Meet Single Men in Chicago

Are you looking to meet someone to start a meaningful relationship with? Zoosk makes it easy for you to connect with Chicago single men to date. Online dating allows you to meet people you wouldn't usually meet in your everyday life. Take the plunge into online dating and start meeting possible people to date in Chicago. Zoosk online dating is the smart way to date!

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

Chicago Single Men

  • Picture of Edgar, 24, Male
  • Picture of Liam, 23, Male
  • Picture of Nick, 28, Male
  • Picture of fitbuffguy91, 26, Male
  • Picture of Bryce_, 26, Male
  • Picture of Adan2011, 29, Male
  • Picture of lil e, 21, Male
  • Picture of Austin, 24, Male
  • Picture of A Zoosk member, 25, Male
  • Picture of A Zoosk member, 21, Male
  • Picture of A Zoosk member, 22, Male
  • Picture of A Zoosk member, 26, Male
  • Picture of 60637, 26, Male
  • Picture of g, 25, Male
  • Picture of riley, 25, Male
  • Picture of He Pleaser', 24, Male
  • Picture of king, 25, Male
  • Picture of Freddy, 25, 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 over a bite to eat in Greektown and if all goes well, go out for cocktails or dessert..
  • Meet for drinks and appetizers in Near North Side.
  • 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.