Dating for mature singles in Chicago

Generations Dating are an industry leading provider of senior dating services for over 40's. If you want to meet local singles in Chicago or anywhere in The United States looking for romance, companionship or simply looking to meet new friends, Generations Dating is the number one choice for singles over 40. With one of the biggest databases of active members in Chicago, you are sure to find someone special with Generations Dating.

Simple, fun dating for older singles

We have taken the guesswork out of choosing a dating site. If you are aged over 40 and looking for a serious relationship, a dedicated mature singles site is proven to be a more successful option.

Find someone looking for love or friendship in Chicago today

Join now for free

If you think you may have missed your chance at finding your ideal partner or new best friend, don't hesitate. Join now and start meeting new people right now.


Free to join Register for free to start dating now
Find matches easily No complicated questionnaires to complete. Let our matching system find potential matches for you
Secure communications Our secure messaging systems means you can keep your personal contact information private and store you messages in one place.
Lots of members to chose from Loads of genuine singles online every day looking for a mature partner.

Not sure mature dating is for you? You can join for free and search the site completely anonymously right away - and it's completely safe, secure and confidential with no obligations.