Illinois > Chicago > Gay Friendly Hotels Gay Friendly Hotels, current page Book Gay-Friendly Hotels in Chicago from $ Flight only Tab 1 of 3 ; Hotel only All of the best gay hotels . Feel the Pride with Your Hotel in Near South Side. Your room might be extraordinary, but you will probably want to check out Near South Side's nightspots. Many of these gay-friendly hotels can provide info on Near South Side's LGBT communities and businesses nearby. They may also be able to direct you to the gay-friendly clubs and bars. Gay Chicago: Boystown. Chicago is the nation's third largest city and boasts a large gay community. Like New York or Atlanta in their regions, Chicago serves as the Midwest's cosmopolitan hub and attracts young and old alike--all looking to escape to the freedoms and opportunities of the big city.
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