Overall, just take care at night – but know the most notably dangerous areas have very few (if any ) touristic attractions, so you are unlikely to end up there – even by mistake. The North Side, with Boystown and other upscale areas, is very safe but be careful of shady areas in the downtown – which empties over pretty fast after the work day is over. Although crime has declined since its peaks in the 70/80’s (linked to Al Capone’s Chicago mafia and rival gangs) mugging late at night is still stubbornly high – as is gun violence in some areas. There are some rough neighborhoods in Chicago best avoided and thieves and pickpockets do operate on the subway, so be careful with your valuables. Obviously being gay does not define which attraction most of us will want to see in each city and most queer tourists will simply want to check out the top things to see in Chicago during the day!