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

November 15th, 2025

Passionate Lesbian Seeks Tight Ass for Orgasms and Oral Play
I'm Shena, a hot and horny lesbian from Chicago looking for a local woman who's ready to get down and dirty with me. I love exploring all kinds of kinky fetishes and sexual acts with other lesbian and bisexual women. From sensual oral sex to intense ass play, I'm always up for some fun in the bedr...

A Date with Chase: Let's Explore Chicago Together! 🌆 Hey there, fellow Chicagoans! My name is Chase, and I'm on the lookout for someone special to join me in exploring this amazing city. Whether you're a local or new to the Windy City, let's embark on an unforgettable adventure together! I believe the best way to get to know each other is by experi...

Handsome, tall and tanned guy wants to meet shy woman in Chicago Handsome Guy for Shy Gal in Chicago Male, 34 looking for gal, 26+ age. I'm a bit on the shy side so if you are also that's a plus. I warm up once I start to feel comfortable. Want a mature woman for fun, laughter and more. Message @TallEric34m in Chicago....

Fuck me hard and make me scream for more
Chryste from Chicago wants to play dirty I'm a naughty girl looking for some hot and steamy fun in the Windy City. I love getting down and dirty, exploring all kinds of kinky fantasies. From rough sex to sensual massages, I'm up for anything that will leave us both satisfied. When it comes to sex, I enjoy being on top, riding you like t...

💋 I'M Available for Local Hookup 💋 Available For Hookup in Chicago Hi! I'm Lexy. Contact me if you're ready for total sexual fun! I have been working hard and now I'm ready to let off some steam and have fun. 💗 I'm Discreet and very clean , 🚿 I CAN PROMISE U THAT I'll Treat you Like A KING👑 and I hope to be treated like a ...

Ready for an Unforgettable Adventure? Hey there! I'm Sharron, a fun-loving gal from the beautiful city of Chicago, Illinois. Looking to meet someone special and embark on a thrilling dating journey? Well, you've come to the right place! Let me tell you a little bit about myself. I have a zest for life that's contagious, and my friend...

Tall, fit Butch... Butch for Femme in Chicago Butch for Femme in Chicago. I've been single too long and would love some intimate female company. Not sure about how this is supposed to go, so here I am just saying I am looking for a date. I am romantic and thoughtful and I will bring you your favorite flowers and take...

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...

Erotic Adventures Await with Lianne79578 Hey there! I'm Lianne from Chicago, Illinois. I have long brown hair, piercing blue eyes, and a smile that can light up a room. What I love most about being lesbian is the deep connection and understanding that comes with dating another woman. I'm looking to meet a lovely lady for some fun and ex...

Looking for a Fun Date in Chicago? Hey there! I'm Derick, a straight guy from Chicago looking to meet someone special. I love exploring the city and trying new restaurants like Lou Malnati's for some deep dish pizza or grabbing a coffee at Intelligentsia Coffee. If you're into museums, we could check out the Art Institute of Chicag...

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...

I'm Alexis & I'm Everything Ur Looking 4! Alexis in Chicago: Everything You're Looking For! Hi..... I'm Alexis, a new but independent and experienced escort/provider in Chicago! I'm Looking to meet some new people and hopefully repeat clients. I am a laid back and open-minded professional lady, but I have a wild side. I will leave you smi...

Bosnian Beauty for Chicago Girl Bosnian Beauty for Woman in Chicago Hello. I am Lulu and I am 27 years of age. I speak fluent English and I now live in Chicago. I am able to travel within a reasonable distance to meet the woman of my dreams. Please send me a message @LuluLynn27 to swap photos and chat....

Fuck My Tight Ass and Make Me Gag on Your Huge Cock Are you a horny gay man looking for some hot male-on-male action? Well, look no further because I'm Gordon from Chicago, Illinois, and I'm ready to play! I love getting my ass pounded hard and deep, feeling your throbbing cock slide in and out of me. I also enjoy giving sloppy blowjobs, sucking o...

Elegantly Seductive Romy Looking for a Sweet Date Hey there! I'm Romy from Chicago, Illinois. I may not be your typical girl next door, but I guarantee you won't be able to take your eyes off me. If you're into spontaneous adventures and deep conversations over a glass of wine, then we'll get along just fine. You can check out my pics at my perso...

