City Hookup Guide

Chicago Sex Guide: Bars, Clubs, Hotels, Restaurants

Getting laid with genuine girls in Chicago is much easier than you think! You don’t need to be an alpha male to get to chicks’ panties, just learn the rules and secret tips on how to get laid for real in your neighborhood. No matter where you’re from, whether you’re a Chicago resident or just a tourist, this Chicago sex guide is for you. Dive deep into the world of sex in this city and explore its naughtiest sides.

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The most effortless option for all lazy asses. You just turn on your laptop, browse the appropriate website, choose the most delicious pussy, and have a memorable one-night stand in Chicago. Usually people start with special hookup sites aiming to have orgasm with someone real. It means no one will fool around with you pretending innocent but horny and giving you fucking nothing at the end. Every gal on such a platform wants you to rape her pussy lips.

Looking for sex in Chicago this way you may end up in a stranger’s bed in an hour after entering the website. It’s because they usually offer easy and effective search tools aimed to help you in finding only the most fitting birds. Filter them all depending on your sexual preferences and get zero disappointment when you ask for anal. If a girl is up for that, she always points this out in her bio. Sometimes famous webcam models or porn stars register on hookup sites as well, so you might become the luckiest guy on Earth after having sex with such a lassie for free.

The juiciest sex cam models from Chicago

Aaliyah Love
Aaliyah Love
Aaliyah Love
Followers: 5k
Morgan Lee
Morgan Lee
Morgan Lee
Followers: 7k
Lana Rhoades
Lana Rhoades
Lana Rhoades
Followers: 9k
Emilly Starr
Emilly Starr
Emilly Starr
Followers: 12k
  • Aaliyah Love. Truly a webcam veteran like she says herself. She started showing off her kitty on cam at the age of 18 and then became a well-known porn actress. She’s a petite blonde and an image of all guys’ teen fantasies. Google her and you’ll know why!
  • Morgan Lee. This hottie has the face of a Korean girl and an ass of an American slut. Isn’t this the mix every jerker dreams about? She’s already a popular porn actress but isn’t ashamed to finger herself on cam to let all the hungry dudes admire her and wank.
  • Lana Rhoades. Looking at this cute face, you would never guess what dirty things she can perform on cam and in bed! Fucking her pussy and asshole with huge dildo, sucking it and pretending it’s a real penis, squirting like a wild cat — she definitely knows how to tease hungry wankers.

I want to meet girls in Chicago: What’s on offer?

Dude, to understand what kind of chicks might be waiting to swallow your cock. Just have a look at Cindy Crawford! How would you love such a Chicago hookup? She’s one of the brightest representatives of locals and calls the city her home. She reflects a classy attitude to everything and full freedom in mind. Do you already imagine what borders such a chick might establish in bed? Right, none! And almost every skirt in the city is just like that!

Despite the age, every pussy wants her juices to flow. Young virgin students, hungry divorcees, experienced milfs — choose what makes your shlong the hardest, as Chicago has a lot to offer.

The best offline places to have sex in Chicago

Where to get laid in Chicago? Possibilities are really boundless in the 3rd biggest city of the US! Bars, clubs, restaurants, parks, gyms, exhibitions, you name it. Lots of singles spend wild nights in Chicago regularly and you can be one of them with the list of best places to go for a pussy hunt. Write it down!



Nothing is easier than to buy some skirt a beer or sweet cocktail and fuck her in the toilet an hour after. But how many times have you really succeeded in it? I guess you wouldn’t be reading this if many. You just choose the wrong places! These are the best hookup bars in Chicago where chances to bang one of the sexy visitors are high. Either because of a bar’s atmosphere or just a kind of people hanging out there — both works on you.

  • Sportsman's Club(948 N Western Ave). Classy atmosphere, low lights, craft beer, wine and tasty cocktails will blow your mind! What else is needed to catch some yummy ass?
  • The Green Mill(4802 N Broadway). Drink, talk, listen to jazz. A place with history and sexy visitors. Perfect destination for you, agree?
  • The Violet Hour(1520 N Damen Ave). Stylish cocktail bar with ability to take drinks to go with you. Choose chic, order her some Whiskey Sour, take a few more for takeaway and go find some hotel!
  • Cove Lounge(1750 E 55th St). Feel yourself part of the Al Capone gang in this wooden interior. Girls love bad boys, remember?
  • The Ladies’ Room(2957 W Diversey Ave #2957). Its audience comes from the name itself! Lots of horny ladies that enjoy drinking cocktails and having fun are on the hunt right there.


