main background cupid
Log In

Are You Looking for The Best Dating Site in Chicago?

My location
By clicking the submit button above you expressly consent to our Privacy policy including processing of personal data and use of profiling to find you matches and you agree to our Terms of use, and to receive newsletters, account updates, offers sent by Cupid
Next
Start NOW!
Tell Cupid who are you looking for?
Gender
woman
man
Age
18—29
30—39
40—60
Orientation
Traditional
bisexual
Gay
Lesbian
Check out our users to meet your love in Cupid
About Me
People inject too much drama into romance, and that's just the wrong way to go about it. I have a stoical attitude and am not easily insulted or disappointed.
New
riony
Chat
Like
About Me
I’m looking for a nice and kind man, not older than 30. I’m Nova, 25.  I love swimming, listening to music, watching movies, and petting my lovely puppy.
New
Nova Perez
Chat
Like
About Me
I’m Nora, 28. I believe that I’m a highly-sensitive girl. I’m eager to give love and hope and get involved in a long-term relationship with commitment.
New
Nora Thompson
Chat
Like
About Me
It's fair to say that I dated quite a few guys in the past and understand very well what I'm attracted to. My favourite type of man is an urban heterosexual with a good education.
New
JennJenn
Chat
Like
About Me
Hello, am Tanya, a 21-year old married woman with a big heart. I’m looking for a man who has an equally big heart for a relationship.
New
Tanya Stevens
Chat
Like
About Me
I hate the mystification of healthy relationships! It's really not all that complicated. Two people either have something to share, or they don't! Let's not overthink it.
New
SheissheilA
Chat
Like
About Me
I work hard; that's why I signed in to this website... I am looking for a man who is mature, serious, steadfast, and purposeful. I want to have a great love life.
New
 Sheila_Painter
Chat
Like
About Me
Hi, I’m Ruth, 27 years old and widowed. I need a serious man for love and relationship that can lead to marriage. I hope to find someone who loves kids like me!
New
Ruth Darling
Chat
Like
About Me
 39 years old single woman. Conservative. Reliable. Staunch Christian. I’m looking for a relatively quiet, calm man and shares in the same spiritual sense.
New
Rebecca Mathews
Chat
Like
About Me
 I’m a 39 years old single woman but still looking young and energetic. I’m here for just one man who is hilarious, romantic and can make me smile even on those dull days.
New
Kelly Meredith
Chat
Like
About Me
  I think of myself as a sassy, classy, 32 years old smart, single woman. I’m into a man who will love me back the same way I love them.
New
Wendy Jenkinson
Chat
Like
About Me
 A man who will keep surprising me with little things is what my heart is looking for.  On the other hand, you will get a loyal and most loving 30-year-old single woman to call your own.
New
Eliza Larsen
Chat
Like
About Me
 I’m 35 years old. I’m a loving single woman. I’m what your mother would want for a daughter in law. I’m looking for a real man who will make me smile for no reason.
New
Nicola Hudson
Chat
Like
About Me
 Greetings everyone. I’m 34 years old, an easy-going single woman. I’m looking for a serious man who will be why I look at my phone and smile.
New
Suzzane Holland
Chat
Like
About Me
 Hi everyone? My name is Dianna,34 years old, I’m a single woman and looking for a man who will be soul mate and who can make me smile for no reason.
New
Dianna Murphy
Chat
Like
About Me
  All that this 32-year-old single woman want is a serious and responsible man for a serious relationship that can lead to marriage 💍.
New
Lorretta Smith
Chat
Like
About Me
 I got married a year ago but life is not what I expected it to be. My husband is always critical of me and what I do. I need a man to comfort me, hold me, and tell me I’m not the problem.
New
Ruth Underwood
Chat
Like
About Me
 I’m young at heart, married at young age but full of life. I know what I like and just here seeking a man I can proudly tell my mum I’m going out to meet.
New
Tanisha Sawyer
Chat
Like
About Me
 I’m a black American woman and my husband started doing drugs because of depression. I need someone who can step up for his husband duties before everything comes back to normal.
New
Charlotte Shaw
Chat
Like
About Me
 You should message me up if you’re not allergic to nurturing some serious relationships with a married woman, crave some humor, wit and sarcasm.
New
Alice Campbell
Chat
Like
About Me
As a mother of one rater expressive child, I have learned to value the skill of understanding and listening. I need a man who is open about his feelings and will be willing to share them with me.
New
Yvonne
Chat
Like
About Me
I am a busy widow who has spent most of the last 32 years of her life working and establishing herself. I am looking for a man who can help make my home a fun ground free from all work.
New
Tara
Chat
Like
About Me
Widowed with a lovely son. I am a hard worker and want to find a gentleman who can make me laugh, relax and make some beautiful memories together. I’d love to hear from you.
New
 Joanofdark62
Chat
Like
About Me
