The Windsor

4.4
170 reviews
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$30 and under
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American
The Windsor is your neighborhood restaurant in a downtown locale, welcoming guests to sit back relax and enjoy a casual dining experience just off the hustle of the Magnificent Mile. Chef Todd Stein"s inventive romp through a classic American Bar and Grill features fresh seafood, hearty entree salads, amazing steaks, delicious chops, and mouth-watering prime rib from the rotisserie. The Windsor will bring a sense of comfort and friendly service for which the neighborhood restaurants of 4-Star Restaurant Group are known to Streeterville. Dressed up or dressed down, come in, sit back and let us take care of the rest.
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Private dining
Dining Style
Casual Dining
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Cuisines
American, Comfort Food, Gastro Pub
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Hours of operation


Brunch: Saturday & Sunday: 10:00am - 3:00pm; Lunch: Daily: 11:00am - 3:00pm; Dinner: Sunday - Thursday: 3:00pm - 10:00pm, Friday & Saturday: 3:00pm - 11:00am
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Phone number
(312) 943-7777
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Payment options
AMEX, Discover, MasterCard, Visa
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Dress code
Casual Dress
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Executive chef
Nolan Narut
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Cross street
St. Clair
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Parking details
There is a valet conveniently located at the entrance to the Hotel, on Huron Street.
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Public transit
Michigan Avenue Bus stop is 1/2 a block from our front door at the intersection of Michigan and Huron.
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Entertainment
Sunday, December 20, 2015 we will be hosting a Santa Brunch from 11 - 2
Additional
Banquet, Bar Dining, Bar/Lounge, Beer, BYO Wine, Cafe, Corkage Fee, Fireplace, Full Bar, Happy Hour, Late Night, Non-Smoking, Outdoor dining, Private Room, View, Weekend Brunch, Wine

Private Dining

Whether celebrating a special occasion with family and friends or hosting a corporate outing, The Windsor can accommodate all your special event needs.

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Specials

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Sun 10:00AM - 2:00PM
Sat 10:00AM - 2:00PM

What 170 People Are Saying
Overall ratings and reviews
Reviews can only be made by diners who have eaten at this restaurant
4.4based on recent ratings
4.3
food
4.3
service
4.2
ambience
4.1
value
Noise · Moderate
78% of people would recommend it to a friend
5
4
3
2
1
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JV
1 review
Dined 5 days ago
Overall 5food 5service 5ambience 5

Loved this place! The Mac n cheese app was delicious! Quiet and cozy, great spot for a date!

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OT
Chicago
1 review
Dined on August 24, 2018
Overall 5food 5service 5ambience 4

Hanger steak was terrific

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RF
Chicago
5 reviews
Dined on August 20, 2018
Overall 4food 4service 4ambience 4

The Windsor turned in a solid performance this week for a casual dinner! The service was fast and friendly (thanks, Colin), the soup and chicken dip sandwich were very good, and the beer was cold and good too. The place was lively without being loud, and the prices were very fair, considering its location and quality of food and service. I plan to return!

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KE
Nashville
6 reviews
Dined on August 11, 2018
Overall 4food 4service 5ambience 4

Sat outside. Artichoke dip nothing to write home about but good. Salmon was excellent. Perfectly cooked.

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MJ
London
8 reviews
Dined on August 5, 2018
Overall 3food 3service 3ambience 3

This restaurant was definitely not the highlight of our evening (maybe it was an off-night there). I had planned a birthday dinner there with 12 ppl. Open Table only lets you book a table for 11, so after calling, I was informed that the event planner would need to be involved if the party was more than 11. After talking to her manager, the host on the phone said 12 would be not issue, which was great. She said if we had more ppl coming, to call because there were other large parties scheduled. When arriving at 9pm (shortly after our allotted time), I was shocked to see the restaurant almost EMPTY! Was sad that there was no "buzz" at this place on a Friday night, made our birthday celebration very quiet. Food was good, not amazing or exceptional, but good. With SO many restaurants in Chicago, I doubt I'll be back ... manager seemed very nice though.

