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Here it totally depends on where you are, and what you're looking for.
Some people have tried to put together comprehensive lists, and came up with roughly 1,800 bars operating in the city. Places that serve and cater to alcohol drinking more than food.
I did a quick search and found around 40 gay bars operating in the city.
There are 108 bars listed as late-night bars. Those are open until 4am on weekdays, and 5am on weekends. They are mostly in the north side of the city. 65 of the late-night bars are located in just the River North-Lincoln Park-Lakeview area.
The city is most known for sports bars, beer gardens and neighborhood/corner bars. The Chicago Bar Project lists over 300 active beer gardens in the city. Some areas on the north side literally have a dozen beer gardens within just a 5-10 minute walk. People visiting probably don't recognize this, as many of them are placed behind the buildings in the courtyard areas.
The city recently doubled the number of liquor licenses directly on the lakefront, and let places begin to sell hard liquor and wine. That raised a few eyebrows.
What are the bar/pub demographics in your city? Mostly men? 50-50? Young or old? Do singles go out by themselves or does everyone go out in pairs or groups of friends?
The two places I have lived most recently can't be any more opposite. In Portland, OR, people (women included) go out to bars by themselves and it isn't considered weird. Bars tend to be about 50-50 men & women (if not more women than men). And there are a range of ages, including many young people.
In Dayton, OH, hardly anyone (especially women) go out by themselves. Bar-goers tend to be majority men, and most of them are older (like 40-50+). Even the "after work" crowd tends to be this way.
I've been told it's a West vs. Midwest culture thing.
So what types of people frequent the bars where you live?
don't think it is a west/midwest culture thing...its that portland is huge for micros... and Dayton is well, I've never been but I have an idea...
chicago/milwaukee that I'm very familiar with have great "bar" culture of all types.