on d4v3's suggestion about Whiskey Sky: neat bar, kind of small (the bar area itself), awesome views. The drinks are expensive, yes, (around $12 for a martini), but that's what you come to expect in that area.

on Kman's suggestion for Redhead Piano Bar: Also an excellent suggestion. This place gets really crowded, best to start earlier, although, I'd use that as a general suggestion anywhere in the RiNo or Rush st area. This place is mostly an older crowd (30's+). The piano music is fun, entertaining.

Despite earlier comment about it being an older crowd, when my friends and I went in there a few years back, we (in our 20's) did not feel out-of-place. We mostly felt the lack of seating, heh.

Perhaps the most "tavern-like" lounge in the Loop that I have been to is the Old Timers Lounge, 75 East Lake Street at Michigan.

It is a cheap and "honest" bar.

We're meeting a friend who is in town for Lolla and staying at the Congress Plaza Hotel. After work, mid-week. My guess is that the rooftop places just north of there will be swamped, and we are looking for someplace we can talk. The bar in the hotel has terrible reviews, but I don't want to take them too far away. I was thinking Sky-Ride, but I don't know how crowded it's likely to be? Thanks in advance...

leek wrote:We're meeting a friend who is in town for Lolla and staying at the Congress Plaza Hotel. After work, mid-week. My guess is that the rooftop places just north of there will be swamped, and we are looking for someplace we can talk. The bar in the hotel has terrible reviews, but I don't want to take them too far away. I was thinking Sky-Ride, but I don't know how crowded it's likely to be? Thanks in advance...

I had to look up Sky Ride. It's now on my list of places to try!

Would Miller's Pub or Exchequer work? Plymouth Restaurant has a nice rooftop bar -- you can make a reservation. Over on South Clark Street, Sociale is nice. Villains has a great beer list but could be loud. First Draft looked intriguing when I walked by, but haven't been.

Kitty O'Shea's in the Hilton?

I've always loved the peanuts at Monk's.

I've been to 2twenty2 at 222 s Wabash next to exchequer. While the name is terrible, it was a good enough place to grab a couple drinks.

The bar inside of the Silversmith Hotel, Adamus Lounge is okay. It tends not to be crowded and they may offer Happy Hour.

10 S Wabash Ave
The Silversmith Hotel
Chicago, IL 60603
The Loop

leek wrote:We're meeting a friend who is in town for Lolla and staying at the Congress Plaza Hotel. After work, mid-week. My guess is that the rooftop places just north of there will be swamped, and we are looking for someplace we can talk. The bar in the hotel has terrible reviews, but I don't want to take them too far away. I was thinking Sky-Ride, but I don't know how crowded it's likely to be? Thanks in advance...

Sociale is good for wine and cocktails, and Villains has a great beer list. Both have tasty bar snacks, and neither is likely to be super-crowded. Nice outdoor seating at Sociale, too.

Vol. 39 in the Kimpton is an intimate cocktail lounge that takes reservations and might fit what you are looking for.

The Silversmith does have a decent happy hour; it is a frequent choice for our office's after work drinks. Sky Ride is cool and probably wouldn't be too crowded, but it is a bit divey. I love Miller's, but after work it can get crowded.

I second Vol 39 if you’re wanting an intimate, high end cocktail lounge. They made some great cocktails as well as some tasty bites, though things are not cheap! They have a whole menu of manhattans which I found to be interesting.

I also like the various bars and lounges within the Athletic Club Hotel.

Or Miller’s If you want more of a bar vibe

My Bride and I have always been partial to...

Plymouth Restaurant & Rooftop Bar
327 S Plymouth Ct, Chicago

Maybe not the best rooftop view (Harold Washington Library) or outstanding food (serviceable enough) but enjoyable and while busy we have always gotten a seat.

Drinks were good!

We like Millers too

For all the times I have mentioned it in passing on other posts here on LTHF, I had not gotten around to queuing O'Callaghan's {again; I apologize for the Yelp link ~ wait a minute, I can occlude that ~} for this.
The secret here is to stroll the south end of the 1st floor, and find the stairway to the 2nd floor bar!
Beers and beer selections are good. There's at least one craft beer on draft going for $5. {Same price as a 12-oz. bottle of {bleh} Light.}
Have not tried the food here yet. Prior visits, I had had ramen at either Slurping Turtle or Ramen-san.
The venue is open until 4:00 am (5:00 am on Saturday ~ what day is today? ). Keenly, the wi-fi is swift. (It's via Sbcglobal - not Comcast or Comcastbusiness.) To get here from Millennium Park [What? You didn't read that thread yet?], walk north on Michigan Ave. until you get to a portal to the lower level of Michigan. This has the definite advantage of keeping you out of precipitating weather, and the potential benefit of peeping a lewd act thereupon.
Get to Hubbard St. Make a left. It will be on the south side of the block between State and Dearborn Sts.
O'Callaghan's
29 W. Hubbard St.
Chicago, IL 60654