The Windsor

4.4
208 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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Sun 10:00AM - 2:00PM
Sat 10:00AM - 2:00PM

What 208 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
4.4
food
4.4
service
4.3
ambience
4.1
value
Noise · Quiet
76% of people would recommend it to a friend
5
4
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m
Chicago
23 reviews
Dined 2 days ago
Overall 5food 5service 5ambience 5

Windsor is my favorite "go to lunch" spot. It is also good afterwork.

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BF
Chicago
32 reviews
Dined 4 days ago
Overall 5food 5service 5ambience 5

Enjoyed brunch at this place, they were very gracious and allowed me to modify my meal. Meaning, I ordered a standard plate but asked if I could add a protein on top of my eggs, not only did they do that but it was topped with fresh chives to add to the wonderful taste of my breakfast. Service was kind and very personable, truly a genuine experience.

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MR
1 review
Dined 5 days ago
Overall 5food 4service 3ambience 4

This was my first time visiting The Windsor and it was a great experience! I actually stumbled upon the venue while trying to find a restaurant in the area to host out of town guests. The server was awesome and the food was delicious. Definitely would visit again!

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m
Baltimore
2 reviews
Dined on March 6, 2019
Overall 5food 5service 5ambience 5

We were served next to the fireplace and expertly taken care of by Patrick: his cocktails and wine recommendations were matched by his expert food advice. The restaurant was cozy and intimate. It wasn’t packed which may have helped with that ambiance but we’d absolutely go again.

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M
Chicago
129 reviews
Dined on March 6, 2019
Overall 3food 3service 4ambience 5

I got here at the tail end of happy hour and the specials are good. $3 drafts, $5 wines and a $7 specialty bourbon drink. They also have some happy hour snacks and a $10 burger and fries, a steal for downtown Chicago. Very friendly and attentive server, Sarah. The regular menu is pricier, but you pay a premium for downtown so it's competitively priced in that respect. I really liked the burger. I also ordered the homemade chips and salsa. The chips were a 10, the salsa, maybe a 6. Too many onions and needed more spice.

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K
1 review
Dined on February 28, 2019
Overall 5food 5service 5ambience 5

I took my team to The Windsor for a celebration dinner. Service was unbelievably fast, friendly, and sincere. Food was delicious. Restaurant was beautiful and comfortable. My team loved the experience!

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OT
Chicago
1 review
Dined on February 23, 2019
Overall 4food 4service 4ambience 4

Great food with local ambiance.

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CM
1 review
Dined on February 23, 2019
Overall 2food 2service 3ambience 3

The service was good at the beginning of our night. My husband thoroughly enjoyed the beet salad, but then we waited a full 30 min before our meal came. My husband ordered a medium rare ribeye; it arrived completely white in the center. I ordered my steak medium and it was rare. The chef did come to aplogize & offered to redo our steaks, but we didn't have time to wait. I feel an adjustment on our bill would've been appropriate. Very expensive for a poorly cooked meal.

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LS
1 review
Dined on February 19, 2019
Overall 5food 5service 5ambience 5

Stopped by to catch some drinks and appetizers with a friend after work. Great draft and bottled beer selection as well as unique house cocktails. We split an appetizer and were very satisfied with the portion and price. The service was friendly.

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OT
1 review
Dined on February 17, 2019
Overall 3food 3service 4ambience 3

Seared scallops were not what I had hoped for. Basically the brown butter sauce overpowered the dish and made it taste like a burnt dish.

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JQ
Chicago
16 reviews
Dined on February 17, 2019
Overall 3food 3service 4ambience 3

We chose this restaurant due to the proximity of a play we were seeing that evening. The service staff was very attentive and nice. The menu is on the small side and somewhat limited. My chicken and mashed potatoes were tasty. The rest of our party all finished their meals as well, so they must have been satisfied with their choices. The décor of the restaurant is somewhat dated. The restaurant would rate only as an OK in my book. There are many other choices out there that would have been a better experience.

