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Party Size
For 2
7:00 PM
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Upstairs at The Gwen

56 reviews
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$30 and under
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Top Tags:
  • Bar Seating
  • Great for Lunch
  • Quiet Conversation
Highlighting the rich diversity of American cuisine, Upstairs at The Gwen serves three meals a day in an elegant space that gives a wink to Chicago’s storied past. Located on the 5th floor, Upstairs offers a variety of seating options — from cozy banquettes to communal tables — allowing guests to tailor their dining experience. For groups, Upstairs at The Gwen also offers private dining rooms, which can be reserved for intimate affairs, special occasions, and events.

Perched on the fifth floor of the landmark McGraw-Hill building, Upstairs at The Gwen focuses on the art of craft cocktails paired with shareable small plate fare, and boasts cityscape views from among the Art Deco-infused architecture of The Gwen.
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Private dining
Dining Style
Casual Dining
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American, Farm-to-table
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Hours of operation
Circa Restaurant
Breakfast: 6:30 am - 11am

Upstairs at the Gwen
11 am -12 am (Sun-Thurs)
11 am-2 am (Fri-Sat)

Upstairs at The Gwen, an outdoor dining experience (seasonal; weather permitting),
Sunday through Thursday: 11:00 am - 11:00 pm
Friday and Saturday: 11:00 am - 12:00 am

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Phone number
(312) 645-1500 ext. 4800
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Payment options
AMEX, Diners Club, Discover, MasterCard, Visa
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Dress code
Casual Dress
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Executive chef
Matt Jergens
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Cross street
Between Grand Ave. & Illinois St.
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Parking details
We do not validate parking.
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Public transit
CTA: Red Line Train ("Grand" Stop)
Bus: 147, 148, 151, 145, 146, 3, 157
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Special events & promotions
Join us for live music every Wednesday and Friday
Banquet, Bar Dining, Bar/Lounge, Beer, Cocktails, Corkage Fee, Entertainment, Fireplace, Full Bar, Happy Hour, Non-Smoking, Outdoor dining, Private Room, View, Weekend Brunch, Wheelchair Access, Wine

Private Dining

Conveniently located off the Magnificent Mile, The Terrace Restaurant evokes a relaxed environment for you to host anything from your next corporate event to family celebration.

View Private Dining Details
What 56 People Are Saying
Overall ratings and reviews
Reviews can only be made by diners who have eaten at this restaurant
3.9  based on recent ratings
Noise · Moderate
63% of people would recommend it to a friend
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vipPamo1111 (Chicago)
3.0  Dined on February 5, 2018

Service was slow at lunch during Restaurant Week. It seemed they were understaffed. The food was excellent.

ALB1000 (Chicago)
3.0  Dined on February 3, 2018

Food was mediocre and overpriced. Service was lacking and ambiance left a lot to be desired.

vipRecessionista (Chicago)
1.0  Dined on February 1, 2018

Upstairs at the Gwen cancelled our reservation giving no reason. After attempting to contact them twice, we gave up and made reservations elsewhere. We found out later that there was a private event happening that night, which we would have understood if they had bothered to let us know. So, the low marks are for never getting our feet in the door in the first place and therefore not being able to evaluate anything.

OpenTable Diner (Chicago)
3.0  Dined on January 31, 2018

Restaurant week-lunch date. Service horrible
No one or host for 15 mins when we arrived. Didn’t offer beverage. My husband had to walk up to the bar twice. Once for beer, once for pepper for our pasta

OpenTable Diner (Chicago)
5.0  Dined on January 29, 2018

Went for Restaurant Week and the $33 value was definitely worth it! The food was great. Highly recommend the Grilled Octopus and the Wagyu beef. My only complaint is that this wasn’t an actual restaurant, it’s the bar/lounge in the hotel lobby. Slightly misleading, but still enjoyed dinner.

vipJoanne (Phoenix)
4.0  Dined on January 28, 2018

We dined here during Chicago's restaurant week! Contemporary and warm atmosphere and decor. Three course meal was delicious, server was attentive, and cocktails/wine were tasty.

