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Welcome to CasualMeetupz.com, your go-to platform for finding casual hookups in Chicago, Illinois! If you're tired of swiping endlessly on apps like Tinder, you've come to the right place. Our site connects you with like-minded individuals seeking thrilling encounters and fun experiences. Chicago's vibrant nightlife and diverse social scene provide countless opportunities to meet hot contacts who share your passion for spontaneous adventures. From lively bars in Wicker Park to intimate lounges in River North, you can explore the city while making exciting connections.

Whether you're a local or just visiting, Chicago offers the perfect backdrop for your casual rendezvous. With its beautiful parks, stunning waterfront, and bustling entertainment districts, you'll never run out of places to meet sexy singles looking for some fun. Join CasualMeetupz.com today and dive into the exhilarating world of casual dating in the Windy City. Don’t let boredom hold you back—experience the thrill of meeting hot contacts in a city that knows how to have a good time!

A selection of our members looking for casual hookups near Chicago

King c3's profile picture

King c3, 49

Chicago, Illinois, USA

Looking for a friend to kick back and chill with

I’ll describe myself as a laid-back, relaxed person looking for my person

Interests: Clubs, Parties & Socials, BBW / BHM, Hookups, Friends With Benefits, A Relationship, Erotic Fiction, BBW Lover, Casual Dating, Open to Anything!

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SympatheticPrincess's profile picture

SympatheticPrincess, 24

Chicago, Illinois, USA

I’m Nat Nat but you can call me natty baby

I’m Nathaniella but you can call me Nat. I’m 24 years old, living in the Australia Plains region. I’m interested in meeting a man aged between 18 and 70. Let’s text for any kind of fun.

Interests: Anal Sex, Full Swap, Threesomes, Fetish, Hookups, Group Meets, Webcam, A Relationship, Friendship, BDSM, Casual Dating

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Maureen's profile picture

Maureen, 48

Chicago, Illinois, USA

I believe the key to a successful relationship is to love with all your heart.

I want a real man to love me for real love ... I want a man that we can both trust each other and love each other Build our own family and Grow Older in TRUE LOVE FOREVER. I treat my man like a King of the world ...I cherish and spoil him with lot of LOVE... I make him smile and happy always ... I just got hurt too much I want to find someone to trust and love unconditionally.

Interests: Masturbation, Sex Toys, Sexual Massage, Lace, Roleplay, Fetish, S&M, Dom, Sub, Hookups, Friends With Benefits, Webcam, A Relationship, BDSM, Outdoor Fun, Erotic Fiction, Lingerie, Mature, Casual Dating, Anal, Curves, Dirty Talk, Feet, Impact Play, Oral, Sex Games, Sex Talk, Open to Anything!

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Aztecpoet's profile picture

Aztecpoet, 43

Chicago, Illinois, USA

Looking for more passion in life and do build relationships.

Looking for more passion and seeking to grow relationships.

Interests: Threesomes, Discreet Meets, Hookups, Group Meets, Friends With Benefits, Friendship, Couples, Casual Dating, Swinging

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dmasck's profile picture

dmasck, 48

Chicago, Illinois, USA

submissive for Your desires! Please permit me to prove how sincere i am.

I possess a lifetime of experience on BOTH sides of the cane! Though I have always preferred the more submissive role, I have more often been required to play the Dominant, often due to a lack of satisfying experiences with Female and TS Dominants. I am not interested in 'pro-Dominants' experiences. I am currently drawn only to personal lifestyle encounters leading hopefully to a more regular, long term, arrangement or better still, a long term devoted relationship.