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MD
Chicago
9 reviews
Dined on February 17, 2019
Overall 4food 4service 5ambience 3

We had brunch here and overall enjoyed our meal. The Bloody Mary Frasca were nice and spicy. The roasted chicken hash was creative and well prepared. The omelette Streeterville was also interesting. Pat was our server. He was polite, friendly and helpful. Coffee was also good.

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EE
Chicago
6 reviews
Dined on February 14, 2019
Overall 4food 4service 4ambience 4

Food is and ambiance is good.

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LS
San Francisco
1 review
Dined on January 31, 2019
Overall 5food 5service 5ambience 5

Delicious dinner, quiet, and warm atmosphere. Loved it!

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RI
Chicago
2 reviews
Dined on January 4, 2019
Overall 5food 5service 5ambience 5

We had a group of 12 for lunch. Had an awesome time! Everyone loved their food, especially the brussels sprouts. Seriously! Overall everything was great - service, good and ambience. Will be back!!

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d
Chicago
21 reviews
Dined on December 30, 2018
Overall 4food 4service 4ambience 5

This had good reviews overall and I think it was fine. I went here for Sunday brunch with family and it was a little disappointing. The portions were small and left something to be desired. I don't think I will come running back here for brunch.

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OT
1 review
Dined on December 30, 2018
Overall 5food 5service 5ambience 5

Wonderful spot for brunch. the food was exceptional.

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D
Cincinnati
13 reviews
Dined on December 29, 2018
Overall 4food 3service 4ambience 4

I was very pleased with the Windsor. I had dinner there twice while in Chicago. Convenient place near the magnificent mile.

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D
Cincinnati
13 reviews
Dined on December 28, 2018
Overall 4food 3service 4ambience 4

I was by myself, staying at the Hampton, and it was easy to go to the Windsor. That atmosphere is very warm and cozy, I choose to be close to the fireplace. The service was attentive and the food I ordered was just right. Had dinner there twice.

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AM
1 review
Dined on December 28, 2018
Overall 3food 4service 1ambience 3

Food was really good but it took almost an hour to get our food- most of us ordered salads....

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FA
Detroit
1 review
Dined on December 28, 2018
Overall 4food 5service 3ambience 5

Very charming place and the food was excellent. Nice place for a nice dinner with friends!

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SF
Chicago
45 reviews
Dined on December 8, 2018
Overall 5food 5service 5ambience 5

Process were very reasonable for the location. All of the staff were encountered were very friendly. And being in the same building as our hotel was a plus.

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OT
Chicago
3 reviews
Dined on December 1, 2018
Overall 5food 5service 5ambience 5

Fantastic accommodations for a special evening.

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OT
Cleveland
2 reviews
Dined on November 30, 2018
Overall 3food 3service 5ambience 4

It's ok. Everything was good till the Hangar Steak. It was charred and I guess I'm not a fan of Chimichuri sauce.

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m
Chicago
24 reviews
Dined on November 28, 2018
Overall 5food 5service 5ambience 5

Windsor is a great lunch and dinner option. Friendly staff and love the simple menu, but good variety. Great drinks too! I eat there at least 3x a month.

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MM
Milwaukee
1 review
Dined on November 24, 2018
Overall 5food 5service 5ambience 5

Hidden gem. I didn't even want to share it but the food and service was so good I had to.

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R
Cincinnati
22 reviews
Dined on November 23, 2018
Overall 5food 5service 5ambience 5

Nice quiet bar/restaurant in bustling Chicago, with gas fireplace, super wait staff and delicious food. Super!

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DG
Chicago
1 review
Dined on November 21, 2018
Overall 2food 2service 2ambience 3

Everything about this experience was just OK, very consistent from beginning to end. We waited a bit too long for service at times, especially considering the place was not busy but when engaged the server was fine. Our food was all prepared as ordered and tasted OK, but several of the meals had been sitting awhile and were dry/not the proper temp. I would not recommend this restaurant.

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CK
Chicago
5 reviews
Dined on November 18, 2018
Overall 4food 5service 4ambience 4

The food was outstanding, the Sunday Brunch was pretty slow so we got right in and the food came out in decent time. Overall no complaints. We’ll definitely go again.