After a difficult marriage, I really need some comfort and understanding. Is there a single gentleman out there capable of turning my sorrow into joy?
New
Betsy
Chat
Like
About Me
I work in a primary school, and dating is rarely the first thing on my mind, so I am not sure what I am looking for exactly. Maybe someone could surprise me, lol C
New
Maria
Chat
Like
About Me
I'm a pretty woman :) I want to feel the passion of a man. I want just to enjoy the fun of our relation. Are you ready for this? Welcome dear
New
Jessica
Chat
Like
About Me
It’s funny that I’m called Winter, but my favourite season is the summer. I want to spend the day on the beach with a good-looking partner with a great bod. Hopefully he is on this site!
New
WinterSnow
Chat
Like
About Me
I am an optimist; I try staying positive in any situation. I am seeking a kind person who wants to enjoy a simple life.
New
Sally
Chat
Like
About Me
Blonde hair (going grey haha) blue eyes, and a cheeky smile. Looking for Mr Darcy to sweep me off my feet.
New
LittleJane
Chat
Like
About Me
I am an adventurous and enthusiastic woman of 51 who still loves to rock climb and mountain climb. I am looking for a guy who is also in love with physical activities and is willing to go with me.
New
Violet
Chat
Like
About Me
I am looking for a person who has that same respect for animal life. I hope to find a caring man who wants the world to be kinder.
New
 Jessica
Chat
Like
About Me
Hi...When I was a young girl, I have been told I could not love someone until I love myself... It is true... I'm down earth and very thoughtful woman. I want to meet love again
New
 Melis-lov
Chat
Like
About Me
Hi! I am a pretty woman who loves life. I am a person full of love, a person of a sweet and full character. Looking for an affectionate, intelligent, mature man, that wants a relationship with me. 
New
 Jonelly
Chat
Like
About Me
Sane, solvent woman. Reluctant extrovert. No mountain peak was harmed with a yoga pose during the making of this profile.
New
Maisie May
Chat
Like
About Me
As a single 49-year-old who has established herself as a local entrepreneur, all I need is a man established in his field to be my friend/partner all the rest of my days.
New
Elizabeth
Chat
Like
About Me
As a 60-year-old mother of two and grandmother of three, I seek someone to spend the rest of my days with (✷‿✷). Simple, kind, loving, and a man of honor is all I seek in any man.
New
Ruby
Chat
Like
About Me
I'm a PR manager in a huge company, so I would like to think that I'm good with people. I can't fire you, but I can set you on fire! JK I'm cool
New
MariaHaha
Chat
Like
About Me
Make-up artist. I can make your face as beautiful as any, but ironically prefer girls without make-up.
New
Veronica28
Chat
Like
About Me
Looking for fossils under rocks will make any trip to a rocky coast an adventure. You never know what delights are hidden under that million-year-old geology. Join me unearthing Jurassic Park.
New
RarrahSarah
Chat
Like
About Me
A night of gin tasting will introduce you to some mouth-watering flavors of this refreshing spirit. With so many to choose from, I really need a companion to help me make a tasty selection.
New
atasmCharlie
Chat
Like
About Me
I’m Holley and I’m just looking for a woman that I click with. I’m into all sorts of things from board games to boozy nights out, so if you want to find out more just drop me a line.
New
Holls_32
Chat
Like
About Me
I'm as idealistic as any Libra can be. Here to find my match and spread positivity. Plump blonde covered in tattoos. Let's talk!
New
Brittany Hufstetler
Chat
Like
About Me
Fleamarkets are incredible places. I’ve spent many hours sifting through the debris searching for hidden gems. If you have a passion for unearthing mysteries, let’s get together and start our search.
New
YogytonPeyton
Chat
Like
About Me
Do you enjoy raquet sports? Tennis, table-tennis, badminto or squash? I’m into all of the above. I would love to meet a female to become a regular competitor – and romantic partner, too.
New
BubbouMaria
Chat
Like
About Me
I do believe that love is a work in progress. My friends call me practical yet romantic. I hope to find a nice lady in her 40s to become my new lover. I am sweet & attentive. Let us go on a date soon.
New
Isabella Thomas
Chat
Like
About Me
I quit my accounting job so I could travel for a living and it was life-changing. Now I'm ready to settle down with a loving partner. Interested to date a 42y.o. adventurer?
New
Milla Saccone
Chat
Like
About Me
Music is half of my life and I want you for the other half! 55, 1 daughter. Kids fine! I’m not picky but I don’t like to message first!
New
MusicalLilly
Chat
Like
About Me
Let me show you how a woman can truly love & care for another woman. My passions are genuine & my heart is pure. I’m looking for a lover who can cope with my delicious insanity. We will have utter fun.
New
Amber Lewis
Chat
Like
About Me
Lovelynova: Starbucks coffee, romantic movies, swimming, Friday night out. Maybe if you can relate to any of these, we can hang out sometime. Anyone?
New
Nova Gibbs
Chat
Like
About Me
