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Squire On The Square

3.7 (55 reviews)
Closed • 11:00 am - 10:00 pm

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SQUIRE ON THE SQUARE ATMOSPHERE

What's the vibe?
Casual
Trendy
Dogs allowed
Happy hour specials

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Great Potato Skins with sour cream
Terri B.

Okay this is a tough one to write. Squire on the Square bar area was used in the movie Groundhog Day, so we really wanted to give it a try. The atmosphere is very cool, the place is quite big and good for large groups and family meals. The staff was so friendly, and I mean everyone. From the hostess who seated us and immediately told us that Happy Hour was ending in about 15 minutes and to order as soon as we could for any bottles of wine, beer or appetizers. I appreciate that. Our server came over to take our appetizer and drink order. We ordered a bottle of wine and an appetizer, the potato skins. She was so friendly and it was a pleasure chatting with her. The potato skins were delivered to our table and were actually delicious. They were crunchy and the cheese was perfectly melted and topped with bacon. While we enjoyed our potato skins, several servers and the restaurant manager stopped to check on us, which was so nice. Then it was time to order our dinner, and we were going a bit light. I chose to have a bowl of the soup of the day which was creamed corn soup. Mr. Bee decided to have the tuna tacos. Our dinner was delivered in a timely manner and this is where the disappointment came in. My soup was supposed to be cream of corn. it wasn't creamed, it was creamy, with pieces of chewy kernels. There was no seasoning, it tasted if it was just corn and milk or cream, not even any salt. I didn't finish it. Mr. Bee's tacos were odd. The tortillas weren't fried, just warmed and flimsy. The tuna was not like poke. It was shredded, cut, cooked through and not really appetizing. He ate some of the tuna out of the tacos, but nowhere finished his meal and I have never seen him not finish tuna tacos. So when I said this was hard to write, it is. The staff, from the hostess to the servers who jumped in and helped each other deliver food and clear plates to the restaurant manager who checked in twice, they were excellent. Where the downfall is is in the food. Nothing after the potato skins was seasoned, poke tuna tacos would be amazing and the creamed corn soup should have been pureed, with seasoning, maybe a little bacon on top. It was all just so bland and disappointing. So I am giving the staff five stars and the food earns two. It could be great!

Bbq brisket tacos - pass
Robyn W.

If you haven't visited downtown Woodstock, what are you waiting for? Squire on the Square had so much personality, with free popcorn for the table and charming medieval decor, this is a great spot for families. The flaming cheese is a must have and I the burgers are solid. The brisket tacos hit all the flavor points, but the meat itself appeared to be gyro meat. Stick with burgers and fries and enjoy this fun spot.

Saganaki imposter :(
Ashley B.

Must be Halloween and some other cheese dressed up as saganaki Because what we had did not taste like the saganaki we get from authentic Greek restaurants in Chicago. Let's get into the spicy prickly pear margarita next...well i hope you don't get into it because it's a waste. The smallest margarita with no depth of flavor, I think I've had tastier margaritas road side tbh. Service needs help-moments of one good bartender shined through out of the three who served us (we sat at the bar). Positive note (wooohooo) the sliders were good and we would order them again. The blue cheese was pungent and the pepper on top did some wonders paired with the sliders.

Onion soup
Donald M.

A wonderful place! Extremely professional service. The food is absolutely outstanding. The French onion soup is authentic -- the best I've ever had in Chicago! And the flavor of the Greek salmon truly transported me back to Greece. Thank you!

Our view from our table.   Sooooo pretty!

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2 months ago

Staff is nice and the food is consistent. Relaxing atmosphere and I love the popcorn.

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William L.

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10 months ago

Super great service. Food was ok. $100 for 3 of us. Saganaki was not cooked!melted. Loved the atmosphere.

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2 years ago

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6 months ago

Food, drinks, and service was amazing. We always enjoy coming here for dinner. I also love the commentary popcorn.

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1 year ago

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9 months ago

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1 year ago

Love this place. Amazing appetizers and the Prime Rib has the best smokey flavor. Cool atmosphere and huge outdoor seating

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2 years ago

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8 months ago

Our server Jenna was super nice, pina colada was superb and the spuds were great too! Cannot go wrong here.

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10 months ago

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1 year ago

Staff was very friendly, Restaurant setting was very nice and cozy. Food was not all that great, could've been better.

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1 year ago

My favorite place hands down. Great food and also love the popcorn. lol steak sliders are amazing and there soup is absolutely delic

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1 year ago

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2 years ago

Had a great experience! Love that they kept the popcorn tradition. Their gyro plate was very tasty and you can't go wrong the saganaki!

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Squire On The Square - sandwiches - Updated November 2026

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