Let's Explore Chicago Together Hey there, I'm Woodie from Chicago! I love exploring the city by going on long walks along Lake Michigan or checking out the latest exhibit at the Art Institute. If you're into trying new restaurants, we could grab a bite at Lou Malnati's for some deep dish pizza or head to The Violet Hour for cra...

Italian/American Gigolo to make you feel good Italian Stud for Woman in Chicago Hi, I'm Alex, an Italian man, age 34, in Chicago. Italians really are the best lovers and we know what to do to please our ladies. I am an independent escort who can serenade you, cook you a beautiful meal in your own kitchen and spend the evening with you until yo...

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 ...

A Night of Passion Awaits in the Windy City Hey there, I'm Carmine from Chicago, Illinois, and I'm on the lookout for a special someone to share some memorable moments with. When I'm not busy working in the city, you can find me exploring the local art scene or catching a Cubs game at Wrigley Field. I love trying out new restaurants in Boys...

Passionate Lesbian Seeking Orgasms, Oral Sex, and Tight Ass Play I'm Beverlie, a naughty lesbian from Chicago looking for a local woman who loves to have fun in the bedroom. I enjoy exploring all kinds of sexual acts with other lesbian and bisexual women. From passionate kissing to mind-blowing orgasms, I want to experience it all with you. I love oral sex, bo...

Looking for a Connection in the Windy City!
Hey there! My name is Renaud, and I'm on the hunt for someone special here in Chicago, Illinois. 🌆 I may not have the body of a Greek god, but trust me, I've got a personality that will make you swoon! 💪🏼 And let's be real, who needs six-pack abs when you can have six-pack laughter? 😄...

Unleash Your Wild Side with Theresa from Chicago Hey there! I'm Theresa, a fun-loving gal from the Windy City looking to spice up my love life. I may not be a supermodel, but I've got curves in all the right places and a smile that can light up a room. If you're into trying new things and exploring the city, then I'm your girl! I love checking ...

Lindsey 💋💋💋 EARLY morning Sex Sessions 💋💋 SEXY MILF ❌❤ HOT MILF HOT MILF FOR EARLY MORNING SESSIONS 💋💋  Have you ever felt a sensation that makes your whole body shudder? Would you like to experience this feeling again and again? Me too!! Touch is the most incredible gift you can give or receive from someone. You need it, and I need it too, come and ...

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...

Looking for a Connection in the Windy City 💨 Hey there, fellow Chicagoans! My name is Tymothy, 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 laugh and have a good time. I may not have six-pack abs or be super tall, but my wa...

Attractive 48 yr old for younger man in Chicago, Illinois Older Woman for Younger Man in Chicago Hi, my name is Brandy, age 48, fit and attractive. I am willing to travel for the right guy but I prefer within 50 miles of the Chicago area. I am blonde (Yes, natural!) and I am cute, with a small frame and long legs. I love music and dancing and sex! Hit me ...

Tempting Tales with Forbes Hey there! I'm Forbes, a fun-loving guy from Chicago who's looking to meet someone special for some exciting adventures. When I'm not working, you can find me exploring the city's vibrant art scene or catching a live show at one of our many theaters. I also enjoy trying out new restaurants and sip...

W4W - Artistic Soul Looking for a museum-hopping companion W4W Art Lover in Omaha Username: @ArtisticSoulAge: 25Gender: FemaleSeeking: FemalePhotos: 29Videos: 2Text: Yes I'm a 25 year old woman living near downtown Omaha. I enjoy visiting the Joslyn Art Museum and wandering through the galleries at the Bemis Center for Contemporary Arts. If you're an art ...

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...

Male for Male: I can please you here or at your home. [Male for Male] Bradley M4M Escort in Chicago Area Hey guys, M4M escort in the Chicago area. I am Bradley, 31, fit, European by birth and waiting for you to call me so I can show you a great time. 5' 10" and 8 inches. View my online profile and message me BradleyKM4M. Send your photo for mine.  No hard ...

Hot Chicago guy waiting for girl of my dreams Black Man in Chicago for Romantic Woman Dark cholocate man with romantic nature. My name is Dwayne and am 6 feet 3 and well-built. I am into sports and I love watching football. Life is good and all but I want to meet a beautiful woman for passion and adventure. Check out my profile @DwayneS...

