The Windsor

4.3
227 reviews
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$30 and under
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American
Good times are here at The Windsor! Steps away from Michigan Avenue on East Huron, patrons may enjoy a classic American meal at this Streeterville neighborhood hideout. The Windsor is the ideal spot to grab dinner and a drink while enjoying happy vibes and great conversation. The restaurant offers small plates, salads, sandwiches, and mains such as the Rotisserie Half Chicken and Berkshire Pork Chop. Happy hour is a great time to enjoy the restaurant’s delicious bar snacks, craft cocktails, and wine and beer selections. The Windsor is open daily for lunch and dinner.
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Private Dining

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What 227 People Are Saying
Overall ratings and reviews
Reviews can only be made by diners who have eaten at this restaurant
4.3based on recent ratings
4.1
food
4.3
service
4.1
ambience
3.9
value
Noise · Moderate
88% of people would recommend it to a friend
5
4
3
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MO
Chicago
20 reviews
Dined on June 16, 2019
Overall 3food 2service 5ambience 3

We were originally disappointed because the establishment no longer served brunch even though it clearly says it does on the menu. The service was the saving grace; it was superb.

The Windsor
Responded on June 17, 2019

MandelO, we appreciate you taking the time to share your feedback. We are happy to hear that you enjoyed the service, but hate to hear that you were misinformed about brunch no longer being served. We aim for a top-notch experience with all of our guests and we are very sorry that we dropped the ball this time around. We are working on updating all of our public menus/profile so this does not happen again. Please let us know if there is anything else that we can do to improve your experience.

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OT
Chicago
1 review
Dined on June 16, 2019
Overall 2food 2service 3ambience 2

We went for the bunch menu but when we arrived we asked for the brunch menu and they had done away with brunch that needs to be updated on the website menu.

The Windsor
Responded on June 17, 2019

Good morning, I am very sorry about your recent visit. We aim for the highest quality service possible and never want to misinform or let down our guests. Our team is working on updating our public profiles and menus. I know there are many choices for restaurants in and around the city and proper execution is key to staying on that list. Please reach out with any additional comments, questions, or if there is anything we can do to help improve your experience and ensure another visit. Thank you

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DB
Birmingham
50 reviews
Dined on June 6, 2019
Overall 4food 4service 4ambience 3

Pleasant pub-like place. Food and service were fine.

The Windsor
Responded on June 12, 2019

Thank you, DoctorBob!

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OT
Chicago
1 review
Dined on May 27, 2019
Overall 1food 1service 1ambience 1

Was not opened but still accepted my reservation

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TR
Chicago
3 reviews
Dined on May 13, 2019
Overall 5food 5service 5ambience 5

I enjoy eating here due to the proximity of the location. The food is very well prepared and delivered in a timely fashion. The waitstaff is very congenial and professional.

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DW
Chicago
12 reviews
Dined on May 12, 2019
Overall 2food 2service 2ambience 3

We went the afternoon of Mother day. There were about 20 people in the restaurant (should of been warning sign”. The food was just ok. Got the pork belly sliders. They tasted like nothing....actually they just tasted like the marmalade glaze that was smeared on the bun. Daughter got pasta..it was Olivia garden quality. The service was the worse. Had ask every time to get water refills. Asked for lemons for water, never brought them then would disappear for 10-15 minutes. Not a good experience for the cost.

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JM
1 review
Dined on May 11, 2019
Overall 5food 5service 5ambience 5

My family loved this restaurant. I would highly recommend trying this place. You will definatly want to return! The best fried clams ever!

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B
Chicago
73 reviews
Dined on April 24, 2019
Overall 3food 2service 2ambience 2

Marginal food/service. Place feels like a mid-priced hotel’s restaurant, which it is.

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JC
Chicago
24 reviews
Dined on April 19, 2019
Overall 5food 5service 5ambience 5

Lunch with my hubby

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CN
Chicago
6 reviews
Dined on April 15, 2019
Overall 5food 5service 5ambience 5

New employee lunch. Everyone enjoyed their food.

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s
Chicago
9 reviews
Dined on April 14, 2019
Overall 4food 5service 4ambience 5

Breakfast was very good. Service was a little slow and the restaurant was pretty empty but overall had a very good experience.

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WA
Chicago
3 reviews
Dined on April 10, 2019
Overall 5food 5service 5ambience 5

Great happy hour menu!

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OT
Chicago
1 review
Dined on April 3, 2019
Overall 3food 3service 2ambience 3

Waiter had order wrong then entire group was finished eating by the time the last person was served due to waiter error.

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4
Cleveland
5 reviews
Dined on March 30, 2019
Overall 5food 5service 5ambience 5

We went here for breakfast and it was absolutely wonderful. Great food and service! And the atmosphere is fantastic. We were there on a cold blustery Saturday. We sat by the cozy fireplace and watched the rain.

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G
Chicago
3 reviews
Dined on March 29, 2019
Overall 3food 2service 4ambience 3

The food is normally very good. This particular night the kitchen was off.... ... not a good experience.

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RH
1 review
Dined on March 29, 2019
Overall 4food 5service 4ambience 4

Had a great time food was great I kept it simple started with the ceasar salad that was great had a burger and that was outstanding also. My Wife has the chicken sandwich with the chicken au ju and a deviled egg and Brussels sprouts she thought sandwich was great but she was taking about hiwngood the Brussels sprouts and deviled eggs was the next day. The drinks where Ok made strongly and was decent price although it was happy hour. We will go be going back.

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D
Chicago
17 reviews
Dined on March 28, 2019
Overall 4food 5service 5ambience 4

Food and service were excellent- place was a bit noisy- bar service was good but very expensive

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LM
San Francisco
1 review
Dined on March 24, 2019
Overall 3food 3service 4ambience 3

I did not realize that the restaurant was attached to a hotel which indicates to me at least it's not frequented by locals. The food was decent, but not outstanding. I got a crab avocado toast that had soggy toast, and a mushroom soup that was incredibly too salty. I got a peach flavored cocktail that was super sweet as well...

The restaurant is nice inside, but not for brunch (when I went).

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DG
Chicago
1 review
Dined on March 23, 2019
Overall 4food 4service 5ambience 3

The Windsor was am ok experience! Our waiter was nice but the food was only ok. Enjoyed the monkey bread.

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m
Chicago
25 reviews
Dined on March 19, 2019
Overall 5food 5service 5ambience 5

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

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BF
Chicago
36 reviews
Dined on March 17, 2019
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 on March 16, 2019
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
131 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
2 reviews
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
Chicago
2 reviews
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
18 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
4 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
16 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
16 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
3 reviews
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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