Chicago is perfect when it comes to finding an unforgettable hookup. The city is full of Midwestern vibes, and there’s no shortage of festivals, parties, and events. It takes skill and confidence to find a casual hookup Chicago — if you know the hottest places in Chicago, you will not have issues looking for friends with benefits.
In this post, we’ll discuss where to find the creme-de-la-creme of the 2-million city. You’ll take a short tour of the hottest bars, night and strip clubs and will find out how to act and what to say to be likable in Chicago.
How to pick up hot Chicago girls
Just as the city itself, Chicago girls come with class and flair. They are ambitious, outspoken and confident. Girls in the city work hard to stay in shape — though most are not too slim, they look fit and good-looking.
People in Chicago are funny and open-minded — be sure to answer questions with confidence and an occasional joke. You can find a good girl everywhere in the city — yet, in my experience, River North gathers the largest and most attractive crowds. As a rule of thumb, the city goes to bed early — you are likely to find evening Chicago streets empty.
Hookup tips in Chicago
Although the best places to look for girls heavily depend on what type of day you’re spending to look for a hookup, there are a few general rules to know regardless of your favorite time and place to find friends with benefits.
To start with, be the one to approach a girl. Chicago women will not be freaked out by an assertive, outspoken guy who makes the first step and asks a girl out. Avoid small talk — instead, consider cutting straight to the bone. You need to be able to look the girl in the eye, and not just send pictures in the messages of adult sexting sites.
Tips for daytime
Chicago is the hot spot for gaming and shopping — that’s why most single girls are scattered around Michigan Avenue. If you’re looking for ambitious women who know how to secure the bag, take a stroll around the Loop business district. If you’re looking for hookups during lunchtime, look for partners in cafes and bars.
Although most busy women look for hookups online, don’t be afraid to approach a beautiful girl personally — people in Chicago still dig the old-fashioned bar hookup.
Tips for nighttime
Although there aren’t as many party girls in Chicago as there are in NYC or LA, there are many hookup-friendly places. Generally, the night club crowds are not as uptight and are super approachable.
To kick it off with a Chicago girl at night, get them drinks, complement their look, and you’re hookup-ready. As for the best party places to have hookups in Chicago, check Magnificent Mile — the Michigan-Avenue-based venue out.
Chicago is a pretty great place for a Chicago hook up or getting laid in general. The girls are welcoming and friendly. All you need to do is to be polite, dress well and charm them by buying them a few drinks, complimenting them and you will be good to go.
Chicago has a couple of bar districts — Wrigleyville is, undoubtedly, the livest one. Wicker Park and Lincoln Park are other bar-friendly areas you can check out.
Chicago is more of a hookup-app than a bar city. Having said that, there’s no harm in trying your luck at a bar — there are a handful of atmospheric places downtown. I’d start a party errand by visiting Arbella. The place showcases Chicago’s cocktail scene to the fullest. A selection of classy drinks and meals attracts plenty of 25-30-year-old woman to the place.
If you want to drink till four, consider visiting The Owl — one of the best hookups bars Chicago that doesn’t go to bed early. The venue in Logan Square is the last stop for most parties — that’s why most people look for someone to go home with exactly here.
The Owl works with DJs who create custom mixtapes every night. The beats here will never get stale, and there are usually many people around who’re up for dancing.
Chicago night club scene is truly one of a kind — there are many places with cheap entrance fees, quality drinks, and solid music. When I visited Chicago, SteppenWolf Theater was the first place I went to — it’s a mix of a nightclub and a theater. There are spacey seatings, a wide selection of drinks, and I haven’t seen their plays at any other theater. Basically, visiting StepperWolfTheater would feel like half a chill-out and half a date.
Chicago has many nightclub gems I’d suggest checking The Outtaspace out. There are dim lights, live music, and a cozy atmosphere — what else would you want? The crowds could be larger — the good news is, everyone at The Outtaspace is friendly and open-minded.
Chicago scores high on my adult-entertainment list. There are many strip and hookup clubs around town — I had a hard time narrowing the circle of favorites down. To start with, I loved “Ricks Cabaret Chicago.” The place has comfy leather seats, well-trained and good-looking girls, and friendly staff. I love the look of it — the brick walls and the dim lights.
Next up on my go-to list of Chicago strip clubs — Bare-Assets. The place runs a killer adult arcade game, there are TVs with quality porn all around in case you feel like relaxing after a workday. The place is welcoming to people of both sexual orientations.
