Find mature singles in Chicago

Do you live or work in Chicago and want a simple way to connect with other mature singles in Chicago for fun, laughter and maybe some romance?

Generations Dating provide an online dating service exclusively for mature singles, giving you the perfect opportunity to dip your toe into the world of online dating safe in the knowledge that many of our members will be in the same time of life as you and looking for companionship with someone just like you.

We make it easy for anyone to start dating online whatever their previous online dating experience.

Fall in love again

Make something special happen today. Join a dating site especially for people just like you and see where it takes you.

Claim your free account today and see who is online right now


Register for free Create your own dating profile and connect with other mature singles looking for love and romance.
Simple matching Finding compatible members is fast and easy. Get daily suggestions
Connect via built in communications tools Our secure messaging systems means you can keep your personal contact information private
New members every day Lots of new members registering every day gives you a great chance to meet someone special

Search and browse members for free

Begin you journey today. No commitment or credit card required. Simply register for free to see for yourself how we are different to many dating sites in The United States.

Once you create your free account you will need to activate it by clicking a link in your registration email, please use a valid email address or you won’t be able to activate your account. As soon as you activate your account you will be able to search and view single men and women over 40 from all over The United States.