Next time when warmer weather arrives, we'll return to Dine on their awesome rooftop bar.

vipOpenTable Diner (Chicago)
4.0  Dined on January 20, 2018

We went for the rooftop patio and curling, and had an amazing time! It is a great spot to meet friends and enjoy the city!

vipapple (Chicago)
5.0  Dined on January 20, 2018

food is not something what impressed me, but overall atmosphere was very nice. interior is pretty cool and comfortable. nice place. was not busy at all. locate at the Gwen hotel on the 5th floor i believe. they also have very nice patio. since we`ve been there in January, they do not serve drinks or food there, but probably during the summer time that is going to be a hot spot. service was very good also. and their prices surprised us...

OpenTable Diner (Chicago)
2.0  Dined on November 23, 2017

I’m in the hospitality industry and understand mistakes. This was a big one. Overall, negative Thanksgiving experience. Barely a major holiday effort by management. Under-staffed, no live music, I mean not even a harpist or something? My friends and my food coarses and sides came out all at different times, drinks took forever once we sat down, no real holiday element. 2 out of 10 rating, just for the food. Embarrassing effort.

vipOpenTable Diner (Chicago)
4.0  Dined on October 21, 2017

We visited after a show at the Chicago Theater. We'd eaten a very late lunch so we weren't starving, but wanted to have a light meal and some drinks. What a beautiful outdoor space, and even on this gorgeous night wasn't wall-to-wall people (but nicely full and lively). Loved the fire feature. Loved our cocktails. We shared a fantastic cheese plate and huge, delicious salad. I would definitely go here again.

scarlet5 (Chicago)
3.0  Dined on September 23, 2017

Service was poor. We were not greeted and just sat ourselves. Took a long time for a server to greet us and get menus and then even longer for our order to be taken and then a long time to receive our drinks. The atmosphere was very nice but was also very pricey. Not worth the price of drinks and poor service

OpenTable Diner (Chicago)
5.0  Dined on September 22, 2017

Unique selection of cocktails, great food, and lovely ambiance. Excellent service. Would love to see an expanded menu of entrees. A little on the expensive side, but we would definitely go back! :)

scarlet5 (Chicago)
1.0  Dined on September 2, 2017

I unfortunately did not get to dine or get a drink at the restaurant. Apparently they scheduled a private party and I was not notified. I specifically came in from the suburbs for that night to meet a friend. We arrive for a reservation and are then told there is a private party. This was Labor Day weekend, we were just told sorry and turned away. We basically had to just walk around and find somewhere else to go. I could have made a reservation elsewhere if I had known. I was extremely upset

vipqlbabs (Chicago)
5.0  Dined on August 27, 2017

This isn't our favorite outdoor spot in the city! Great service, food, drinks, ambiance, and view.

vipTeri (Chicago)
5.0  Dined on August 25, 2017

We were in town for a girls day and happened to stumble on this gem. We thoroughly enjoyed our dinner, our server (sorry i don't remember her name) and the atmosphere. Would definately recommend and go back.

OpenTable Diner (Chicago)
5.0  Dined on August 11, 2017

This was a very chic place with a great view of the city. The food was great as well as the ambience. I will definitely return.

OpenTable Diner (Chicago)
4.0  Dined on July 30, 2017

I overall enjoyed my visit , the decor from the lobby, to the lounge/bar, to the outside where superb! The view was a little lackluster for me, I was under the impression that the rooftop would have a better view of the city but I still enjoyed it. They had a lot of near by parking options and the location was easy to get to. The food was tasty and had a decent price point. The positives end there... they had TVs playing Big Bang Theory which killed the mood for me. I was not amazed by the service, we felt forgotten majority of the time. My biggest pet peeve was the amount they charged ($42!) for a bottle of cheap wine that I could buy at the store for $15 like come on.. when I'm about to drop $150+ on a dinner for 2 I better have great service, good food, and a good glass of wine if not then it's no better than going to a Dave and Busters but save some money.

OpenTable Diner (Chicago)
3.0  Dined on July 29, 2017

Horrible service, sat for 20 minutes before a waiter came to take order for drink, brought or drinks then didn't come back for a half hour to take food order, needless to say, we didn't stay for food

girlindc (Adelaide / SA)
3.0  Dined on July 22, 2017

Could have been better. The waitress didn't really know what she was doing. The food was fine but took a super long time to bring out to us. They charge $42 for a bottle of wine that is $12 in grocery stores. Not ideal.

vipJettDee (Detroit)
1.0  Dined on July 16, 2017

The service was really slow. My wife ordered a burger and fries and it was over an 1 hour and a half. The restaurant wasn't even busy so I'm not sure why it took so long. I recommend going to the food court next door to get food. It's a lot faster and cheaper.