Chicago, Illinois Free Sex Ads for Local Adult Hookups
Chicago, Illinois free sex ads. Meet locals looking for sex hookups near you. It's free to search these adult classifieds, or post your own ad!
Home / Free Sex Ads /
Show Ads In: Bloomington-Normal | Carbondale | Champaign-Urbana | Chicago | Decatur | Peoria | Quad Cities, IA/IL | Rockford | Springfield, IL
September 5th, 2025
Fuck Me Hard and Deep - Vaughan's Raunchy Gay Male Ad
Looking for a hot gay man who loves to get down and dirty in the bedroom? Well, look no further because I'm your guy! My name is Vaughan and I'm a horny gay man from Chicago, Illinois who is seeking other gay, bisexual or bi-curious guys for some steamy male-on-male fun.
I love everything from s...
Fuck me hard and deep in Chicago Hey guys, I'm a horny gay man named Burt from Chicago looking for some hot male-on-male action. I love getting my tight ass pounded and sucking on a throbbing cock until it explodes in my mouth. I'm into all kinds of kinky stuff like rimming, BDSM, role play, and using toys like dildos. Let's explor...
Get Lost in the Windy City with Krissy
Hey there! I'm Krissy, a fun-loving gal from Chicago, Illinois. I may not be your typical girl next door, but I guarantee you'll have a blast hanging out with me. Whether we're grabbing deep dish pizza at Lou Malnati's, sipping cocktails at The Aviary, or catching a Cubs game at Wrigley Field, I'l...
King of your heart waiting for you in Chicago Abe, 32, local in the Chicago area, own my own business. I work hard and play hard. I am looking for a gentle guy who is understanding and kind. I love to laugh so you have to be funny. Not all the time, but you need a good sense of humor. Life is too fun to be serious all the time. Message me ...
Looking for a local woman who loves to fuck, suck, and play
I never thought I'd be writing one of these ads, but here I am. My name is Ian and I'm a man seeking a local woman in Chicago, Illinois for great sex, adventure, and fun. You can find me in the FreeSexAds.com dating profiles under username ianchic49223.
I love exploring all kinds of sexual acts a...
FB Banned Me For These Pics. WTF!! Chicago M4M Male for Male in Chicago for Pic Swaps
Hey guys, I'm Sebastian. I'm fairly new to the Chicago area. I'm interested in meeting a man for male companionship and fun. I am fit and love to show off my body. I apparently got in trouble with Facebook for posting my pics. Message me online for special acc...
Looking for a Tight and Sloppy Blowjob Queen I'm Al, a man seeking a local woman in Chicago, Illinois for some wild and raunchy fun. I love exploring all kinds of sexual acts and fetishes with the right partner. From passionate kissing to rough play, I'm open to trying new things and pushing boundaries.If you're into deepthroating, gagging, an...
Smokin' Hot and ready for a date! Hot Girl for Man in Chicago
Ok, so maybe Smokin' hot is something you need to decide, but hey, I have a sense of humor! Seriously though, I do think I am quite attractive and I have certainly been complimented often. My hair, especially, gets a lot of attention because it goes way down my back and ...
Mark, 33 Love country music and driving my truck Hey, the name is Mark and I am a country boy now living in Chicago, age 33, a mechanic and I love to drive my Dodge ram 1500 out on the open roads. Sometimes I take a blanket and a beer and hang out at my favorite lake a few miles from my house in the Chicago area. I am self sufficient and I am want...
Fuck Me Hard and Make Me Squirt Everywhere
I'm a naughty girl from Chicago who loves to get down and dirty. My name is Ida
, and I can't wait to explore all your wildest fantasies with you. When it comes to sex, I'm open-minded and always up for trying new things.
I love giving sloppy blowjobs and feeling your cock deep in my tight pussy...
Your Ultimate Erotic Experience in Chicago!! Erotic Sex Hookup in Chicago
I am very honest, sweet, and loving young woman, I am a Christian, that is my background, religious and I believe in real love, I am here looking for real love and a man that I believe I deserve, I love cooking, dancing, cleaning, watching movies, I am down to earth out...
