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

  • February 24th, 2026
  • Get Lost in My EyesGet Lost in My Eyes Hey there! I'm Hali, a fun-loving gal from Chicago, Illinois. I may not have the typical body type you see on TV, but trust me, I've got curves in all the right places. My nationality adds a little spice to my personality that you won't be able to resist. I love exploring new places and trying o...
  • Eager to Meet You in the Windy CityEager to Meet You in the Windy City Hey there! I'm Madel, a fun-loving gal from Chicago, Illinois. I may not be your typical girl next door, but I guarantee you'll have a great time with me. Whether we're grabbing deep dish pizza at Lou Malnati's, sipping cocktails at The Aviary, or strolling through Millennium Park, I'll make sure ...
  • Looking for a Fun Date in Chicago?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...
  • Latina Beauty needs love in ChicagoLatina Beauty needs love in Chicago Latina Beauty in Chicago Hola señoras. Soy Juanita y soy local en esta zona. Tengo un trabajo y tengo mi propio auto. Puedo viajar para conocerte si quieres conocerte a mitad de camino. enviarme un mensaje @Juanita4love. Tengo 5'4" y 29 años. Hello ladies. I am Juanita and ...
  • Michael 42, 5Michael 42, 5' 11 for Male Companionship in Chicago Male for Male Companionship in Chicago Not your usual male for male companion. Hey guys, I am Mike. I'm 42 and I am great at what I do.  I'm discreet and attentive to your needs. I specialize at pleasing bi-curious men. First timers welcome! I'm patient and understanding while being attentive ...
  • Chubby Chick looking for guy who can handle me!Chubby Chick looking for guy who can handle me! Chubby Looking for Dates in Chicago So, I am a little heavy but mostly just curvy. I have 44DD boobs and I love, love, love to laugh! You gotta be funny if you are going to date me. Why not message me your favorite joke and we can see how we get along!  Send your pics and contact # for mine. ...
  • Looking for the worldLooking 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, ...
  • James Bond Double wants to take you on a hot dateJames Bond Double wants to take you on a hot date Male for Male Escort in Chicago Hey, I'm Martin. You may call me Marty. I have brown hair, stunning brown eyes, 6' 4" hung and ripped. I want U to be my date. Message or text MartyHungM Kink friendly - Unrushed attention - Top or bottom - Friendly and Fun!!...
  • Looking for a Tight Pussy to Ride and Cum All OverLooking for a Tight Pussy to Ride and Cum All Over I'm a horny guy from Chicago, Illinois looking for a local woman who's down for some wild fun in the bedroom. I go by the name Mikey and you can find me on FreeSexAds.com under username mikeychi70369. I love exploring new sexual experiences and pushing boundaries, so if you're into that too, we'll...
  • Always horny. Available for fetishes 24/7Always horny. Available for fetishes 24/7 Wet Pussy Lady in Chicago, Illinois I am hot, naughty and my pussy is wet! 😈 My independent sex services include wet pussy sex with kissing, blow jobs, 🍆 anal sex, 69 and all fetishes etc. I’m always hot and ready for sex so hmu. Message me: @WetPussyLady Send your pics for mine. ...
  • LetLet's Explore Chicago Together Hey there! I'm Barney, a fun-loving guy from Chicago who is looking for someone special to share some amazing experiences with. I enjoy taking long walks along Lake Michigan, checking out the latest exhibits at the Art Institute, and trying out new restaurants in the West Loop. If you're into live...
  • Fuck Me Hard and Make Me Squirt EverywhereFuck 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...
  • Fuck me hard and make me cumFuck me hard and make me cum Are you a kinky girl who loves to suck dick, gag on cock, and get your tight ass pounded? Look no further, because I'm Ruben from Chicago and I'm looking for a local woman who's down for some wild fun. I love giving sloppy blowjobs, eating pussy until you scream with pleasure, and exploring all kind...
  • Discover Love in the Windy City with Claudius!Discover Love in the Windy City with Claudius! Hey there, fellow Chicagoans! My name is Claudius, and I'm on a quest to find that special someone who can make my heart skip a beat. 🌟 So, let me paint you a picture of what I look like. Picture this: a tall and dashing gentleman with dark hair and a charming smile that can light up any room....
  • Seeking Local Woman for Wild and Kinky FunSeeking 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...
  • Let'>Let's Explore the Windy City Together!
    Hey there, fellow Chicagoan! I'm Bay, a fun-loving guy who's ready to embark on exciting adventures with someone special. Life is too short to experience it alone, so let's create some unforgettable memories together! When I'm not busy working my day job, you can find me exploring the vibrant art...
  • WTF!  BANNED ON FACEBOOK! Wanna see the pics that got me kicked out?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 ...
