Square One

Love this place! The bartender Adam was super cute, friendly, fun and made great drinks for me. Totally would go back just to see him!

Cheese and charcuterie selection was amazing, and enjoyed the orange marmalade, homemade mustard and crusty bread/olive oil. Wide selection of wines as well. Dark, rustic and relaxing atmosphere. Restaurant was not busy, but service was still slow.

I've been here a few times... The last time was after a wedding and we had about 10 drunk people. The staff was attentive and put up with out shenanigans. They had small bites and wine on tap. I would definitely go back.

I have been to Square One a few times since moving to Chicago and have always had a great time. The service is fast and the atmosphere is well balanced because there are plenty of people, but it's not shoulder to shoulder like the bars I went to when I was younger. They have a great menu of specialty drinks which are reasonably priced. Square One has become my go to bar in the South Loop!

Just a mediocre bar. The day I went, their self-serve wine machine wasn't working, which was fine by me. I tried the seasonal cocktail, which was a spicy and sweet cocktail sweetened with agave, and had a kick from the jalapenos. It wasn't bad, but nothing amazing. Got a couple of glasses of red wine as well- the il fauno di arcanum from Toscano was pretty good! I would pass on the Cherry Cove though, even though I like most pinot noirs from Oregon. The service here is kind of off though-- ordered our wine and still didn't arrive 10 minutes later even though there were like only 10 patrons in the bar. We had to get up and check on it, which was sort of annoying. The interior isn't bad-- high ceilings, pretty spacious, and they play movies up on the big screen above the bar, which is cool. But it kind of seemed like that was a huge space that wasn't really utilized to its potential. Oh well. I guess it's worth checking out once if you're in the South Loop and don't feel like going far to get some booze, but if you want a nice lounge atmosphere, best to go elsewhere.

I was quite impressed by this classy and swanky bar in Chicago's South Loop neighborhood. Comfortable and modern seating area (with quite a few board games) and a modern, upscale bar area, for those who prefer more of a 'cozy' feeling as they enjoy a beverage. I was quite pleased, surprised, and impressed by my good time here! Public transportation and cabs are all around; paid street parking is also available, if a bit scarce.

This is the best lounge-type bar in the South Loop. It's just as perfect for low-key dates as it is for hanging out with friends. When you walk-in from Michigan Ave, you are greeted on your right by a very comfortable looking seating area featuring two linen-upholstered couches and a bench surrounding a sizable coffee table placed in front of an equally inviting fireplace. There is a TV mounted atop the fireplace for those who want to watch games and board games (ala Yatzee, Connect 4 and Sorry) on the mantle for those who like to play. The other prominent seating options are these perfectly sized window alcoves with cushions lining the bottom and sides of the frame. They are perfect for an intimate conversation with a friend or an even more intimate conversation with a "friend". There are tasteful booth seats across from each alcove so don't worry, your group of 4 or 5 will fit perfectly. The beer and wine selections are carefully and very well selected and the staff is very knowledgeable. I can't personally speak for the cocktails but I hear good things. The food is excellent though slightly pricey as you might expect from a cozy lounge and as an update for those that have visited over the years, they recently expanded their menu to include more than just fine meats & cheeses. I had a prosciutto pizza with arugula last night (for $15). It was a good size - maybe a medium at regular pizza joints - and the flavor and texture was AMAZING! Your tip of the day is to grab a copy of their weekly promo calendar. For a long time now, they've had 50% wine bottles on Tuesdays but there are some other sweet deals that may inspire a visit. For Tuesdays specifically, try to arrive before 7pm to beat the rush. There's not always a rush but when there is, a pre-7pm arrival typically beats it.