Meet Oren: Your Chicago Date Adventure Awaits! 🌆
Hey there, I'm Oren from Chicago and I'm looking for someone special to explore the city with. Whether it's grabbing deep dish pizza at Lou Malnati's, catching a Cubs game at Wrigley Field, or strolling along the Riverwalk, I'm up for anything fun and exciting.
I love trying new things and makin...
🌷 Absolutely A Doll 🌷 Your Perfect Asian Princess 🌷🌷🌷 Sexy Asian Girl Available in Chicago
I am Choko @ChokoSexyBusty (my profile and pics), age 21. I am Asian girl Sexy Busty girl with 36D-25-35, 108 lbs, amazing body with silk smooth skin, absolutely charming stunning... Time to relax ..... Time to unwind ..... Let me pamper you let me spoil yo...
Passionate Lesbian Seeks Orgasms, Oral Sex, and Tight Ass Play
Are you a lesbian or bisexual woman in Chicago looking for some hot and steamy fun? Look no further! I'm Daisey, and I'm ready to explore all your wildest fantasies with you. From passionate kissing to mind-blowing orgasms, I love it all.
I enjoy oral sex, anal play, role-playing, bondage, and e...
Fuck Me Hard and Make Me Squirt All Over Chicago
I'm Kati, a wild girl from Chicago looking for someone to satisfy all my dirty desires. I love getting down and dirty in the bedroom, exploring new positions and kinks that will leave us both breathless.
When it comes to sex, I'm not shy about what I want. I love giving sloppy blowjobs, riding ...
Your Seductive Little Secret in Chicago Hotness69XXX - I'll be Your Seductive Little Secret in Chicago
@HOTNESS69XXX Message me for my private pics
Hi, I'm Monica, age 24. I'm ready when you are! I'm told I am fun-loving and have a beautiful smile that will brighten your day. If that doesn't work -- I give good head!
I am sexy and...
Seeking Local Woman for Wild and Kinky Fun
I'm Tristan, a guy from Chicago looking for a woman who's up for some hot and steamy action. I love everything from passionate kissing to rough sex and everything in between. I enjoy giving and receiving blowjobs, eating pussy until you cum all over my face, and fucking in every position imaginabl...
Eager to Meet You
Hey there! I'm Meggan from Chicago, Illinois. I may not know you yet, but I'm excited to change that 😉. I'm a fun-loving gal who enjoys trying new things and exploring the city. Whether it's grabbing a slice of deep-dish pizza at Lou Malnati's or taking a stroll along the Riverwalk, I'm always ...
Male for Male Escort in Chicago. 29. 6' 2 Male for Male in Chicago
Hey, I'm Jeffrey. Will visit you or you can visit me 29. 6' 2. I'm working my way through college but I manage some free time. Need to spend time with men. I love the male form and appreciate all types of men and all body types. Message @JeffOralExpert for a get togeth...
Baby Face Hot Dude waiting for the ladies Male Escort in Chicago
I am Howie and I am waiting for you. I am 37, hung and it. I focus entirely on your pleasure and will do what you want. Your satisfaction is my top priority and guaranteed! Message or call @BabyFaceHowie...
Looking for the world's best playmate! Need: One good looking guy who can make me laugh
Also: has to like music and movies and be a gamer, not a player.
What you get: Me! My name is Patrice and I am 25, 5'6", curvy with darkish brown hair with a blue streak straight down the back of my head, which I love! I am also a pretty good cook, ...
Fuck Me Hard and Make Me Squirt All Over Your Cock
I'm a naughty little minx looking for some hot and steamy fun in the Windy City. My name is Robina and I love getting down and dirty in the bedroom. Whether it's a passionate blowjob, riding your cock like a wild cowgirl, or getting my tight asshole pounded from behind, I'm always up for a good ti...
Sweet and Sensual Penelopa is Waiting for You! 💋
Hey there, I'm Penelopa, a fun-loving gal from the beautiful city of Chicago, Illinois. Looking for a special someone to share some amazing moments with? Well, look no further because I might just be your perfect match!
Let me tell you a bit about myself. Physically, I'm blessed with curves in al...
Unleash Your Wild Side with Natalee
Hey there! I'm Natalee, a fun-loving gal from the Windy City looking for someone special to share some laughs and good times with. I may not be your average girl-next-door, but I guarantee you won't be bored when you're with me.
I love exploring new places in Chicago, whether it's grabbing a dee...
