Going to Chicago this weekend and I am trying to decide between Jilly's and the Redhead Piano Bar. Two ladies in their 40's. Any recommendations? Should we try another venue for live entertainment? Thanks for your help.

Last time I went to Redhead it was boring. They had a pretentious piano player and a singer on the side. They did requests only when they felt like it. Jilly's has a bald guy who does a lot of Sinatra. It gets pretty crowded in there- it's okay. I had a much better time at another place with this insanely crazy piano player and I can't find the name, darn it. I'm a pro piano player, so I'll give you a hint. Ask a musician where to go, not the hotel concierge!

Okay, Donna, I contacted a friend of mine who's a musician in Chicago and will get back to you. I know that the Redhead alternates entertainers, so that will make a huge difference in the atmosphere.

Thanks LLindaC - the night we will be going, the Redhead has Thomas Linsk and Lisa McClowry performing. Jilly's will have Bob Thornton. thanks for your help.

uh oh....that was the 2 I saw last time, for sure. They really were NOT playing to the crowd, IMO. I've had more fun at a sports bar. Bob Thornton is good, but he's about 80 % Sinatra, and he has a group of "regulars" who take turns singing. It's more of an ego room than a piano bar at times. I'm still waiting for my friends' response...I'l call him tomorrow if I don't hear.

Try the Green Mill. It's a blues bar, but more local.

With all due respect to the previous poster, the Green Mill is a jazz bar.

Take a look at Grape Street and Vine on E. Ontario, a couple of blocks east of N. Michigan.

We have decided to have dinner at the Chicago Chop House and it looks like Grape and Vine are just down the street. I will stear clear of the Redhead. Thanks for the help.

I've been to Davenport's once and had a really nice time. The location is a little west on Chicago avenue, but it's a cheap cab ride.

Maybe other Fodorites can offer their insights/experiences???

http://davenportspianobar.com/