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The Expert’s Guide to Meeting Cougars in Chicago in 2023 - Where To Go And How To Date Them

Chicago cougar sipping wine by a window

Wherever you go, you’ll see cougars in Chicago, so you know it’s a great place to find some older women to date. Spend a day out and about in the city, and you’ll notice plenty of gorgeous older women. They might be emerging from their yoga class at Yoga for All Beings or looking for organic produce at Morse Fresh Markets. In any case, if you’d love to date a cougar, our city gives you plenty of options.

Getting beyond the first conversation to an actual date isn’t effortless, though. It can even be intimidating unless you know where to look. To help you out, we’ve put together a list of our favorite cougar bars and hangouts. These are the places where we’ve had the best success meeting single cougars (not just the Viagra Triangle).

The city is full of energy and bursting with mature women eager for younger men. Head over to these spots and share your experience in the comments section!

The Best Places to Find Cougars in Chicago

It takes some practice to get better with cougars, and you don't waste your precious hooking up in some random bar/club only to find it's loaded with uni students and young singles.

They're fine, but you came for cougars, didn't you?

We packed this guide with a ton of cougar-friendly venues to suit all tastes of all men, and to kick it off, here's a shortlist of our absolute favorite places/apps to meet hot cougars in Chicago. We made it specifically for guys who're only in Chicago for a couple of days and want to have some fast fun.

Chicago single women sitting near the gold-tiled wall at Stereo Nightclub


Single cougars in Chicago love to go out dancing at Stereo Nightclub

Stereo Nightclub is the perfect nightclub if you’re looking for great music and an overall warm atmosphere. This is the one nightclub in our city that is both friendly and filled with Chicago hotties. You won’t run into the typical snotty clubgoers while partying here. In fact, we’ve come across some pretty hot older women while grabbing drinks here.

The club is always entertaining and the DJ acts are pretty remarkable. Along with the great music acts, you can always count on reliable service here. You won’t be stuck waiting at the bar for over 20 minutes trying to place a drink order. Overall, this is a fantastic spot if you’re willing to step out of your comfort zone and dance with gorgeous women in order to have a good time.

Homepage of AFF

No doubt our favorite Chicago cougar dating app is AFF when we just want something casual or physical

Our big, bustling city may be full of people. But it’s hard to find someone who wants the same thing you do. Admittedly, a lot of cougars want to get laid, but there are some who prefer to be wined and dined. If you want the former, then AFF (with their great free trial) is a great place to find them.

AFF users are interested in one thing and one thing only: sex. Here you’ll meet singles who just want a quick fling, a friend with benefits or a one-night-stand. Lucky for you, a huge percentage of AFF users are in their 30s and 40s, so you’ll meet plenty of Chicago cougars there.

This is our favorite option to meet cougars to take home around the city with ease!

What we love about AFFr the most is how easy it is to search for people you’ll click with. You can search by location, kink or even cup size, so you’re bound to find the right cougar for you. None of these women want to be your girlfriend. But if you get along well enough, a relationship is just a bonus.

Meet dozens of cougars in Chicago who all want to get steamy with you on AFF!

Try AFF For Free!
If you actually want to meet single cougars who are more interested in fun in the bedroom than a long-term relationship you need to check out AFF's free trial with this link. We've spent many months testing out 100+ different sites and apps to meet cougars and AFF has consistently been the easiest way for most men.

Home page of eHarmony

eHarmony is the top way to meet cougars if you want a relationship (try it free)

When it comes to meeting a lot of cougars quickly, especially those interested in dating younger guys, there isn't a better option than eHarmony (which just so happens to have a great trial) if you want a real relationship. Older women are often just too busy to spend a lot of time in bars and clubs so many of them have been looking online to meet guys. In fact, a lot of them are ONLY looking online these days.

If you're not spending at least a little time on eHarmony you're going to miss out on a lot of opportunities!