Interests: Sex Toys, Dominatrix, Sexual Massage, Latex, Bondage & Discipline, Spanking / Whipping, Fetish, S&M, Dom, Medical Play, Dungeon Parties, Exhibitionism, Hookups, Group Meets, Friends With Benefits, A Relationship, BDSM, Romance, Switch, gags, Pegging

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Lyra1313's profile picture

Lyra1313, 37

Chicago, Illinois, USA

Looking for My Last First Kiss 💋

I'm a book-loving, brunch-obsessed woman who loves spontaneous road trips and deep conversations. Big fan of dogs, iced coffee, and witty banter.) Looking For: (e.g. A kind, emotionally intelligent guy who can make me laugh, challenge me, and maybe dance with me in the kitchen.) Fun Facts / Bonus Points if You: (e.g. Can recommend a great podcast, love the ocean, or aren't afraid to be a little silly.)

Interests: Sex Toys, Sexual Massage, BBW / BHM, Hookups, Friends With Benefits, A Relationship, Friendship, Outdoor Fun, Couples, Mature, Casual Dating, Body Hair, Dirty Talk, Feet, Oral

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Hannah's profile picture

Hannah, 39

Chicago, Illinois, USA

I'm a trans girl available for hookup and BDSM

I'm a trans girl available for hookup and BDSM.

Interests: Sex Toys, Latex, Cuckold, Bondage & Discipline, Roleplay, Fetish, S&M, Dom, Medical Play, Dungeon Parties, BDSM, Erotic Fiction, Foot Fetish, Pony Play, Breast Play, Chasity, Contract, Electro-Play, Wax Play, gags, suspenders, Pegging

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Consid099's profile picture

Consid099, 44

Chicago, Illinois, USA

I'm looking for a real serious sub who's ready to serve and worship at my feet not here for games

That's serious sub who's ready for a fetish lifestyle

Interests: Oral Sex, Anal Sex, Sex Toys, Group Sex, Voyeurism, Sexual Massage, Soft Swap, Full Swap, Clubs, Parties, Threesomes, Cuckold, Roleplay, Dom, Sub, BBW / BHM, BDSM, Outdoor Fun, Erotic Fiction, Couples, FFF, MMM, MFM, FMF, Bondage, LGBTQIA+

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Dom's profile picture

Dom, 49

Chicago, Illinois, USA

I'm a dom female looking for my sub who is open to new things.

I'm looking for that sub that loves to be pegged. I'm looking for a sub who lives to role play.

Interests: Sex Toys, Roleplay, Spanking / Whipping, Dom, Pegging

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Trexchi 's profile picture

Trexchi , 59

Chicago, Illinois, USA

The plays the thing Let's explore our limits

I'm new to the BDSM scene. Who.will help me explore?

Interests: Bondage & Discipline, Spanking / Whipping, Fetish, S&M, Medical Play, BDSM, Switch

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PrincessBby's profile picture

PrincessBby, 35

Chicago, Illinois, USA

My Daddy and I want a third to play with 👭🏾🥰

Teasing, bdsm, watching and being watched, cuddling

Interests: Anal Sex, Hookups, Friends With Benefits, A Relationship, Casual Dating

Join Casual Meetupz to message PrincessBby

Hot ass's profile picture

Hot ass, 27

Chicago, Illinois, USA

DM to shine and explore your wildest kink with me

Describe myself as amazing beautiful and stunning 🥰😘

Interests: Clubs, Parties & Socials, Latex, Lace, Satin, Underwear, Pantyhose, Cleavage Enhancement, Padding, Female Masking, Sissy, Petticoating Roleplay, Roleplay, Exhibitionism, Discreet Meets, Hookups, Group Meets, Friends With Benefits, Webcam, A Relationship, Online, Friendship, BDSM, Lingerie, Part Time, Admirer, en Femme, en Drab, Full Time, Stealth, Transfan, Queer, Crossdress, Trans, Casual Dating, Anal, Body Hair, Bondage, Leather / Latex, LGBTQIA+, Nylons, Sex Talk, Open to Anything!

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Ts kamylla's profile picture

Ts kamylla, 35

Chicago, Illinois, USA

I am a trans woman, Disciplinarian and bondage mistress.

A dominant trans lady who’s demanding, intolerant and sometimes I can be an utter bitch. Don’t come to me with false desires. Once you click you’re hooked.