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MS
1 review
Dined on July 24, 2018
Overall 5food 5service 5ambience 5

Chef Bryan is the best in Chicago. Great management and wait staff.
We had heard great things about the Windsor and our experience surpassed all of our already high expectations.

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OT
San Francisco
8 reviews
Dined on June 29, 2018
Overall 4food 3service 4ambience 4

Lunch is pretty good but nothing super special. Really nice patio and the service team were on it. Great happy hour!

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D
Chicago
18 reviews
Dined on June 27, 2018
Overall 5food 5service 5ambience 5

Nice place to grab lunch by the hospital. Got the fish and chips and it was great. Service was attentive as well.

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LI
New York Area
9 reviews
Dined on June 23, 2018
Overall 5food 5service 5ambience 5

Such a great spot. Wait staff on point. Food was amazing

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OT
Toronto
1 review
Dined on June 8, 2018
Overall 4food 4service 5ambience 4

Had a nice experience. Wait staff was in their game - my wife was debating between two wines and decided on one. they came back with a pour of each, so she could decide.

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A
Chicago
108 reviews
Dined on June 1, 2018
Overall 4food 5service 4ambience 4

Excellent lunch option. Menu is not overwhelming but filled with excellent options. The mushroom soup special was terrific. It went well with an interesting selection of small plates, varied salads and burgers. There also was a selection of full plate “dinner entrees.”

Everything was well prepared and nicely presented.

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OT
1 review
Dined on May 26, 2018
Overall 1food 1service 2ambience 3

The service was very slow and most of the restaurant was empty. I ordered a cheeseburger med-rare. It came out well done. I sent it back and the rest of my party ate. When my burger came, the top bun was burned black. While they re cooked my burger they let me eat the cold fries they had served with it. Everyone else at my table did not feel their food was worth the price

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RD
Nashville
3 reviews
Dined on May 13, 2018
Overall 3food 3service 3ambience 4

Food did not come out at the same time...biggest complaint. Food was just so so. Expected more of an experience-better food for the price. Never asked if we wanted dessert, or if we were celebrating a special occasion, or checked on us enough, or if we wanted separate checks, etc. It was my son’s college graduation dinner and it was a very disappointing experience!

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OT
New England
1 review
Dined on May 11, 2018
Overall 5food 5service 5ambience 5

Great experience, great food!

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OT
Chicago
1 review
Dined on May 6, 2018
Overall 4food 4service 5ambience 4

It a good brunch spot!

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VV
Chicago
14 reviews
Dined on May 5, 2018
Overall 5food 4service 5ambience 5

While the turkey burger was a bit on the salty side this time, overall meal was great! Service was also friendly and prompt. One of our local favs for sure!

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J
Minneapolis
16 reviews
Dined on May 4, 2018
Overall 5food 5service 5ambience 5

Tried this place for the first time and loved it. Exceptional guacamole.

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D
Chicago
237 reviews
Dined on May 4, 2018
Overall 2food 2service 4ambience 2

Good waitress but food not all that good!

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RS
1 review
Dined on April 29, 2018
Overall 5food 5service 5ambience 4

The staff was cordial and food was great. Lots of vegan and vegetarian options.

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PL
Birmingham
1 review
Dined on April 28, 2018
Overall 5food 4service 5ambience 5

The crab toast appetizer was delicious. The chips and onion dip appetizer only provided a few chips not enough for the amount of dip. We requested additioal chips and were charged additional amount on our bill for just a handful of chips. Not worth the charge.
Great wine.

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OT
Chicago
9 reviews
Dined on April 27, 2018
Overall 5food 5service 5ambience 5

Great service. Delicious food.

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CD
Chicago
56 reviews
Dined on April 19, 2018
Overall 5food 5service 5ambience 4

Great lunch with a business associate. Food and service were great. We will be back.

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E
Chicago
16 reviews
Dined on April 1, 2018
Overall 4food 4service 4ambience 4

Nice little spot- pretty decor. Basic menu- good plain old American food- great deviled eggs, hamburgers, french fries. Hamburgers come with a nice brioche bun- nice touch. Great mac and cheese made with spaetzle . Friendly staff. Good location. Was there on a Sunday morning and liked that they had brunch and lunch at the same time.

