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Chicago may be better known for its wind, but it boasts a number of online dating opportunities as well. The city on the lake is home to a major national newpaper, and singles of any lifestyle can place personal ads through the Chicago Tribune. Online dating options are best pursued through major online dating sites like Match.com and AmericanSingles.com. Online alternative dating is available through sites like gaycrawler.com. Larger national sites like Date.com and AmericanSingles.com also offer alternative lifestyle dating opportunities in Chicago.