Interests: Sex Toys, Fisting, Latex, Cuckold, Bondage & Discipline, Roleplay, Spanking / Whipping, Fetish, S&M, Dom, CBT, Medical Play, Dungeon Parties, BDSM, Erotic Fiction, Foot Fetish, Trampling, Pony Play, Breast Play, Chasity, Collaring, Contract, Electro-Play, Wax Play, gags, suspenders, Pegging, Findom

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mmurr4220's profile picture

mmurr4220, 59

Chicago, Illinois, USA

Always been controlling in life but submissive in my dreams

Never followed through But ready to explore, make my dreams come true

Interests: Sex Toys, Sexual Massage, Bondage & Discipline, Fetish, Sub, First Time Encounter, Hookups, Friends With Benefits, A Relationship, BDSM, Beginner, blindfold me, Pegging

Join Casual Meetupz to message mmurr4220

Suri's profile picture

Suri, 35

Chicago, Illinois, USA

My Daddy and I want a 3rd to play

I love being teased, all that bdsm stuff, I like watching and being watched.

Interests: Anal Sex, Threesomes, Fetish, Hookups, Friends With Benefits, A Relationship, BDSM, Casual Dating

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InquisitiveShark8874de's profile picture

InquisitiveShark8874de, 28

Chicago, Illinois, USA

Looking for a sub, love to have a good time and develop meaningful connections.

I’m Italian, love being active and also reading, going to concerts, anything with tequila and 🍃 friendly

Interests: Roleplay, Fetish, Dom, Switch

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normsbigb398's profile picture

normsbigb398, 34

Chicago, Illinois, USA

Hi my name is Diana I'm a Sub/Little

Not much to tell I live with family I'm a single mother and I'm looking for my daddy hopefully I can find him here

Interests: Bondage & Discipline, Spanking / Whipping, Sub, Dungeon Parties, Erotic Fiction, Romance, Collaring, gags

Join Casual Meetupz to message normsbigb398

Maya's profile picture

Maya, 30

Chicago, Illinois, USA

I'm in for all kinds of fun perhaps I'm also a good lecturer

I'm in for all kinds of fun perhaps I'm also a good lecturer

Interests: Sex Toys, Fisting, Latex, Cuckold, Bondage & Discipline, Roleplay, Spanking / Whipping, Fetish, S&M, Dom, Sub, CBT, Medical Play, Dungeon Parties, BDSM, Erotic Fiction, Foot Fetish, Switch, Trampling, Pony Play, Breast Play, Chasity, Collaring, Contract, Electro-Play, Wax Play, gags, suspenders, Pegging, Findom

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Bhob's profile picture

Bhob, 55

Chicago, Illinois, USA

Would love to find that right clean up job..

Just looking for that woman that loves a sensual clean up… leading to another climax.

Interests: Masturbation, Clubs, Parties & Socials, Threesomes, Cuckold, Roleplay, Dom, Sub, BBW / BHM, Discreet Meets, MILF, A Relationship, Couples, Mature, Casual Dating, Oral

Join Casual Meetupz to message Bhob

mrstick903's profile picture

mrstick903, 49

Chicago, Illinois, USA

Your teddy bear of love ladies!!

I'm a nice guy, looking for a nice lady. To have and to hold on too.. I have nice strong arms for u ladies to protect you. Keep u warm at night! Most importantly, a ❤ for love! If u think that sounds good , then I'm waiting to hear from u..⚘⚘⚘⚘

Interests: Threesomes, Discreet Meets, Hookups, Friends With Benefits, Casual Dating

Join Casual Meetupz to message mrstick903

Related Locations near USA, Illinois

Hookup in other towns near Chicago such as Lincolnwood , Glenview Nas , Cicero , Elmwood Park , Oak Park , Harwood Heights , Evergreen Park , Elk Grove Village , Gary , Chicago Heights today!

Looking for something a bit different?

Find Subs, Doms and switch near Chicago at BDSM Loverz

Join swinging couples in Chicago at Red Hot Swinger

Trans and crossdressing fun in Chicago at Red Hot Trans

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