While most LGBT people zero in on Boystown the gayborhood for accommodation, there are only a handful of hotels here. However, there is no dearth of gay lodging in Chicago and plenty of gay friendly hotels to choose from. If you’re looking for exclusively gay hotels in Chicago you may be a little disappointed as there are none. America’s ‘Windy City’ may not be high on the travel itinerary of many from the LGBT+ community given its ‘low key’ gay image, but you’ll be surprised with all that Gay Chicago has to offer.