Login

Meet Single Men Over 60 in Chicago

View Singles Now
Review your matches for free
Access to advanced messaging features
Trusted site backed by Cupid Media
International Dating

/

Men

/

American

/

Illinois

/

Chicago

/

Over 60

36 - 70 of 100
John
67 • Chicago, Illinois, United States
Seeking: Female 55 - 90
Donald
61 • Chicago, Illinois, United States
Seeking: Female 45 - 70
Genuine, Ambitious, and Ready for a Meaningful Rel
I'm a caring, loyal, and hardworking man. I believe in honesty, respect, and treating people with kindness. In my free time, I enjoy learning new things, traveling, watching movies, listening to music, and having meaningful conversations. I'm ambitious and always working toward a better future, but I also know how to appreciate life's simple moments. I value family, laughter, and building a relationship based on trust, love, and mutual support. I believe that the strongest relationships begin with friendship and grow through understanding, patience, and genuine affection.
Chapita
66 • Chicago, Illinois, United States
Seeking: Female 18 - 40
Mastering Love
a bit of a loner but happy and fullfiled
James
65 • Chicago, Illinois, United States
Seeking: Female
One last ride on here.
Animal lover, a widower and a father. I live alone and i own my car and house. I am here looking for the possibility of a serious and long term relationship. I value deep, meaningful conversations and a calm, cozy evening. I’m looking for a kind hearted, honest and caring woman to share these moments with. someone to join me for museum trips or just chatting on the porch. If you appreciate the simpler, quieter things in life, I’d love to hear from you.
R.K.
63 • Chicago, Illinois, United States
Seeking: Female 18 - 36
Bj
63 • Chicago, Illinois, United States
Seeking: Female 50 - 45
Eugene
63 • Chicago, Illinois, United States
Seeking: Female 50 - 70
I value honesty, laughter, and genuine connection.
I'm Eugene, 62, originally from Michigan. I’m calm, thoughtful, and enjoy the simple things, good conversation, slow walks, peaceful mornings, and meaningful relationships. I believe age brings wisdom, but the heart stays young. I enjoy travel, nature, music, and discovering what makes people truly happy.
Kenneth Campbell
61 • Chicago, Illinois, United States
Seeking: Female 50 - 80
Chuck
68 • Chicago, Illinois, United States
Seeking: Female 40 - 60
Seeking My Best Friend
* Santa Fe, NM transplant, have been in Chicagoland 20+ years. * Love to travel - have lived / worked / studied in the Middle East, Russia, Scandinavia, Asia and Latin America. * Interests include: fishing, cooking, photography, coffee shops, foreign films, making fine jewelry, music (blues / flamenco / jazz), gardening, DIY projects, etc. * I love most animals, but esp. horses, dogs, cats. * Non-smoker / occasional drinker. No drugs of any kind. * Fairly conservative in my political / religious views. * Looking for drama-free companionship / friendship. * I am emotionally available, honest, fiercely loyal, and a good communicator. Seeking the same in my partner. * ESTJ on the Myers-Briggs personality test. * Financially responsible / employed. You should be too (; * All photos are recent, 2024 - 2025.
Mason
65 • Chicago, Illinois, United States
Seeking: Female 57 - 80
Stephen
62 • Chicago, Illinois, United States
Seeking: Female 55 - 80
I am here to meet a kind and God fearing woman
I love to spend time with my daughter and I also love nature. If I had the opportunity to met a good woman, I will never let go of her until we are together forever
steve
62 • Chicago, Illinois, United States
Seeking: Female 24 - 40
I’m married but still looking to marrying one more
I’m kind, jovial and God, fearing man.
Barry
62 • Chicago, Illinois, United States
Seeking: Female 37 - 55
Edgar
61 • Chicago, Illinois, United States
Seeking: Female 30 - 49
Edgar
Single man looking for a simple minded other half.
Paul
66 • Chicago, Illinois, United States
Seeking: Female 40 - 57
Dan
64 • Chicago, Illinois, United States
Seeking: Female 20 - 60
Estados Unidos
Will share later
jimimack
65 • Chicago, Illinois, United States
Seeking: Female 25 - 52
Good luck 🍀
Nice and calm, good sense of humor, like to cuddle
Jeff
65 • Chicago, Illinois, United States
Seeking: Female 18 - 80
When can you get here?
If I like what I see I go after it. I'm just a guy who has needs.
Carl
68 • Chicago, Illinois, United States
Seeking: Female 39 - 53
Hopeless Romantic Seeking Soul Mate
Healthy sexy middle age male business entrepreneur mature on many levels.
Albert
65 • Chicago, Illinois, United States
Seeking: Female 45 - 52
Looking for love that I can feel
Hard working
Phillip
61 • Chicago, Illinois, United States
Seeking: Female 34 - 53
Widower Seeking Companionship
Widower looking for compatible female.
Tony
61 • Chicago, Illinois, United States
Seeking: Female 34 - 53
looking for honest and loyal
self starter
Jeffrey
65 • Chicago, Illinois, United States
Seeking: Female 36 - 75
am here in search of a serious relationship
am a good listener God fearing and well educated. I don't like lies. am kind and understanding man.
Jay
68 • Chicago, Illinois, United States
Seeking: Female 26 - 34
American Man From The City Of Chicago Seeks Love
Enjoy Pic Nics, Walks in the park. Jazz music, concerts, watching television, going to church, The Piano, The Guitar, being on my iPhone, and taking my road bike around the world to ride
James
63 • Chicago, Illinois, United States
Seeking: Female 30 - 55
Looking for the woman that God designed for me!
, single and looking for a professional, with at least a Master's degree in engineering, medicine of nursing. 
jim
64 • Chicago, Illinois, United States
Seeking: Female 36 - 56
looking for a good woman
I like building things
Charles
66 • Chicago, Illinois, United States
Seeking: Female 35 - 50
In search of Marriage only
I'm a little shy, but once I'm comfortable I can share the corny, funny side of me. Honestly, loelove
Alonzo
73 • Chicago, Illinois, United States
Seeking: Female 35 - 55
Honest open-book
A relaxed personality; a loner, but never lonely
Lamonte
70 • Chicago, Illinois, United States
Seeking: Female 31 - 50
Good guy looking for a good woman
I am retired I am a good person kind sweet Sports music entertainment, reading, dining out, writer composer pop music.
Manuel
64 • Chicago, Illinois, United States
Seeking: Female 18 - 30
Cultured Romantic
I love music, fine arts, cooking and family.
Manu
63 • Chicago, Illinois, United States
Seeking: Female 40 - 58
Happiness
Hard worker loyal willing to compromise
Steve
63 • Chicago, Illinois, United States
Seeking: Female 29 - 47
Happiness and good life
A sense of humor is a must.
Khalid
99 • Chicago, Illinois, United States
Seeking: Female 29 - 41
Mr Positive
I am a very Positive Thinking,and Acting person. I have No DRAMA in my life. I treat All Women The way I want my Sister's to be treated. I am also a Man of my WORD.
Kenneth
75 • Chicago, Illinois, United States
Seeking: Female 30 - 55
I do not send money until we meet.
I am 11 years divorced. Into health and fitness. I am Certified Senior Fitness Training Coach. Starting Small Business.
Donnie
62 • Chicago, Illinois, United States
Seeking: Female 21 - 47
x
enjoy travel

Next
first
Previous
Next
last