PrincessZhavi: True love is patience, requires sacrifice and total commitment. I might be 20 years old bisexual lady, but that what I'm here for. If you are serious and committed, let's talk.
New
Zhavi Dixon
Chat
Like
About Me
Galleries can put you in touch with so many marvelous examples of art, from Rennaisance masterpieces to pop art, sculptures to slideshows. I'm looking to date someone else who appreciates art.
New
Claire
Chat
Like
About Me
If you can’t stand a feisty, strong willed woman, we won’t have any conversation now, and definitely nothing going forward. I need a woman in my life that can handle my strong-willed personality.
New
FillMeUp
Chat
Like
About Me
I’m getting a little fed up with the constant distraction of social media. My phone and laptop are always enticing me to check on the latest posts. I need a distraction. The more physical the better.
New
Alexandra
Chat
Like
About Me
I must admit I like to have the occasional night out at a casino. My favorite game has got to be roulette. What are the odds you and I might hit it off? Why not gamble on hitting the jackpot?
New
Reagan
Chat
Like
About Me
I love steam train journeys. There’s something so romantic about those wonderful locomotives and their glamorous passengers. Let’s you and I book a trip to a distant railway station.
New
Holly
Chat
Like
About Me
I’m of age, and have come to know more about myself than ever. I’m confident being bisexual, and would like to engage a lady for serious chats, hoping to put a ring on her finger someday.
New
FleetingLove
Chat
Like
About Me
Single, outgoing, and friendly woman looking for a man or woman for a romantic relationship.
New
ElleBelle
Chat
Like
About Me
I’m a lover of all things health – but I’m not a doctor, not even a nurse, dreamt of being a fitness instructor, and didn’t happen. So, I’m looking for a young man to remind me of the good old days.
New
Juliana Dionne
Chat
Like
About Me
It’s never what it seems, or so I’ve learned dating men over the past two decades. That said, I’d like a woman experienced in dating other women, and is now ready to settle down, like I am
New
Anastasia Jackson
Chat
Like
About Me
I’m the quiet girl in the room, who happens to get loud when the need arises on that note, I’m looking for someone to bring out the real me, for years to come, preferably a bi-lady in my area.
New
Vera Clark
Chat
Like
About Me
 Would like to meet another bowling fan. I’m always keen on a challenge and would love my date to take me on. I think trust and honesty in a partner are special qualities.
New
 mansionfantasy
Chat
Like
About Me
I want to find my other half)) The name’s Kurt, I’m a well-mannered leader.
New
Kurt Vargas
Chat
Like
About Me
I’m an ambitious guy looking for my partner in crime. Ha-ha! Just joking 😂😂😂 I am a cool young guy who believes in miracles. I am seeking for MY girl!
New
Lesley Rockwell
Chat
Like
About Me
 My ideal date would be Paris. I’d like to meet a Frenchman and be wined and dined. My next partner needs to be well-built and tanned. I like a beard on a man too.
New
 wabbitsoor
Chat
Like
About Me
I’m Bernard, like the dog but with less slobber. Looking for a lady to go on longs with and share romantic, candlelit dinners.
New
stbernard
Chat
Like
About Me
I’m a dog-lover looking for someone with pets of their own for fun walks on the beach. I prefer a God-fearing lady of my age with or without kids, looking to start a new life, and have a new family. 
New
Tevin Spacey
Chat
Like
About Me
I’m sick of sharing the bed with only my dog. Does anybody want to come fill the space next to me? After a few dates, of course!
New
Nando1145
Chat
Like
About Me
I love animals, especially owls. Looking for a woman who’ll let me be the wind beneath their wings. I’m also a great chef ;)
New
Debonair1983
Chat
Like
About Me
Looking for a powerful woman who knows what she wants in life. A strong will and fiery personality are so attractive.
New
charlieloveschocolate
Chat
Like
About Me
After years of clubbing, I’m looking to settle down with a family-oriented lady, preferably older than me . I love kids, and would love to have some of my own soon.
New
Steven Turner
Chat
Like
About Me
I'm a lifestyle coach based in the city. I am looking for a lady to settle down with and start a family with, preferably one who likes city life.
New
Harold
Chat
Like
About Me
Into woodwork and kayaking. Would like to meet a girl with her own interests and a desire to discover new things together.
New
GordtheCarpenter
Chat
Like
About Me
Here to look for a mum to my two lovely daughters. If you can whip up their favorite milkshake in under a minute, you pass. Make it 3. :P
New
BeckMan
Chat
Like
About Me
Tell me what you're passionate about. I'm a recently single man ready for a new chapter. 51 years old and raising my teenage son on my own. Let's talk!
New
PapazelD
Chat
Like
About Me
If your ex-husband couldn't cook, don't worry - I can! Cooking is one of my many passions, & I'm looking for someone who loves to eat as much as I do. Tell me, what's your favorite dish?
New
 cook4u
Chat
Like
About Me
I'm Roberto, but you can call me Rob! I'm a playful, funny, and loving guy from Virginia. 43 years old. DM me if you're interested!