To pick up a doll in the nightclub is a classic. The atmosphere of excitement, loud music, rivers of cocktails with vodka. All smart guys go to the hottest nightclubs in Chicago when they’re up to some fuck. Just dance and don’t be shy to rub your little pecker gently on cutie’s ass. If you don’t get a slap in the face after this — she’ll spread legs for you tonight. These are the best spots to look for erotic adventure:

  • Berlin (954 W Belmont Ave).
  • Danny's (1951 W Dickens Ave).
  • PRYSM Nightclub (1543 N Kingsbury St).
  • Underground (56 W Illinois St).
  • Debonair Social Club (575 N Milwaukee Ave).
  • Spybar (646 N Franklin St).
  • Stereo Nightclub (5616 W Diversey Ave).
  • TAO Chicago (632 N Dearborn St).
  • Transit (1431 W Lake St).
  • Late Bar (3534 W Belmont Ave).


Not the most obvious spot for sex dating in Chicago, but sometimes chicks really come to restaurants not only to dine. Observe their behavior, how they dress, and what they order. If she’s single at the table, wears heels and a mini-skirt, and sips wine — grab her without any hesitation. Start with a small talk and then make a hint that you would be happy to continue the dialogue in her bedroom. If she doesn’t refuse right away but still pretends to be modest, keep trying and end up sucking her clit at the end of the day. These are the best Chicago restaurants to hook up:

  • Virtue Restaurant (1462 E 53rd St).
  • Lula Cafe (2537 N Kedzie Blvd).
  • Tzuco (720 N State St).
  • Daisies (2523 N Milwaukee Ave).
  • Boka (1729 N Halsted St).
  • Osteria Langhe (2824 W Armitage Ave).
  • Demera (4801 N Broadway).
  • Elske (1350 W Randolph St).
  • Marie's Pizza & Liquors (4129 W Lawrence Ave).
  • Smyth (177 N Ada St #101).

Where to stay for Chicago hookups?

Provided you’re a sex tourist and looking for a good spot to sleep at while your pleasure chase I have it all covered for you. The quality of services offered in these hotels depends only on the sickness of your wallet. Consider these sex hotels in Chicago not only as beds to sleep on but also as places for your fucking session with local birds.

  • Home2 Suites by Hilton Chicago River North (110 W Huron St): around $115 per night.
  • Sofitel Chicago Magnificent Mile (20 E Chestnut St): about $130 per night.
  • Homewood Suites by Hilton Chicago Downtown South Loop (59 E 11th St, Chicago): around $93 per night.
  • Millennium Knickerbocker Chicago (163 E Walton Pl): about $80/night.
  • Embassy Suites by Hilton Chicago Downtown Magnificent Mile (511 N Columbus Dr): around $148 per night.
  • La Quinta Inn & Suites by Wyndham Chicago Downtown (1 S Franklin St): from $80 per night.
  • Hotel Essex Chicago (800 S Michigan Ave): around $100 per night.
  • Hyatt Regency Chicago (151 E Wacker Dr): around $182 per night.
  • LondonHouse Chicago, Curio Collection by Hilton (85 E Wacker Dr): about $129 per night.
  • Best Western Grant Park Hotel (1100 S Michigan Ave): around $60 per night.

Sex clubs to try in Chicago

Those who don’t like to beat around the bush and are determined to feel the taste of local pleasure will enjoy numerous sex clubs. From first sight this city is famous for parks, breweries, and high-class restaurants. But only a few knows how much sex is appreciated there. Residents organize numerous parties and gatherings where everyone just has sex and enjoys it in all forms. Let’s see what’s on offer.

Killing Kittens

These are upscale sex parties where women always come first. It’s actually a motto of this company, and they do their work proudly and openly. The approach is modern and obviously a big team is working on this brand. Do you imagine how many dolls visit such events if they’re promised to be the center of attention? Right, dummy! That’s your chance! While partying with these guys sex isn’t obligatory but everyone fucks there without any borders. Only one drawback — parties are only for Killing Kittens members and men can only be invited by members. So contact them to become such a VIP.

The Lux Social Club

Here you have a chance to feel rich like a shit. All parties are held in the big mansion with different play areas, hot tube, pool, and private spaces. The audience is usually mature, so everyone knows what it’s all about. Everyone is allowed in this community for a little fee. If you aren’t ready to bang they’ll welcome you with relaxing games and won’t force you. But who the hell are you trying to fool? Of course, you’ll fuck there! Don’t forget to dress well as no hoodies and jeans are allowed.

Sins Center

Sex parties that are held every weekend! So you shouldn’t worry about missing any fun in case you have only a day or two for sexual exploration of the city. The location is secret and you’ll know it when contacting them. Gatherings are usually served with drinks and some food, so you’ll have a chance to eat a bit before your wild sex drive in a private room. All genders are allowed, so take care of your asshole.

How and where to find a Chicago MILF for a memorable hookup?

No surprise, a horny hookuper like you will desire to explore not only local young birds but MILFs nearby as well. And in such a big city as Chicago, you get lots of options on where to find them.

