Meet Single Men in Chicago

Are you hoping to meet a single man to commit your attention to? Zoosk is full of great single men interested in meeting new people to date. Dating online gives you the opportunity to get to know someone a little before agreeing to an initial meeting. Sign up now and start browsing pictures of Chicago single men. Date smarter. Try Zoosk online dating.

Date smarter.™ Use Zoosk to meet your next date.

Chicago Single Men

  • Picture of Marco, 24, Male
  • Picture of Sonny, 24, Male
  • Picture of A Zoosk member, 26, Male
  • Picture of chitowndesigner, 25, Male
  • Picture of emoxx, 23, Male
  • Picture of A Zoosk member, 21, Male
  • Picture of Brandon Scott, 29, Male
  • Picture of Edgar, 25, Male
  • Picture of Brian G, 28, Male
  • Picture of Dutis9, 23, Male
  • Picture of Chitownguy, 26, Male
  • Picture of Trynda, 22, Male
  • Picture of George, 25, Male
  • Picture of A Zoosk member, 28, Male
  • Picture of mansour, 21, Male
  • Picture of A Zoosk member, 27, Male
  • Picture of manny, 26, Male
  • Picture of Bplittle95, 22, Male

Chicago Date Ideas - Meeting an Online Date in Public

Use Zoosk to meet Chicago single men online, then setup a date to meet at a public place in real life, IRL! Here are a few Chi-Town date ideas:

  • Meet at a coffee house in the Loop and then, if there seems to be a spark, go pick up a slice or sit down for a pie..
  • Meet for drinks and appetizers in Near North Side.
  • Meet for pizza in Lakeview, then try bowling or a game of pool at Southport.
  • Have a beer together in Wicker Park-Bucktown area and if it feels right, continue the date with dinner.

Join Zoosk Online Dating for FREE!

Browse photos of Chicago single men, flirt with potential matches and set up a date in Chicago for tonight! Zoosk has millions of single members looking to meet new people, have fun and find that someone special.