Fuck Me Hard and Deep - Spenser Are you a horny gay man looking for some hot male-on-male action in Chicago? Well, look no further because I'm your guy! My name is Spenser and I'm a kinky dude who loves to suck cock, get my tight ass pounded, and explore all kinds of wild fetishes. 🍆👅💦 I'm into everything from sloppy b...

Let's Get Lost in the Windy City Together Hey there! I'm Adelle, a fun-loving gal from Chicago, Illinois. I may not be your typical girl next door, but I guarantee you won't be able to resist my charm. Whether we're grabbing deep dish pizza at Lou Malnati's or sipping on craft cocktails at The Aviary, I know we'll have a great time togeth...

Brandon the Stud for Sex on the Side Male for Male in Chicago, Illinois Hi guys. I'm Brandon. I work out regularly and take good care of my body. I'm active and STD free. Looking for M4M fun. I do stripping, lap dances and offer full service to make you feel good all over. Top or bottom. 9" cut. Hot bod.  Check out my featured C...

WTF! BANNED ON FACEBOOK! Wanna see the pics that got me kicked out? Banned on Facebook... again! Hey there. I'm Kimberly from Chicago. My profile is in Facebook jail for posting my hot pictures. WTF?! So here I am. Want to see the pics that got me kicked out? Look me up: @KimberlyX69 My pics and videos are free. No need to pay for anything. Just look at ...

Passionate Lesbian Seeks Orgasms, Oral Sex, and Tight Ass Play I'm Rayna from Chicago, and I'm looking for a local lesbian, bisexual or bi-curious woman who wants to have some hot and steamy fun with me. I love exploring all kinds of sexual acts and fetishes with another woman. From passionate kissing to intense orgasms, I want to experience it all with you....

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 ...

Let's Explore the Windy City Together Hey there, I'm Wesley from Chicago, Illinois. I'm a fun-loving guy who enjoys exploring all that this city has to offer. Whether it's checking out the latest exhibit at the Art Institute or grabbing a slice of deep dish pizza at Lou Malnati's, I'm always up for an adventure. I'm looking for some...

Fuck Me Hard and Make Me Squirt All Over Your Cock I'm a naughty little minx named Dorri from Chicago, Illinois who loves to get down and dirty in the bedroom. When it comes to sex, I'm all about exploring new things and pushing boundaries. I enjoy giving sloppy blowjobs, riding a thick cock until I cum, and getting my tight asshole pounded from b...

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...

Get Lost in the Windy City with Me Hey there, I'm Karel from Chicago! I may not be your typical girl-next-door, but I guarantee you won't be able to resist my charm. Whether we're grabbing deep dish pizza at Lou Malnati's, catching a show at The Second City, or taking a stroll along the Lakefront Trail, I promise we'll have a great...

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...

34 years old Man seeking Woman in Chicago Man seeking Woman in Chicago, Illinois Hi there ladies, I'm Brandon, age 34, 6' tall, 220 lbs,. I am excited to meet a sexy woman who would like to explore greater depths of passion. If you would like to say hi, come and see my profile @Brandon34M and message me for pics and contact info.  xo...

Eager to Meet You Hey there! My name is Noami and I'm a fun-loving gal from Chicago, Illinois. I may not be a supermodel, but I've got curves in all the right places 😉. I'm looking for someone who can make me laugh and show me a good time. I love trying new restaurants, so how about we grab some deep dish pizz...

Get Lost in Love with Murial from Chicago! Hey there! I'm Murial, a fun-loving gal from the Windy City looking to meet someone special. I may not be a supermodel, but my curves will definitely catch your eye. I'm a mix of Italian and Irish, so you know I've got that fiery passion and luck of the Irish on my side 😉 I love exploring new ...

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...

Ken, 42, lonely for female in Chicago Male age 42 for Female Chicago Hi there! My name is Ken and I am 42 years old and looking for a real nice woman in the Chicago area. Send me a message and check my profile @Ken42seeksWoman for my recent pictures and contact info....

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...

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...

Looking for an Exciting Adventure? Let's Connect! Hey there! My name is Ericha, and I'm a fun-loving gal from the beautiful city of Chicago, Illinois. 🌆 I wanted to take a moment to tell you a little bit about myself and see if we might hit it off. When it comes to appearances, let's just say I have curves in all the right places. 😉 My fri...