Teddy O'Brian's

This is easily my wife and my go-to bar.  Yes, it's a bit divey.  Yes, it's a bit dirty and unrefined.  But, sometimes that's exactly what you are looking for.  The staff is great and very friendly.  We had only been there a couple of times before both Dennis and Lois knew us by name as we walked through the door.  
Beware... thier mixed drinks are not for the weak.  These guys got rid of the standard 1.5oz. or 4 count pour a long time ago.  Mixed drinks will come in a pint glass and, if you are lucky, have enough mixer to color the alcohol.  There...warning is over.
Other then that... a pool table, some silver strike bowling and darts for only a quarter.  I can safely say that this is just flat out a "comfortable, neighborhood, blue collar dive bar", and no body should take that in a negative way at all.

Overall a pretty decent place in the suburbs. Have seen some great live bands here and the drinks are cheap. Also, they service is good and the people working there are very friendly. The crowd is very hit or miss though, and the bar is either fairly empty or packed with mostly kids from ages 21-24. They're are also a lot of underage kids that get in, which brings down the experience. Overall though a decent place to chill put and get a few drinks.

Awesome selection of craft beers. Even a couple on tap. We went on sunday (3/11) to grab a drink for a friends turning 21 at midnight. Whoever the bartender, mid 50's gentleman, was plenty accommodating and polite and turned me on to a new brewing company that just came around the area. defintely nothing bad to say about him. The set up and interior are pretty much a college kid diver, which doesn't surprise me since that's the main demographic to cater to in highwood, at least in the summer time.

I'm definitely willing to return on a busier night (there were only 5 others beside us) so I can see if I would give it more stars. Until then i can only comment on what i know, rather than what i have heard.