Dined on September 25, 2019
Overall 5food 5service 5ambience 5

AN exquisite experience in a relaxed unpretentious delivery and wonderful staff.

OT
New York Area
14 reviews
Dined on September 20, 2019
Overall 2food 1service 4ambience 5

Nice atmosphere-horrible food.

SG
Chicago
2 reviews
Dined on September 19, 2019
Overall 4food 4service 4ambience 5

It was stunning. Such a hidden gem. The drinks were amazing and the bread basket was to die for. Service wasn’t the fastest but I didn’t mind, I was there on a date, in no rush. I had the fried chicken and my boyfriend got the duck, both were huge portions and very tasty. Highly recommend!

TT
1 review
Dined on September 19, 2019
Overall 5food 5service 5ambience 5

Of all the place I have eaten in Chicago this was the best! The service was quick and friendly and the food was delicious and artistically plated. I will definitely go back the next time I am in Chicago!

AD
Chicago
1 review
Dined on September 18, 2019
Overall 5food 4service 3ambience 5

Everything was fabulous, as usual, but our food took a really long time from when we ordered.

m
Chicago
13 reviews
Dined on August 30, 2019
Overall 1food 1service 1ambience 4

They just seem a bit disorganized. We were seated and asked to move, nobody really came to help us. Our server was off, my drink came but my husbands took at least another 10 minutes, our water was never refilled and basic asks took forever. The food was mediocre at best, nothing worth returning for. We had the mussels that were small and pretty flavorless (even though presentation was good), husband had the shrimp and grits, and i had the pork/bacon burger. Honestly i think the place is surviving off the cool atmosphere they have on the roof during the summer.

OT
Chicago
1 review
Dined on August 29, 2019
Overall 5food 5service 5ambience 5

So incredibly delicious! Absolutely amazing.

A
Chicago
19 reviews
Dined on August 29, 2019
Overall 3food 2service 5ambience 4

Way too pricey for what you get!! Spent 140dls on dinner for 2 with 1 cocktail, 2 appetizers, an entree and a side salad (the entree was shrimp and grits, 5 shrimp and maybe 3 spoonfuls of grits). The rooftop is lovely and the flavors nice but needlessly small portions!

MK
1 review
Dined on August 24, 2019
Overall 5food 5service 5ambience 5

What a gem in the middle of Ukrainian Village/West Town. I had the steak frites and my husband had the half duck. Our meals were personally delivered by the chef who checked in with us during the meal. The space was open and inviting with garden vegetables growing in every corner. Would definitely recommend for date night.

C
Chicago
5 reviews
Dined on August 23, 2019
Overall 2food 1service 2ambience 4

The ambiance is very nice hoqever

OT
Chicago
8 reviews
Dined on August 23, 2019
Overall 3food 2service 1ambience 3

Overall pretty disappointed. The service was absolutely terrible. The food was fine besides the fried chicken- that was awesome. The walleye was so fishy we had to send it back.

L
Washington DC
3 reviews
Dined on August 20, 2019
Overall 5food 5service 5ambience 5

The food speaks for itself. Every dish was phenomenal and our waiter knew every little detail about the menu.

OT
Chicago
1 review
Dined on August 16, 2019
Overall 5food 5service 5ambience 5

Outstanding birthday dinner - truly one for the books. Incredible service, food, and cocktails!

OT
Chicago
3 reviews
Dined on August 8, 2019
Overall 3food 2service 2ambience 5

I was really excited to go to Homestead and unfortunately I was pretty disappointed. While the outdoor setting is great, the service and food were not so great. The service was incredibly slow - felt like we were there for hours and most of the time was spent just waiting to order! The salads, which contain ingredients from the garden were pretty good. The apps we ordered were small, lacking in flavor, not what we were expecting and overall disappointing. For example, the raclette was an incredibly tiny portion of cheese served in a huge cast iron skillet with only 2 pieces of bread and like 5 potatoes - definitely not worth it for the price. The tomato tarting was a large piece of bread with a bunch of tomatoes and cheese just sprinkled on top - again not very interesting. By far the most disappointing was the entrees. The mushroom fregola tasted like straight up vinegar and you couldn’t taste the mushrooms at all- I almost wanted to send it back. Other entrees, such as the walleye, were incredibly average. I was super bummed about our experience as I’ve read so many good reviews but I can’t say I’ll be back or would recommend it.

