Being the third largest city in the United States, it shouldn’t be too surprising that Chicago makes the list. Time Out recently reported that 52 percent of men and 59 percent of women in Chicago are single, so your odds of running into someone who is in the same position as you are in your favor. According to the same report, 41 percent of women are even cool with “hooking up” on the first date, if it seems right (compared to only 37 percent of men). The city is also renowned for its museums, including the Art Institute and its expansive collections, including noted Impressionist works. You will never have a problem coming up with date ideas.