New
rob_m4ster
Chat
Like
About Me
Martin, 40, a single guy with 3 children. I like to watch football, visit the pub and see my kids! I would be happy to date local women both younger and older than me! Send a message!
New
MainManMartin199
Chat
Like
About Me
Need to find my gamer girl. I don't have any kids, but I do have a job, so no need to worry! I love Xbox, PS4, basically, anything I can play competitively. If you'd make a great partner, say hi!
New
 finalb0ss
Chat
Like
About Me
If you're a Ford type of gal, it's a no-go for me. Chevy ladies only! I own my own garage, have a decent-sized house, and am looking for a wife in my life.
New
 chevydude
Chat
Like
About Me
They say online is a great way to meet people, so here I am. I want a woman who has a good sense of humor, enjoys going for walks, and enjoys the little things in life.
New
 minifig
Chat
Like
About Me
A professional photographer with an undying interest in wildlife photography. Anytime I am alone, I cuddle my cats but I am looking for who could be my cuddler and share my interest. Let’s chat!
New
Kim Bartom
Chat
Like
About Me
I am an athletic enthusiast who spends at least two hours daily at the gym. I am ONLY interested in guys who share my interest, have a good body shape, and, of course, smells nice
New
William Milam
Chat
Like
About Me
Date me and you can get free haircuts. I love binging TV shows, anime, and cooking when I’m not working. 24, tall, sweet.
New
BarberD
Chat
Like
About Me
Footloose, fancy free, 25 and looking for love ❤️. If you want to have some fun then let's talk.
New
Jimbo95
Chat
Like
About Me
Congratulations you've just stumbled to my profile. This means you'll be a good taste gay man for me. Why don't you leave a message and let's engage in a quick chat...🤗
New
Don Cagan
Chat
Like
About Me
Italian food is great! I'm looking for a fellow foodie to travel with, check out new restaurants, and explore the world with. I'm not great at cooking though, so I'll leave that up to you!
New
 iheartpizza
Chat
Like
About Me
Gambling is fun! If you're willing to take a chance, bet on us! I'm 37, looking for love, and not afraid to take chances!
New
 dealcardz
Chat
Like
About Me
I feel like an amateur in all I do. So I need someone who I can relate to whenever I feel lonely. I'm gay and that's a fact I'm not ready to change. Please leave a message let's relate.
New
Daniel Dann
Chat
Like
About Me
I’m a single gay guy who hasn’t had a decent relationship for some time. I might be a little rough around the edges when it comes to flirting and smalltalk. But if you have patience, drop me a line.
New
Matthew Brady
Chat
Like
About Me
If you’re relatively new to Internet dating and feel you might be lacking in confidence where flirting is involved, I can assure you, you’ll quickly get used to it. We can exchange intimate messages.
New
Thomas Bird
Chat
Like
About Me
Have you ever been tempted to try bhangra? It’s a unique dance style, and you’ll find it an invigorating experience. What better way could there be for two gay guys to break the ice?
New
Sawyer Rojas
Chat
Like
About Me
Are you a fan of watersports? If you love nothing better than splashing around in the shallows, or if you’re more intrepid, kayaking expeditions, I’d love to hear from you. Let’s get aquatic together!
New
Chase Richard
Chat
Like
About Me
Colin E West. 23. I am trying online dating to find compatible bisexuals. I am a loyal, hardworking, loving person who puts his all into relationships. I hope to take things slow. 😋
New
BigColinE
Chat
Like
About Me
Hi, I'm Ryan and I want to enjoy some romance with an equal - if that's you, get in touch.
New
Ryry2020
Chat
Like
About Me
Hi Cuties, I’m Patrick Henry, 37, brother of six girls. I’m a soccer lover. If you don't find me reading in my leisure time, then I must be in the kitchen cooking for the family.
New
Patrick Henry
Chat
Like
About Me
There’s nothing quite like tickling the ivories. I’m not so keen on formal piano lessons, but I love tinkering on my own. There’s a spare seat for someone who would like to help me make sweet music.
New
Leo
Chat
Like
About Me
Over the lockdown period of 2020 I’ve really developed my interest in online quizzing. It would make my day to discover a male or female quizzer who could unite to form a highly competitive team.
New
Eli
Chat
Like
About Me
I’m here to find a potential soulmate who will bring me out of my loneliness because I’m socially awkward. I will describe myself as an introvert.
New
Quincy Jones
Chat
Like
About Me
 It’s fun to make new friends online and see how much chemistry we find. I promise I won’t bite unless you ask. Message me to see if we are a good fit in real life.
New
 Loverboy39
Chat
Like
About Me
 Skinny and grey. Don’t be scared about wanting other men. I am here to help you learn about homosexuality. If you want a kind man who will be patient with you in the bedroom, DM me.
New
 ebonyandivory10
Chat
Like
Love is Around the Corner! Join and Build a Happy Couple with Chicago Singles
Free registration
Mary williams
Mark woltz
If you’re looking for love in Chicago, sign up now.
Free registration
Kissing couple

