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So I'm headed to Chicago in August. This will be a business trip so my days will be pretty much taken. I've never been there before (other than passing in the airport) and wondering what recommendations you local residence might have for sites, places to eat, good place for a cocktail. Won't have a lot of time as I'll probably be with some colleagues some of the time also.

See if you can have a cocktail at the very top of the John Hancock building. It's on Michigan Ave. and has breathtaking views of Chicago. You can take colleagues there and you can all enjoy a drink.

Why don't you provide us with things you like to do and we can make some suggestions that fall inline with what you like doing.

If you are into breakfast, have breakfast once at an Ann Sathers restaurant - try the original location on Belmont (there are several new locations now). It used to be (may still be) a rather gay crowd. Fairy godmother Ann has passed on, and is now owned by a gay politician. If you have any free time during the day (lunch?) visit the Art Institute (good collection of french impressionists) and the old library (now a "cultural center.") If you like heavy german food, eat once at Berghoff's - on Adams Street - one of the oldest restaurants - once closed, but since re-opened.
If it's hot (most likely will be in August) consider an evening boat cruise on the lake.

go to the hard rock hotel for happy hour so much fun

Wow, thanks. As for what I enjoy, because I'll be busy all day it will most likely either be dinner or a cocktail in the evening. A gay bar where I might just chat with others would be nice. I like some of the suggestions, thanks guys!

Ann Sathers is so good. Definitely go there. Don't miss Wrigley Field for a Cubs game either. The place is awesome. The top of the John Hancock is good but the bar is packed for drinks. Get a reservation in the dining room and have dinner.

As far as bars, I'd recommend Sidetracks. It's on Halsted north of Belmont. It's a video bar for guys in their thirties through their fifties. It has one of the better and nicer crowds compared to most other gay bars.

My preferred gay bar is Minibar (a touch more upscale than SideTracks).

There are a ton of great restaurants, some of my favorites:

-Girl & the Goat
-Rustic House
-Graham Elliot
-Sola
-La Scarola

Other cool bars:

-Barrelhouse Flats
-Top of the W Hotel Lakeshore
-the Bedford

Brownie sundae at Erwin. Mmmm...brownie sundae..

Thanks guys, I'll definitely check some of these out, starting with the Brownie Sundae! LOL Also, looks like the Cubs will be playing the Reds on Thursday so I might try and catch that game.

Better off seeing a white sox game if you want excitement!

Don't miss a stroll through Millenium Park (or evening performance - often free).

Montague saidBetter off seeing a white sox game if you want excitement!

Might be an option since they're at home in the beginning of the week. Or maybe both…yeah! LOL

eb925guy said

Montague saidBetter off seeing a white sox game if you want excitement!

Might be an option since they're at home in the beginning of the week. Or maybe both…yeah! LOL

well the only good thing about the Cubs for me is that that stadium is surrounded by bars or house parties with free booze! hah

I agree with muchomas, the signature room in the Hancock building is a great place. I think you should take the time and have lunch at Portillos. Definitely try Giordanos or Lou Malnatis's for pizza!!!

Mini Bar is a cool gay bar in Boystown if you're thinking of going out but as you walk down the street you'll see plenty of places.

Since you're not a native I say you try and see both a sox game and a cubs game but it sounds like you have limited time so I say just see the team chicago has thats actually good....the sox lol.

Have a great time, there is so much to do in this city