Mature dating Chicago

Are you looking for singles aged 50 plus in and around Chicago? If you are looking for romance or companionship with someone local to you, you have found the ideal dating site for mature singles looking for people of a similar age.

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

Mature singles are generally looking for an easy to use website with a high level of built in security. Research shows over 40’s rarely use smartphone dating apps and over 50’s hardly at all. Both age groups have expressed an interest in using a dating site on their smartphone to browse members or read messages but are not likely to download a dedicated smartphone app to their phone.

With this in mind we ensured Generations Dating is equally accessible on any device – desktop, mobile or tablet so you can stay in touch wherever you are without the need to install annoying apps and unwanted updates.


Register for free Create your own dating profile and connect with other mature singles looking for romance.
Find matches easily Use our easy to use search facility to find compatible matches or let our state of the art system suggest members for you.
Connect with ease Chat, message or send a cheeky wink or icebreaker using our secure site or smartphone app.
Over 800,000 members Give yourself a great chance of finding someone special with one of the leading mature dating sites.

Find singles over 40 in Chicago, search for free

It's fast and free to get started. Sign up using the quick registration form above to begin. All you need is a valid email address to start browsing thousands of singles near Chicago right now.

Your personal details are kept secure and never displayed on the site. We use industry leading encryption to secure your details while Scamalytics works with our membership team to keep out scammers and time wasters.

Join free today