ML
Chicago
1 review
Dined on August 6, 2019
Overall 5food 5service 5ambience 5

I loved this restaurant. The waiter was very entusiastic about the menu. It was as good as his description. We had the artichoke parmesean fritter for an appetizer and it was delicious. The roast duck was as tender as butter and the roasted vegetable soup was fabulous. I plan to go again.
Loved it

AF
1 review
Dined on August 3, 2019
Overall 5food 5service 5ambience 5

Anthony was amazing and the atmosphere was soo good! We only had dessert and drinks but judging by how passionate Anthony was about the food we will certainly be back for more. The dessert was outstanding and the cocktails were incredible!

MK
Chicago
2 reviews
Dined on August 3, 2019
Overall 5food 5service 5ambience 5

Everything was amazing (the meal, the service, the views/ambience) my new favorite spot in the city. Can not wait to go back!

GH
1 review
Dined on August 1, 2019
Overall 2food 4service 1ambience 1

Had a reservation for 8:30, wasn’t seated until 9. Bartender was rude while we waited, not enough lights had to use flashlight to see menu, poor service from waiter. Food was really tasty but I wouldn’t recommend.

EB
1 review
Dined on July 30, 2019
Overall 5food 5service 5ambience 5

We made a reservation at a recommendation from a co-worker and really enjoyed our experience. Service was fabulous and the ambiance was remarkable. Our meals were delicious. Staff was extremely pleasant. We would definitely return.

OT
Chicago
2 reviews
Dined on July 25, 2019
Overall 3food 2service 2ambience 4

Great atmosphere. Food is fair to poor and service is unremarkable. More expensive than it should be. Too bad because it’s a great space.

S
New Orleans
35 reviews
Dined on July 24, 2019
Overall 5food 5service 5ambience 5

Great date spot

JA
Chicago
1 review
Dined on July 24, 2019
Overall 4food 3service 5ambience 4

My shrimp dish was very tasty although awkward having to peel the shrimp.
My husband had the fish which he said was fair at best.
I thought it was pricey for what we got although the service was excellent.

YB
Chicago
1 review
Dined on July 23, 2019
Overall 3food 2service 4ambience 5

The food was very mediocre for a restaurant that prides itself on fresh produce and herbs.

OT
Calgary
1 review
Dined on July 19, 2019
Overall 5food 4service 4ambience 5

Such cool atmosphere, amazing food & service! Would recommend!

OT
Chicago
2 reviews
Dined on July 17, 2019
Overall 5food 5service 5ambience 5

Excellent! Great atmosphere, food was outstanding, great date spot but several other groups dining around us, waiter was the best! Sat outside, but has a decent space inside as well (get outside!).

The only weird thing is walking through Roots Pizza and up a back stairwell until you find this place... there's a sign hanging at front of Roots Pizza entrance, and had to go in and ask where to go

LM
Baton Rouge
1 review
Dined on July 13, 2019
Overall 4food 4service 4ambience 5

I had the special filet. It was the toughest filet I’ve ever had. And, the most expensive!!

OT
Chicago
1 review
Dined on July 13, 2019
Overall 5food 5service 5ambience 5

Everything was wonderful from the service to the food to the ambiance. We enjoyed the entire experience. Our food had layers of flavors that were unique and delicious.

CN
Chicago
6 reviews
Dined on July 12, 2019
Overall 4food 5service 3ambience 5

The atmosphere was fantastic and area is beautifully decorated. The food tasted delicious, highly recommend the raclette for an app! However the entree portions definitely didn't match... my fried chicken had 5 large pieces while my boyfriend's steak frites had a tiny portion of meat. Service was good but the waiter seemed timid and then sort of disappeared when it was time to bring the check.

