Local Self Employed Singles, Self Employed Online Dating

Interested in singles who own their own businesses? Match.com has thousands of self-employed singles in Chicago, Illinois. Create your FREE profile today and start connecting!

Already a Match.com member? Sign in >>

moneynpleasure

Active over 3 weeks

moneynpleasure is single in Chicago, IL, US 2 more photos
I do love to go out, only with my fiance to places for dining, house-parties, movies, walking in the afternoon, weekend outing, etc. …

Ok, I am a male. I am 33 years old. I have never been married before. I did had one (1) past time relationship, we have been together for almost four (4) years, then she was over powered by her famili...

889187

Active within 24 hours

889187 is single in Chicago, IL, US 12 more photos
Ready to go! …

I'm on here to expose myself to a broader array of women in an effort to find the right one. I've had a blessed life so far and I'd like to spend the rest of it with a woman that I really trust and fe...

jpablo136

Active within 24 hours

jpablo136 is single in Chicago, IL, US 1 more photo
Read my profile before sending an e-mail. …

I am very demanding when it comes to the looks of the person I date or go out with. I am more than confident and very comfortable in my own skin. I am a good man at heart, and very sincere. Tall with ...

looking4theones

Active within 24 hours

looking4theones is single in Chicago, IL, US 8 more photos
Please save me from my self …

UPDATE I am on my 3rd week here and I feel the need to share some experiences with you. I can not understand why people are on a dating website to meet people and they don't reply to an email. Maybe ...

category5ive

Active within 24 hours

category5ive is single in Chicago, IL, US 9 more photos
This can't hurt right? …

I am a pretty normal person. Just busy with work and travel and family. I am very close with my parents. Thought I'd give this a whirl, since the bars become a joke trying to meet people. Looking for ...

seasonschange08

Active within 24 hours

seasonschange08 is single in Chicago, IL, US 1 more photo
The best seasons are about to come and we should be spending them together. …

Crunch, crunch, crunch, that is the sound under our feet as we run through the leaves. Yes, its fall and the holidays are a whisper away. I know my way around the city and this time of year there are ...

ccp1300

Active within 24 hours

ccp1300 is single in Chicago, IL, US 1 more photo
"Once bitten, twice shy" …

The quick version is that my career is pretty important to me, so I work a lot. I spend a lot of my free time with family, friends or playing/watching sports. I travel quite a bit but there are still ...

spininc

Active within 24 hours

spininc is single in Chicago, IL, US 5 more photos
Ready to live?? I am!!! …

Fun and relaxed. I want to find someone who enjoys exercising, would be nice to do it together but as long as we both stay healthy i don't care. I enjoy going out with friends but not every day. like ...

dock2828

Active within 24 hours

dock2828 is single in Chicago, IL, US 6 more photos
Ask yourself..."What do I have to lose?" You maybe surprised to know there are still smart & decent guys out here! …

It's usually hard to describe what your looking for so I'll take a different approach. I'm turn off by women who need to be the center of attention. Women who are too into themselves to take someone e...

sweetface7577

Active within 24 hours

sweetface7577 is single in Chicago, IL, US 3 more photos
Are you the one? …

I am an independent, self-motivated, and discipline guy who loves life and wants to get the most out of it. I believe that life is for sharing, laughing, and giving, and not for whining and complainin...

rinnaboom

Active within 24 hours

rinnaboom is single in Chicago, IL, US 6 more photos
If I like you, I'll blush. …

I'm just little ol' me- independent, quirky, down to earth, shy at first, naive, adventurous, impulsive, hands-on, tough but cute. One bad trait of mine is that I'm a little self absorbed, but it help...

Erocka84

Active within 2 weeks

Erocka84 is single in Chicago, IL, US 10 more photos
If you find yourself in a hole, stop digging. …

I'm spontaneous and I procrastinate, but I eventually get things done. I like riding around the city on my 1974 blue Schwinn. I enjoy dive bars, eating at obscure places, sleeping late on the weekends...

Cath1452

Active within 2 weeks

Cath1452 is single in Chicago, IL, US 5 more photos
Fakt jo? …

I am independent, adventurous, and sarcastic. I am always seeking new adventures, and attracted to men who are as well. I don't take myself too seriously and am extremely turned off by men (and people...

rina34661

Active within 24 hours

rina34661 is single in Chicago, IL, US 6 more photos
Write silly headline here…

Interested in meeting that rare type of man who is intelligent but not full of himself, kind but not a pushover, with a great deal of integrity. A sense of humor is critical. I like a man who can make...

DeweyButterflies

Active within 2 weeks

DeweyButterflies is single in Chicago, IL, US 12 more photos
Hopeless romantic looking for my one true love. …

I am a hopeless romantic who believes in fate, true love and love at first sight. I am an intelligent, huge-hearted person who loves people, life and everything that comes along with it. I try to give...

puellaingenua

Active within 3 weeks

puellaingenua is single in Chicago, IL, US 7 more photos
All damsel, little distress. …

I get up in the morning, make a cup of tea, have breakfast if time allows, and get ready for wherever that day is going to take me. I am, at some deep biological level, a dancer. (Irish, most speci...

bohemianartcutie

Active within 3 weeks

bohemianartcutie is single in Chicago, IL, US 2 more photos
Young Unconventional Bohemian Artist who is Independent, Intelligent, but an Old Soul. …

I am an independent person. I need space and time to do my work. I cant always be tied up in a relationship with someone, though I am loyal and always available to those I love. I am happy working 14 ...

ginade72

Active over 3 weeks

ginade72 is single in Chicago, IL, US 11 more photos
"He-he-hello"…

Hmmm...what to write what to write!! For starters I am a fun easy going person who likes to meet new and interesting people. Life is way too short to not have the best time with it. I thought this wou...

skunkbaby

Active within 3 weeks

skunkbaby is single in Chicago, IL, US 23 more photos
Pick me! Pick Me! …

Describe myself huh? I think this is the WORST part of this whole thing.. obviously im gonna sit here and tell you I'm amazingly fabulous.. perfect body.. flawless pesonality.. not one fault.. the bes...

southernbell2I

Active over 3 weeks

southernbell2I is single in Chicago, IL, US 5 more photos
“I try to believe like I believed when I was five... when your heart tells you everything you need to know.” …

I am pure through and through and know who I am. I love to be active indoors from watching movies on a rainy day, enjoying a great cup of coffee on a lazy Sunday morning to getting out for a run on a ...






 & 





Send me photos of compatible matches, tips, announcements, and special offers from Match.com and select third parties.


I am at least 18 years old and have read and agree to Match.com's terms of use and privacy policy.

View All Communities

View All Cities