  • Get Ready to Ride my Tight Ass and Suck on my Huge TittsGet Ready to Ride my Tight Ass and Suck on my Huge Titts I'm a naughty little minx from Chicago who loves to play with toys and explore all kinds of kinky fantasies. When it comes to sex, I'm not afraid to get down and dirty. My favorite positions include doggy style, reverse cowgirl, and missionary. I love getting my pussy eaten out while I moan in ple...
  • Local Librarian 📚 to let her hair down with a Chicago woman 🔥Local Librarian 📚 to let her hair down with a Chicago woman 🔥 Woman seeking woman in Chicago Hey, I'm Josephine and I am a 32 year old librarian. 📚 Even though I am not a typical-looking librarian I am pretty good at what I do and I love working around books and digital media. I am an avid reader and I love to read you a bedtime story. I must confess I lov...
  • Meet Oren: Your Chicago Date Adventure Awaits! 🌆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...
  • Fuck Me Hard and Deep in ChicagoFuck Me Hard and Deep in Chicago Are you a horny gay man looking for some hot male-on-male action? Look no further, because I'm your guy! My name is Terrel and I'm a wild stallion ready to ride your cock all night long. I can be found in the FreeSexAds.com M4M profiles under username terrelch16161. I love getting my tight ass po...
  • Get to Know Bernie from Chicago!Get to Know Bernie from Chicago! Hey there! I'm Bernie, a straight guy from the Windy City looking for someone special to hang out with. I love trying new restaurants in Wicker Park, catching a game at Wrigley Field, or grabbing coffee at one of the cute cafes in Lincoln Park. If you're into exploring the city and having fun, the...
  • Lipstick lesbian 💋 looking for lips to practice on   Lipstick lesbian 💋 looking for lips to practice on Lipstick Lesbian Loves Kissing Do you love kissing? 💋 I do! I love it!! It is such a turn on! My favorite parts to kiss are my neck and my face and my lips and my whole body! I am Kimberley, 22 and a part time waitress. I'm eager to meet you!! Send me a private message to @LipstickLesbianKim ...
  • Looking for Love in the Windy City Hey there! My name is Kelsey and I'm on the hunt for a special someone to share some amazing moments with. 🌈❤️ I'm a proud gay man living right here in Chicago, Illinois. Let me tell you a little bit about myself! Physically, I have a body that's as unique as my personality. You'll find me...
  • College Student in Chicago Need to Pay My Bills!College Student in Chicago Need to Pay My Bills! College Student in Chicago Seeking Gentleman I'm a college student with a heavy class load so I really don't have time to work a full-time job. My name is Chelsea and I'm 22 y/o. I need to pay fix my car and pay bills so I'm willing to do anything with a nice, generous gentleman. (Sorry mom!) ...
  • LetLet's Explore Chicago Together Hey there, I'm Hale from Chicago! I love exploring the city by going for long walks along Lake Michigan or checking out the latest exhibits at the Art Institute. When I'm not out and about, you can find me sipping on a craft cocktail at The Violet Hour or grabbing a bite to eat at Girl & the Goat....
  • Indulge in Passion with Renae from ChicagoIndulge in Passion with Renae from Chicago Hey there, I'm Renae from the Windy City, and I'm looking for someone special to share some unforgettable moments with. I may not be a supermodel, but my curves will definitely catch your eye. My friends describe me as fun-loving and always up for an adventure. I love exploring new places in Chi...
  • Unleash Your Wild Side with DelorisUnleash Your Wild Side with Deloris Hey there, fellow Chicagoans! I'm Deloris, your go-to gal for a thrilling and unforgettable date. Looking for someone who's not afraid to embrace their wild side? Well, you've come to the right place! Let me start by saying that I'm all about living life to the fullest. Whether it's exploring new...
  • Come Ride My Huge Throbbing Cock and Gag on My Cum, Baby!<br>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...
  • Eager to Meet You!Eager to Meet You! Hey there! I'm Lynnelle from Chicago, Illinois. I may not be your typical girl-next-door, but I guarantee you'll have a great time with me. I love exploring new places and trying out different cuisines. How about we meet up for a coffee at the trendy Intelligentsia Coffee or grab some deep-dish pizz...
  • Beauty Queen from India looking for loveBeauty 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 ...
  • Lindsey 💋💋💋 EARLY morning Sex Sessions 💋💋 SEXY MILF ❌❤ HOT MILFLindsey 💋💋💋 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 ...
  • 🌷 Absolutely A Doll 🌷 Your Perfect Asian Princess 🌷🌷🌷🌷 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...
  • Lee 28, Plumber, from UK, new to ChicagoLee 28, Plumber, from UK, new to Chicago UK Man New to the Chicago Area For Dating My name is Lee. I am from the UK and I am plumber by trade. I am looking for new people to meet in the Chicago area and I would love to meet a nice lady I can talk to and listen to and maybe more.  If you would like to say hello send me a message...