OT
Chicago
8 reviews
Dined on July 10, 2019
Overall 4food 4service 4ambience 4

Perfect local rooftop

N
Chicago
15 reviews
Dined on July 6, 2019
Overall 3food 2service 3ambience 2

The past two years my husband and I had enjoyable anniversary dinners at Homestead on the Roof. This year we included another couple, promising a wonderful experience. Of course no one can control the wind. It was too gusty for our comfort so we requested to be seated inside. I had made the reservations 3 1/2 weeks prior. I wasn’t told of the West side fest. The band and crowd noise would’ve been even more annoying if we had sat outside.
The menu was not as good this time around. The chef did accommodate my dietary restrictions, but truly, the menu lacks for not having a couple of vegan options (no gluten would be a big help as well as I am also gf/df, not by choice). My husband and the other couple are adventurous foodies, and they too were disappointed in the offerings. Our server was good, friendly. However at the end of the meal, check and payment became a slow process. I’d like to try again but only if the menu had some other offerings that made it much easier for a person like myself to find something. The chef did make a concerted effort this time around. He made something from veggie ingredients available, which was creative.

OT
1 review
Dined on July 3, 2019
Overall 5food 4service 4ambience 5

Great place for food and drinks
Rooftop patio makes the summer nights enjoyable

T
Chicago
1 review
Dined on June 29, 2019
Overall 5food 5service 5ambience 5

Incredible. Beautiful spot. Amazing food and drinks. Superb service. LOVED IT!!!

SK
1 review
Dined on June 27, 2019
Overall 5food 5service 5ambience 5

Perfect for a first date or casual dinner with beautiful ambience and scenes. Servers were super cool, friendly, and hospitable! I’ll be back!

R
Grand Rapids
2 reviews
Dined on June 27, 2019
Overall 5food 5service 5ambience 5

Awesome staff! It started storming after we already arrived. Ahead of time, they asked if they could move us underneath the awning. During the storm they were very attentive, kept great attitudes and were very accommodating. Awesome place, we plan on going back when the weather is nicer!!

g
Chicago
3 reviews
Dined on June 22, 2019
Overall 5food 5service 4ambience 5

Interesting, great tasting food and drink selections; well presented; and a good value for the quality! Our server was a bit intense (fast, a bit frantic talking) in his initial introduction (and we noticed this with his other tables as well), but overall likable. There wasn't much interaction after the food was brought to the table. My wife and I would've appreciated a brief "re-introduction" of the items we ordered when they were delivered (esp. since most dishes have at least 1 or 2 interesting/lesser known ingredients), but it didn't hamper our experience much. The ambiance is fantastic. It's peaceful and the tables are spaced appropriately for not being a part of others' conversations. My wife, being vegetarian, was able to find plenty of items from which to pick, though a lot of the veggie items this time around were mushroom focused. Overall, a great experience for our first time and we'll definitely be back.

l
Chicago
13 reviews
Dined on June 22, 2019
Overall 5food 5service 5ambience 4

The benches they have are not very comfortable and maybe could be updated or at least padded ?

LH
Atlanta
3 reviews
Dined on June 21, 2019
Overall 5food 5service 5ambience 5

This place is very serious about the food and service they provide to customers, and it's clear it is their passion. They take farm to table to new heights (pun intended). I had a dinner here to celebrate my graduation from business school, and the food and drinks were delicious. Highly recommended!

OT
Chicago
1 review
Dined on June 21, 2019
Overall 5food 5service 5ambience 5

Food was excellent. Service was fantastic. Drinks were very good.

r
Chicago
8 reviews
Dined on June 21, 2019
Overall 4food 4service 4ambience 4

Homestead is one of my favorite restaurants in the city. I've never had anything but a pleasant experience there, although I have to admit this past visit was a bit underwhelming. Service was ok, despite having to wait an hour for our first plate to arrive... Also had requested to sit outside, although was told it wasn't open when we arrived. An hour later the host was seating people outside... I'll chalk this up too an anomaly instead of the norm and hope to return soon.

OT
Detroit
2 reviews
Dined on June 21, 2019
Overall 3food 2service 4ambience 3

The Raclette was a good appetizer. The ramen was not a good main dish. The fried pork cube tasted like it was fried in month old grease. Wouldn't recommend!

1
2
3
16

Tweets by Homestead on the Roof