You can include Chicago Cuddles or Admiral Theater to your list of must-visit places for an unforgettable night.
Editor's pick for May, 2020
Best places to meet girls
If you want to visit nightclubs and hookup venues that welcome the largest crowds of single girls, here are the places a male hookup-seeker should definitely check out:
- Buddy Guy’s Legends;
- House of Blues;
- Nacional 27;
- Kingston Mines;
- Debonair Social Club.
Best places to meet men
Now that I covered the most lucrative places to find a single lady for a Chicago hookup, let’s talk about meeting guys in town. There are many places to explore for getting laid — here are the ones that kept me entertained during my numerous visits to Chicago.
I had a fair share of prospective hookups come at me at Slippery Slope. The place is so chill and free, with a dancing area and an intimate zone upstairs. Here, I could chat with guys to see if I liked them enough to spend the rest of the night together.
Bub City is another place that, in my opinion, every Chicago hookup enthusiasts should visit. Although it is just a BBQ spot, I’ve seen and met many singles there — had a few drunk makeouts as well.
Finally, the Berkshire Room is another worthwhile place in Chicago. It’s a classy singles bar that is not as expensive as it may seem, judging by the interior. The crowds here are huge and sophisticated — the guys you pick up here will not be dull as a table lamp.
The best chance of hooking up and getting one night stand
The hookup scene in Chicago is wild. You stand a chance of leaving with a hot partner regardless of where you go — to a coffee shop, a nightclub, or a karaoke bar — on that note, Sakura Karaoke is one of my favorite places that oozes the Midwestern chill-out vibe.
210 Live is another impressive venue — other than a large crowd of mainly single visitors, there are live music and engaging performances five days a week.
A bit of generic advice before you start looking for hookups — keep an open mind as you’re visiting venues. Some of my better hookups were not with conventionally attractive people — anyone might surprise you. Don’t be afraid to loosen up and get out of the box. And guys who like older women should remember: in Chicago, you do not always have to get paid to date with cougars.
Online dating: best hookup sites
Chicago has over 3 million singles — every third city resident has a dating app account. The Tinder/OkCupid/you-name-it obsession has taken all over the city — right now, your chances to find a hookup via an app are higher than by doing it any other way.
Although it should go without saying, it’s not enough to just create a dating profile. Before trying your luck on the online dating scene, make sure you know which platforms are popular in Chicago right now. Spoiler alert: these ones. As well as some of the real hook up sites that are popular throughout the United States.
Pure is a short-and-sweet hookup app that helps you find a hookup in an hour. All profiles are self-destructive — there will be no witnesses to your romantic adventure, along with the risk of data leaks.
Mingle2 has yet to prove its worth, although it has been taking Chicago by a storm lately. It’s an easy-to-use, swipe-based tool for online dating and hookups that helps find hot Chicago girls in the area.
Despite the mixed reviews the platform has been receiving lately, Tinder is still an evergreen dating website with the largest hookup selection. Here, you can find people of all genders, ages, sexual orientations, body types, and ethnicities to spend a night with.
If you’re still unsure of what to do or where to go for getting laid in Chicago, I decided to answer a few common questions about the city’s hookup scene to help newcomer hookup enthusiasts out.
Where to get laid tonight in Chicago?
I wrote about some of my favorite hookup venues above — however, if you’re in for a definite list of my Chicago sex scene favorites, here are the places I am itching to come back to someday:
- The Hangge-Uppe;
- El Hefe;
- Slippery Slope;
- Bunny Slope;
- East Room;
Where to hook up in Chicago?
If you want to get a fire-sure hookup in Chicago, I would check coffess shops, night clubs, and strip venues out. Also, don’t forget to create a dating app profile when looking for one-night-stands in town — hookup platforms like Pure are super hyped about here.
Here are my favorite Chicago hookup venues:
- Kingston Mines;
- Buddy Guy’s Legends;
- House of Blues;
- Stereo Nightclub;
- Nacional 27;
People from Chicago you see on Pure are online right now
Our users are making it clear: they want to hookup within one hour.
Unlike most sex websites, we do not have awkward questionnaires. The service works as a local sex app based on your location: the first thing you need to get a match is your registration.
After your sign-up, you will see lots of people in your district with the distance between you shown. To try your fate, you can like, dislike or super like other members to come together.
The last step is a flirty conversation, which starts if your chemistry is mutual.