  • Male for Male Escort in Chicago. 29. 6Male 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...
  • Fuck me Hard and Make Me Squirt All Over Your CockFuck me Hard and Make Me Squirt All Over Your Cock I'm Jania, a naughty girl from Chicago who loves to get down and dirty in the bedroom. I enjoy exploring all kinds of sexual fantasies and trying out new things. Whether it's giving mind-blowing blowjobs or getting my tight pussy pounded in different positions, I'm always up for a good time. Some...
  • Looking for a Connection in the Windy City!Looking for a Connection in the Windy City! Hey there! My name is Thaxter, and I'm on the hunt for someone special here in Chicago. 🌆 I may not have the body of a Greek god, but hey, who needs that when you've got a heart of gold? 💛 I come from a mixed background, with roots from various cultures around the world. Diversity is what m...
  • Young, Free and Single in ChicagoYoung, 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 ...
  • Passionate Lesbian Seeking Orgasmic EncountersPassionate Lesbian Seeking Orgasmic Encounters Are you a lesbian or bisexual woman in Chicago looking for some hot and steamy fun? Look no further, because Harmony is here to fulfill all your wildest fantasies. I love exploring every inch of a woman's body, from sensual massages to toe-curling orgasms. I'm into everything from oral sex to an...
  • Evoke Passion with Sofia from ChicagoEvoke Passion with Sofia from Chicago Hey there! I'm Sofia, a fun-loving gal from the Windy City looking for someone special to explore all the amazing things this city has to offer. Whether it's grabbing a deep dish pizza at Lou Malnati's, strolling along the Riverwalk, or catching a show at Second City, I'm always up for an adventur...
  • Exotic Foreign Delicacy Visiting ChicagoExotic Foreign Delicacy Visiting Chicago Jasmine visiting Chicago My name is Jasmine, a foreign delicacy visiting Chicago. Poised and very classy with luscious and exotic curves. I seek to please a respectful gentleman who understands and values a high-class girl.  Send your pics for mine. Swap messages and cell numbers. @JasmineDeli...
  • Fuck Me Hard and Make Me Cum LonFuck Me Hard and Make Me Cum Lon I'm Lon, a man seeking a local woman in Chicago for some wild and unforgettable fun. I love exploring all kinds of sexual acts and fetishes with a willing partner. From giving sloppy blowjobs to receiving deepthroat gagging, I'm up for anything that brings us both pleasure. I enjoy playing with to...
  • Italian lady looking for loveItalian lady looking for love Italian lady looking for love in Chicago Ciao amore mio! Sono nel mercato per trovare un bell'uomo muscoloso e carino. Se sei carino e in forma mandami un testo per una data! (AngelicaXOXO) Hello, my love! I am in the market for finding a handsome man who is muscular and cute. If you are...
  • Sexophonist Playing your Tune in ChicagoSexophonist Playing your Tune in Chicago Male for Male in Chicago, Illinois Hey guys, my name is Milan. I play the sax and I am mixed background. I probably have a tune you like. You wanna hear me play? View my pics and message me @MellowCaramel.  I love men of all ages, races and types! Let's chat online and meet up for coffee or l...
  • Super Hot Barbie for Chicago MaleSuper 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...
  • Fuck Me Hard and Make Me Squirt All Over Your CockFuck Me Hard and Make Me Squirt All Over Your Cock I love getting down and dirty in the bedroom, exploring all kinds of naughty fantasies. My name is Roanne and I'm a wild one from Chicago, Illinois. When it comes to sex, I'm not afraid to get a little kinky. I enjoy trying out different positions like doggy style, reverse cowgirl, and 69. I lov...
  • Bosnian Beauty for Chicago GirlBosnian 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....
  • Passionate Lesbian Seeking Orgasms, Oral Sex, and Tight Ass PlayPassionate 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...
  • Fuck Me Hard and Make Me Squirt All Over ChicagoFuck Me Hard and Make Me Squirt All Over Chicago I'm a wild one, always looking for a good time in the bedroom. I love getting down and dirty, exploring all kinds of naughty fantasies. You can call me Kylen, the ultimate Chicago babe ready to play with you. When it comes to sex, I'm not shy about what I like. I enjoy giving sloppy blowjobs and ...
  • Cum Play with Madonna from ChicagoCum Play with Madonna from Chicago I'm a naughty girl who loves to suck, ride, and get fucked in all positions. My tight pussy is always wet and ready for a good pounding. I enjoy being spanked, choked, and dominated like the dirty little slut that I am. You can find me in the FreeSexAds.com profiles under username madonnachic716...