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CS
Milwaukee
3 reviews
Dined on November 3, 2018
Overall 4food 5service 5ambience 4

The server was extremely considerate and kind. Met all our needs and the food was fantastic.

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MD
Chicago
99 reviews
Dined on November 2, 2018
Overall 3food 4service 3ambience 3

We chose this restaurant due to it’s proximity to Northwestern Women’s Hospital. Our server, I think Jason, greeted us and was friendly although he chomped on his gum. Our table started sharing the deviled eggs, which were creamy, yummy and full of flavor. The deviled eggs had bacon and jalapeño with a touch of honey. We also shared the charcuterie plate. It was good, but smaller in portion size from others that I’ve had, especially the cheese portion. I asked for extra grilled bread which they did bring out which was appreciated. My dad had the rigatoni with sausage and peas, which he enjoyed. My mom and husband both had the mahi-mahi sandwich. The sandwich looked appetizing and both enjoyed their entrées as well. I opted for the sea scallops and asked for the chef to leave off the grits. Our waiter said he could do that and substitute asparagus instead...very nice...but the mushrooms and kale would be omitted too. Huh?? The kitchen could sauté the mushrooms and kale and still serve them on the plate with the scallops. Although I enjoyed the 4 scallops and 4 asparagus spears, it was very plain. It needed the mushrooms and kale. To ask not to have a carb so I would not be wasteful and yet not given the vegetables with the dish did not make sense. The price I paid for this entrée was not worth what I received. Once our entrées were served, the lack of attention began. I never had my water refilled and I couldn’t ask our waiter for a side of sautéed mushrooms as he never reappeared until we were all done eating and it was too late. Although this restaurant seems to be popular, I don’t think I will be back again. It’s a one and done for me for the lack of attention, the noise, lack of getting service once our meal was served and that even though they accommodated me by omitting the grits and giving me asparagus, they could not give me the rest of the meal which I paid for (the kale and mushrooms).

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RO
Chicago
11 reviews
Dined on November 1, 2018
Overall 5food 5service 5ambience 5

Good spot for a lunch meeting. Great food selections and prompt service.

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MP
Indiana
4 reviews
Dined on October 30, 2018
Overall 5food 5service 5ambience 5

Loved the caramelized onion dip with chips.

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OT
New York Area
1 review
Dined on October 26, 2018
Overall 5food 4service 5ambience 4

Great service, nice (if a bit loud) music as background sound. Food is filling and of very good quality. Creative flourishes on American classics (e.g., mac and cheese using spaetzle).

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AR
London
4 reviews
Dined on October 26, 2018
Overall 1food 1service 4ambience 2

Really poor quality food. Give it a miss unless you like tasteless overcooked chicken and awful sald. It's not often I have encountered such poor quality food in America

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HM
Chicago
2 reviews
Dined on October 21, 2018
Overall 1food 2service 1ambience 4

On Sunday at 11am, my friend and I were one of about 4 occupied tables. The waitress really rushed us to order, when we were undecided she became very flippant and rude and it was a tremendous inconvenience for her to take care of us. She brought the deviled eggs we ordered (each order is 1/2 of an egg) and was extraordinarily rude. When the main course was served, she never once came to check on how it was or to ask if we needed anything. The rotisserie chicken salad had gristle and vessels in it and it was not appetizing and she did not ever come back except to drop the check on the table. Overall, the food was not good and the service by our server was terrible. The host was very friendly, but after our experience, there is not a reason to return.

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D
Milwaukee
20 reviews
Dined on October 6, 2018
Overall 5food 5service 5ambience 5

Great food and service! It was a block off Michigan Ave and away from shopping chaos.

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A
Chicago
17 reviews
Dined on September 23, 2018
Overall 4food 5service 5ambience 3

Delish food & great service. We were hoping to sit outside but the striking hotel workers were distracting & noisy.

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JV
New England
2 reviews
Dined on September 15, 2018
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 23, 2018
Overall 5food 5service 5ambience 4

Hanger steak was terrific

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