Super Hot Barbie for Chicago Male Hot Barbie in Chicago, Illinois
Hello!! My name is Phoebe and my intelligence and charming personality is sure to make you feel comfortable! I am just looking for a cool guy I can date around here and have some fun together! You want to meet me? Send me a message with your pics and number! @Ho...
Eager to Meet You in Chicago! Hey there! I'm Alexia, a fun-loving gal from Chicago looking to meet someone special. I may not be your typical girl-next-door, but I promise you won't be disappointed. Let's grab a coffee at the trendy Intelligentsia Coffee or enjoy a romantic dinner at the iconic Girl & the Goat. If you're feeling...
24 y/o Bartender for No Strings Fling No Strings Fling in Chicago
Hi! I am Kimberly and I am 24! I have a loveless marriage. My job is fun and I love my customers. Some of them flirt but they are just my customers. I want to meet a sexy guy who will be kind and attentive and loving! You must be out there somewhere!
Contact me me if yo...
Fuck Me Hard and Deep in Chicago
Are you a horny gay man looking for some hot and steamy action? Well, look no further because I'm your guy! My name is Levy and I'm a wild and kinky gay man who loves to get down and dirty with other guys. I'm seeking gay, bisexual or bi-curious dudes who are ready to explore all kinds of male-on-...
Passionate Lesbian Seeking Orgasms, Oral Sex, and Tight Ass Play
I'm a wild lesbian from Chicago looking for a sexy lady to have some naughty fun with. Ilyssa here, ready to explore all your wildest fantasies. I love getting down and dirty with other lesbian and bisexual women who are as eager as I am.
When it comes to sex, I'm into everything from passionate ...
Unleash Your Inner Fire with Julianna from Chicago
Hey there, potential flame! My name is Julianna, and I'm on the hunt for someone who can handle my sizzling personality. 🔥 Living in the heart of Chicago, Illinois, I bring a unique blend of passion and excitement to every date.
Now, let's get one thing straight: I'm not your average girl-next...
Young, Free and Single in Chicago Lonely in Chicago
You have got be out there somewhere! I am lonely and I would love to find a funny and happy-go-lucky guy who can be my best friend and lover. I'm hoping you look good in a cowboy hat and jeans! View my profile and private pics @LonelyinChicago so we can at least swap pics and get ...
Divorced College Lecturer Looking for Excitement! College lecturer and divorcee, age 42, looking for someone loving, intelligent and fun. I live in the Chicago area and I am happy to meet at a neutral place or entertain at my place. I own my own home and I am not expecting you to pay for everything. Looking for someone who loves history and books, ...
Lesbian Fitness Freak with Sporty Body in Chicago Lesbian Fitness Freak in Chicago
Hi ladies! This is your girl Teri! I love to work out. I run, I lift weights and I am fit and tanned. My height is 5'8" and I have brown eyes and blonde hair. I want a woman who is her own person and financially responsible.
If you are a fun type who loves fi...
Come Ride My Huge Throbbing Cock and Gag on My Cum, Baby!
I'm a horny guy from Chicago looking for a local woman who can handle all the dirty things I have in mind. I'm Stewart, and I want to find a sexy lady who's down for some wild fun. You can find me on FreeSexAds.com under the username stewartch77522.
I love getting my dick sucked until I explode w...
Totally new to this kind of thing! Single Girl in Chicago
I use a couple of apps to do dating but I have never tried this site before. I am hoping I came to the right place. Are you my Mr. Right? I hope you are! My name is Lisette and I am 26 and single and I love to go to the beach and the movies. Check out my profile page and send...
Let's Fuck, Suck, and Play All Night Long!
I'm Rick from Chicago, Illinois, and I'm looking for a local woman who's ready for some wild and raunchy fun. I can be found on FreeSexAds.com under the username rickchic15185.
I love everything from passionate lovemaking to kinky role play. I enjoy giving and receiving blowjobs, exploring differ...Looking for a Connection in the Windy City! 🌬️
Hey there, fellow Chicagoans! My name is Bearnard and I'm on the lookout for someone special to share some amazing moments with. 🌈
So, let me tell you a bit about myself. I'm an easygoing guy who loves to embrace life's adventures. 💪🏼 Despite not being built like a bodybuilder, I've got ...