Chicago Milfs

Top spots to meet mature ladies in Chicago

These are the places where you'll most likely come across single (and not so single) MILFs in Chicago:

  • Art galleries. Wanna have fun with a mature and intelligent lady? This is where you have to go! Some say that sex with smart women is even better, and they're up for more experiments. So pay a visit to museums such as Gallery 400, Smart Museum of Art, and Museum of Contemporary Photography. The chances you meet a bird out of your league here are high, so fucking her will be even more pleasurable.
  • Yoga classes. Sexy Chicago women try hard to stay fit, no matter the age. Moreover, they care about their mind no less they do about the body. So try yoga studios if you're looking for local MILFs in your area: Yoga Now, Yoga Loft Chicago, Essence Of Life, 105F Chicago's Original Hot Yoga.
  • Supermarkets. What does a woman in her 40s do every day? Grocery shopping, dummy! She most likely has either kids or pets to feed, so finding local MILFs in supermarkets is an excellent idea. Some spots to check: Mariano's, Whole Foods Market, and Jewel-Osco.
  • SPA centers. While you puzzle over where to get real MILFs near me, wise guys already hang out at SPAs to hook up with sexy mature locals. Yes, buddy, heading to SPA you have all the chances to meet a cougar, as women in their age know about the importance of pampering themselves and have money for that. Recommended spots are: Luxe Spa Boutique, Allyu Spa, and Urban Oasis.

Tips on successful hookups with Chicago MILFs

Going to the places where MILFs usually hang out isn't enough to bang them. These chicks require a particular approach. And this is what I mean:

  • Be confident. Mature dolls won't ever waste their time on a man with low self-esteem. They've seen many guys like that and desire someone who knows what he wants.
  • Engage her in a casual talk. I hope you don't hope to start a conversation asking whether she's up for some fuck, right? MILFs in Chicago get wet because of deep and smart chats. Amaze her with your knowledge first and then, eventually, state your intentions.
  • Give compliments. Sexy Chicago women miss nice words from men of their age. Those jerks often take them for granted, and that's what MILFs are trying to escape with younger dudes like you.
  • Don't hide your age. The fact that you're younger is actually what turns her on! So why to pretend then, huh?

3 main tips for a memorable Chicago hookups

Chicago sex scene: Why chances to have sex there are high?

Getting laid in Chicago is much easier than it might seem from the first sight. Not only big companies like Boeing and Northern Trust it’s famous for. In the daytime, big bosses make money. At night, they have fun and fuck. Don’t you desire to be one of them?

Everyone has a casual sex in Chicago just because its population is about 3 million people. Even the biggest loser puts his horny pecker in a warm juicy hole from time to time there, so such a sex-machine as you are will definitely find a place for some dirty play. And knowing that Al Capone was conquering local hotties decades ago you can’t help but get inspired to find some qualitative sex in Chicago. Thousands of people choose this city as a final destination to settle down because of its numerous parks and promising career prospects. What the hell, they also choose it because of breweries!

Do you know Chicago is number 1 US city in the list of the Most Craft Breweries? Do I really need to explain what it means? Use your brain, jerker! Lots of sexy birds taste local beer every night and after a glass or two are ready to continue the party somewhere else. Isn’t this the easiest way to sneak under a girl's dress?

By the way, many famous people come from Chicago. And I’m sure they all had wonderful sex experience in this city. Barack Obama was also living there for a long period of his life. Are you really so naive to believe he was doing only his political career there? If you’re lucky enough maybe one day you’ll fuck a local hoe that had sex with president years ago! Jesus, that sounds pretty exciting even to me.

But the most outstanding person who definitely knew where to find sex in Chicago was Hugh Hefner. That horny dick was a professional in searching the tastiest bunnies with delicious curves. Damn, he had that sex intuition! No surprise the original Playboy Mansion was in Chicago! In 2018 it was sold for more than $2 Million. Isn’t this the best proof this city knows something about pleasure and cherishes it? You may continue Hef’s career or simply enjoy local biddies now and then.

Book a plane!

Chicago is a city that has a lot to offer by means of sex and pleasure. Local chicks aren’t ashamed to live their life to the fullest and try as many cocks as they can. You’ll be surprised with the number of sex club functioning there and that’s the best proof of how open-minded residents are. Isn’t this exactly what your poor prick was looking for? The word “taboo” doesn’t exist when you’re in Chicago. What happens in Chicago, stays there. Get on the plane!

Secret tip from a local Chicago hookuper

No one will tell you better about the sex scene in Chicago than a local sex dater. But not only the best places to get laid matter when you’re a tourist. There are some districts you better avoid if you don’t want to have trouble. I’d recommend you not to look for sex in West Garfield Park, North Lawndale, Englewood, Riverdale, Chatham, Austin. But you’ll definitely hang out safely in the Loop, Gold Coast, Lincoln Park, West Loop, Streeterville, Wicker Park. Just stay close to the city center, dude, and your dick will be secured.

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