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Casual Encounters

9 Best Places to Find Chicago Casual Encounters

Dating sites seem to be a waste of time for most people if they want actual Chicago casual encounters. Luckily, there are great alternatives for people who want to have a taste of the Chicago dating scene.

Porn Inquirer is your only source in helping you with your next casual encounter. That’s why we created a list of the 9 best places to find singles for finding hookups. Just know that you can also check out these 3 sites if you want better chances to meet a guy or a woman for fun.

IconSiteScoreTry it out
Top Pick
Adult Friend Finder

Adult Friend Finder

  • Most Recognized
  • Largest community
  • Very Discreet
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Ashley Madison

Ashley Madison

  • Discreet Affairs
  • Lots of Milfs and Cougars
  • Easy to Use
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Also Great


  • Members are DTF
  • Anonymous Chats
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Top Spots in Chicago for Casual Encounters

a woman from chicago using her phone while inside a nice bar

Since Chicago is hailed as the best city for dating, it comes as no surprise that there are many cool spots you can visit for casual hookups, no matter where in the city you would be. Just browse our list below and see if something gets you interested.

Tao Chicago

Tao Chicago is probably one of the hottest places to boost your “night” life and have fun in the city. Apart from its stellar service, it’s where cool kids come to drink and party. We’re sure you’ll find hot men and women ready to hook it up in no time.

Who knows? You might see that “local celebrity” you’ve been gushing about from the OnlyFans Discord.

Kinston Mines

Founded in 1968, the place is the oldest blues bar in Chicago and the rest of Illinois. It has won several awards and has become the venue of cool blue acts of great renown. We put this in our music category, if you want to meet a guy or a girl who’s into music but also someone you’d like to fuck.

Prysm Nightclub

Prysm delivers state-of-the-art live entertainment with world-class DJs, 3 full bars, 2 levels of space, VIP suites, and 4 restrooms (probably for making out and having fun?). It can host up to 850 people. Think about it, 850 potential singles in one room. No need to browse profiles on the Monkey App when you’re in here for sure.

MASQ Chicago

MASQ is a bar like no other. You can dance the night away and meet eligible men and women (regardless if they’re straight, gay, or transgender). If it’s a party life you’re after, this place is it. We’re sure that after a few drinks and a friendly chat, you’ll find yourself going elsewhere with a man or a woman of your choice.

Stereo Chicago

One of the best places in Chicago that you shouldn’t miss for your life is this bar. Stereo hosts some of the hottest parties with various themes every night. It’s age strict, of course, only accepting everyone who’s 21 and above. Get face-to-face with a hot single in every corner today here. Forget Dirty Roulette because this site is certified fun!


If you want something more relaxed, perhaps this place is where you’d meet the fine men and women of Illinois. Just make sure to bring enough money because of the handcrafted cocktails you’ll be ordering.


Want something fun and different? HIGHLINE offers classic arcade games on top of delicious bar food and drinks. It’s no wonder why singles are flocking here during after-hours. Perhaps you’ll even find hot women to spice up your evening to send some dirty Snapchat messages with you.

The Underground

Want to get your blood pumping? The Underground might be a good match for you. The heart-pumping music, the live crowd, and the fun dance floor, hey, that could be a sign that you should be here.

Debonair Social Club

It doesn’t matter which types of men or women you meet, you’re sure to have fun in this swanky club!

Do Casual Encounters in Chicago Lead to Casual Sex?

Yes! Finding the ideal guy or woman for dating and hooking up with here in Chicago is easy. But if you ask us, the apps we featured earlier would do you just good, not to mention these 3 apps below.

IconSiteScoreTry it out
Top Alternative
Well Hello

Well Hello

  • Easy to Use
  • Members Ranging All Ages
  • Free Membership
Try for Free
Sometimes Good


  • Ladies Message First
  • Beautiful Platform
  • Many Guys
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Typically Reliable


  • Widely Known
  • Over Saturated
  • Lots of Male Members
Try for Free

Guide to Chicago Casual Encounters

chicago couples dating on a fancy restaurant

If you’re curious about how people hook up in Chicago, we’ve prepared a quick and easy guide for you to follow. These simple tips can help you with your sexy encounters no matter what.

Be proactive

Any man or woman wants their partner to be present. That means they must be engaged in the conversation and not just deliver lip service without actually delivering on what they say.

Practice consent

Before you go down on someone for some quality sexy time, make sure that you’re both on the same page with what you want to do in bed.

Be present

Do you know what a woman wants in their dream guy? It’s being present with them. That simply means apart from creating spice in the bedroom, they should always be attentive and listen to their needs and what they want.

Proven Way to Find Casual Encounters in Chicago, Illinois

If you’re single and ready to mingle, there are hundreds of ways to find casual dating and hooking-up opportunities in Chicago, Illinois. But as we’d say, the top 3 sites mentioned here are your best bet if you want it fast. Just create an account, find some matches with the singles’ profiles who live in your area, and you’re about to meet cool men and women for hot fun in no time.

James Bander

My name is James and I've been in the adult and porn industry for 15 years. I've been a writer in the space for 5 years covering all aspects of the industry including sex cams, porn tubes, adult dating, chat sites and sex toys. My writing has taken me to many adult conferences such as AVN and inside many companies. I love the industry and can't wait for readers to consume my honest and deeply research articles.

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