New to the Chicago, Illinois area and lonely! Lonely Woman seeking Man in Chicago
I am new here in this town and I would like to meet handsome gentleman to go to dinner and on a date with. You are interested in me please send message to me. @RagazzaSexyX
Sono nuovo qui a Chicago
Sono nuovo qui in questa città e mi piacerebbe...September 4th, 2025
Wild Chicago Bitch Ready to Ride Your Cock
I'm a naughty girl from the Windy City looking for some hot and steamy fun. You can call me Katherina, and I love to get down and dirty in the bedroom. Whether you want me to suck your cock until you explode or ride you like a wild animal, I'm game for anything.
I'm not shy about my kinks either....
Looking for a Local Woman to Ride My Huge Cock and Gag on My Throbbing Dick
I love getting down and dirty with a sexy lady who knows how to please a man. I'm Paul from Chicago, Illinois, and I'm looking for a local woman who can handle all the kinky fun I have in store. You can find me in the FreeSexAds.com dating profiles under username paulchic43163.
I enjoy everything...
Unleash Your Desires with Marsiella
Hey there! I'm Marsiella from Chicago, Illinois. Looking for someone to explore the city with? Let's grab a deep dish pizza at Lou Malnati's or take a stroll along the Riverwalk. You can check out my pics at my personal bio page @marsiellach88920. Who knows where the night might take us 😉
I'm ...
Hot and Horny Guy Seeking Local Woman for Wild Fun
Are you a naughty girl who loves to get down and dirty in the bedroom? Do you enjoy exploring your wildest fantasies with a man who knows how to please you in every way possible? Well, look no further because I am here to fulfill all your desires and more. My name is Garwin, and I am a man seeking...
Fuck Me Hard and Deep in Chicago
I'm a horny gay man looking for some hot male-on-male action. My name is Bryan and I want to find guys who are into all kinds of kinky stuff. I love sucking cock, getting my tight ass pounded, and playing with toys. If you're into rimming, gagging, or sloppy blowjobs, I'm your guy. Let's explore e...
Fuck me hard and make me squirt all over you
I'm Celie, a naughty girl from Chicago who loves to get down and dirty in the bedroom. I enjoy exploring my sexuality and trying out new things. Whether it's giving a sloppy blowjob or riding you like there's no tomorrow, I'm always up for a good time.
Some of my favorite positions include doggy...
Beauty Queen from India looking for love Beauty Queen from India Now in Chicago
My name is Manju and I came from India in 2002. I am a college graduate and I work in retail. I am looking for someone who is exciting and fun, but honest and trustworthy. If that is you please message me @ManjuChicago so we can get together. I look ...
Passionate Lesbian Seeks Orgasmic Encounters
Are you a woman who loves exploring every inch of another woman's body? Do you crave the taste of sweet, wet pussy on your lips? Well, look no further because I'm Gwennie from Chicago, Illinois, and I'm here to fulfill all your wildest fantasies.
I'm looking for a local lesbian, bisexual, or bi-c...
Still unpacking but looking for a date in Chicago New Girl in Chicago
My name is Charlene and I literally just move here last week. I have barely unpacked yet and I am so wanting to get out and meet people! I love the movies and popcorn and music and dancing and having fun! Go ahead and hit me up for a date, or a drink or something! Message m...
How do I look? / M4W in Chicago Man for Woman in Chicago
Check out my profile and tell me how I look. I am Sam. I'm a model, age 32 and told I am darn hot looking. Hit me up and check out my profile @SamChicago. Send your pics for mine. I'm available evenings and weekends.
Sorry guys, no men.
I appreciate femin...
Explore My Sensual Side with Alyson Hey there! I'm Alyson, a fun-loving gal from Chicago who's looking to meet someone special. I may not be a supermodel, but I've got curves in all the right places. My friends would describe me as adventurous, spontaneous, and always up for trying new things.
I love exploring the city and checking o...
No Strings - Hot and Sultry, Looking for Affection in Chicago No Strings Hookup in Chicago
Thanks for opening my ad. I've been neglected for far too long and am in need of affection. Things are complicated so no strings only please. That is likely to change at some point in the future.
My hair goes down to my lower back and I have soft skin. My height is 5'8...