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FD
St. Louis
4 reviews
Dined on March 24, 2018
Overall 4food 4service 5ambience 3

American fare. Good music piped in. TV sets around bar area. 😳😱

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OT
Chicago
1 review
Dined on March 19, 2018
Overall 5food 4service 5ambience 5

Great service . Tasty food and drinks. Beautiful interior.

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R
Chicago
8 reviews
Dined on March 18, 2018
Overall 3food 3service 4ambience 5

Went for brunch and restaurant had run out of bacon and sausage by 1:00 pm. Disappointing. Food otherwise good

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T
1 review
Dined on March 16, 2018
Overall 5food 4service 5ambience 4

Very good service--friendly and helpful waiter. Food was very good--the crab special was great! Reasonable prices for both drinks and food. Great young person place.

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JB
Chicago
10 reviews
Dined on March 4, 2018
Overall 4food 4service 4ambience 4

Ate here because it was a block from my hotel. Food was very good, service was friendly. It was nice to find a low-key restaurant close to Michigan Ave. on a Saturday night.

My only minor quibble is that I changed my order a couple of minutes after ordering, substituting brussel sprouts for mashed potatoes, but my food came out with mashed potatoes. But they brought the brussel sprouts too and made everything right.

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OT
Chicago
2 reviews
Dined on March 2, 2018
Overall 5food 4service 4ambience 4

Great happy hour

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CN
Chicago
5 reviews
Dined on February 14, 2018
Overall 5food 5service 5ambience 5

We stopped in for lunch on a weekday and had a good time.

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KB
Chicago
1 review
Dined on February 10, 2018
Overall 5food 5service 5ambience 5

The Cod was really good mixed with the coleslaw. I live in the west burbs I will most def come back again. Hospitality was second to none.

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JB
Chicago
14 reviews
Dined on February 10, 2018
Overall 3food 4service 1ambience 3

The service was very slow. We were overdressed for the environment as it is an upscale bar, but my boyfriend was wearing a suit and me a skirt when everyone else was pretty casual. The deviled eggs were delicious as was the mac and cheese. Great food, but slow service for dinner.

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OT
Chicago
1 review
Dined on February 2, 2018
Overall 3food 4service 3ambience 4

Good place for a standard meal but a really bad deal for restaurant week. They served mini portions of the app and desert which made it impossible to get your money’s worth even if you picked the most expensive options. But if I was coming here for an ordinary meal and paying menu price, it would be a decent value

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J
Chicago
3 reviews
Dined on January 26, 2018
Overall 5food 3service 5ambience 5

Wonderful and attentive service!

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P
Cincinnati
16 reviews
Dined on January 19, 2018
Overall 4food 4service 5ambience 3

Great place for a drink with a date. We enjoyed the food and the server was nice

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OT
San Francisco
1 review
Dined on January 19, 2018
Overall 4food 5service 5ambience 5

Nice spot to eat. Good food and service. The only reason it doesn't get 5 stars is because the table next to us was really loud, drunk, and SHOUTING the "f" word every other sentence. Very unnecessarily annoying.

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CD
Chicago
55 reviews
Dined on January 16, 2018
Overall 4food 4service 4ambience 4

Overall a great meal. The deviled eggs are not to be missed. Great old fashioned at the bar. Scallops with grits cooked perfectly. We will be back.

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NG
Chicago
7 reviews
Dined on January 13, 2018
Overall 4food 4service 4ambience 4

Good food and nice ambiance. We were there on a Saturday night and it was very quiet.

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r
Atlanta
9 reviews
Dined on December 31, 2017
Overall 4food 3service 5ambience 4

Food was kind of blah 🤷🏾‍♂️

But service was 👍🏾

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OT
Orlando
1 review
Dined on December 26, 2017
Overall 5food 5service 5ambience 5

Really good steak, really good service. Enjoyed my date with my wife.

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