The Most Reliable Modern Chicago Singles Dating Website

Chicago is mostly known for the chilly winters, the mouth-watering food, and teams like De Bulls and Sox. Singles within the metropolitan and surrounding areas between ages 30-50 are looking forward to meeting genuine and sincere partners. Visit our site and enjoy what the city offers for an ideal partner. Chicago is home to friendly people such that online dating is becoming exciting as time goes.

Our website enables you to interact with anyone online without breaking a sweat; meeting a perfect partner is now effortless. Our platform offers the best services that create bridges to finding a compatible partner. Whether you are new to online interactions or in search of a cool site offering chatting and real dating, then you have come to the right place. We provide unrivaled matchmaking features to all our users. We focus on facilitating easy meetups for all Chicago singles.

Be one of us by creating an account and registering for free!

Kissing couple Cupid banner

Create an Account to Start Flirting with Chicago Singles

A user's experience often depends on the services available and their activity level in any dating avenue. Our site has many active users—which gives you a higher chance of finding an ideal match. Regardless of where you live, finding a local match is easy because our site has a search option that narrows down your search to locals only. Join us by creating an account. Fill in all the required details and confirm your details via email to enjoy our features. Enjoy our premium package by upgrading your membership.

Chicago Dating: Flirt and Meet Gorgeous Locals

Interacting with local men and women is remarkably easy when you join us! No other site lets you enjoy unlimited flirting with local singles as we do. In any social platform, dating success is often determined by metrics such as how active you are and the services offered onsite. Once you upgrade your membership, we boost your chances of finding a potential match by allowing you to create and upload appealing profile videos. A profile video gives you an edge over other potential suitors by revealing more about you and providing an avenue for interactions. We also ensure that all our data is secured via an SSL connection - which protects your online information from hackers and manipulators. Moreover, we do not disclose your private information and protect you from being blackmailed or scammed by other users using fake profiles. Our interpersonal screening process ensures that only genuine and suitable partners are accepted. We have management strategies that ensure all our members are fully satisfied with our services by creating dating solutions that will pave the way to finding your special someone. We would love to hear your success stories after sampling our services.

Our website hosts dating services, including; meeting local men, speed dating, meeting mature singles, meeting local women, and chatroom dating. We strictly check your marital status, age, criminal record, and identity before approving your application. We also have a dedicated profile authentication team that ensures zero cases of misrepresentation of the applicants. We have professionally designed the website to protect and provide you the comfort you need because we want to create an environment that will enable you to find an eligible and compatible partner for a serious relationship. There are some benefits that only our users can enjoy. Most dating sites concentrate a lot on convenience but forget about compatibility. Our site creates connections that inspire closer relationships and emphasize convenience. We offer our members choices like; whether they prefer to browse profiles independently or explore our recommendations. They also decide if they want our experts to arrange one on one dates for them. We guarantee you professional matchmaking support that will lead you into a romantic relationship.

Sign up for free!
Join now
By clicking the submit button above you expressly consent to our Privacy policy including processing of personal data and use of profiling to find you matches and you agree to our Terms of use, and to receive newsletters, account updates, offers sent by Cupid