There are a lot of dating sites and apps out there (and we've tried just about all of them in our cougar dating site review) but none of them really deliver as well as eHarmony does. There are a few reasons this Chicago cougar dating site works so well:

There are a lot of cougars in Chicago using it

There are more popular apps and sites out there but they just don't have the cougars. eHarmony has over 33 million active members and many women on this site are cougars. There is no reason for a non-cougar to even consider signing up!

Instead of scrolling through hundreds of profiles hoping to find an attractive single cougar, especially one interested in dating both younger and older guys, they are all right here. It saves so much time and frustration!

These cougars actually want to meet up

If you've spent any time on other apps you know that a lot of the women that use them are really just looking for attention. They don't want to really meet a guy in person but they're happy to collect compliments and stroke their ego.

When you use a more specific option like eHarmony you avoid a LOT of those time-wasting women. You only use a site like this if you're serious about meeting guys and not just leading people one.

It makes a huge difference in the response rate from your messages and the number of dates you can actually setup.

A really good mix of Chicago cougars who want short and long-term

eHarmony does a great job of attracting women interested in both short-term fun and a real relationship. The other top sites out there can be great but tend to attract a very specific type of woman.

eHarmony trial

If you haven't tried it out yet give eHarmony's trial a shot. You have nothing to lose and you can't expect to get new results without changing up your approach. Guys who really want to find a cougar aren't going to be able to do better elsewhere (in our experience).

Classy cougars in Chicago get drinks at LUXBAR


If you're looking for hot Chicago cougars, they're at LUXBAR

Looking to meet a cougar somewhere more subdued and elegant? LUXBAR will provide an easy solution for guys trying to figure out how to find local cougars on the prowl for young men (more details here).

This bar and restaurant excels at food and has a great track record of bringing cougars in most nights of the week.

You can sit outdoors or inside. The outdoor seats are much more scenic because of the beautiful landscaping. But you have a better chance at meeting a cougar at the bar inside. They also have both classic and seasonal cocktails, along with diverse wine and beer options.

Even during mid-week, many cougars go here after work. Once you hit it off with an older lady, you can make a thoughtful gesture by sharing dessert with her. If she has a sweet tooth, she’ll adore the famous Snickers Pie.

Women at enjoying an evening at Richard's Bar


The Apps Dating Coaches Recommend Most To Meet Cougars

More and more older women are only using apps and sites to meet guys, especially younger guys. You need to be on at least one or two apps now if you want to get the best results you can. These are the apps that give normal guys the best success meeting cougars:

SiteOur ExperienceOur RatingFree Trial Link
Best Hookup Site Cougars
Experience Highlights
Experience Highlights
  • The best way to meet cougars for hookups by far
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
Try AFF For Free
Best For Relationships
Experience Highlights
Experience Highlights
  • Easily the best option for long-term relationships
  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
Try eHarmony
2nd Best For Hookups
Experience Highlights
Experience Highlights
  • 2nd best option to find hookups
  • Attracts an older crowd than most hookup apps
  • Pretty popular
  • Great free trial
Try Passion

Top Chicago Cougar Bars and Cougar Clubs

With almost three million people living in Chicago, it's fair to say that there's always something for every taste. There's a lot of cougar bars in Chicago, and even the villages around it. All of them are different in both style and the experience they provide. This is why we recommend that you hop between bars till you find the one that suits you.

We also recommend that when you find a neighborhood with lots of hot cougars then you should stick to the bars of that area because most cougars prefer to party close to where they live for age and time restrictions.

These are the best cougar clubs and bars in Chicago right now:

Like I said earlier, Chicago is loaded with cool pubs, lounges, and clubs in every major street.

We tried to mix things up to suits your taste, and budget. We also made sure that all the mentioned venues are still open, especially after Covid.

So many venues either relocated to reduce expenses or completely shut down "forever" because they can no longer afford to close for more than one year without work.

2 hot Chicago cougars during the day at LuxBar


Meet Cougars in Chicago during the day

Talking to strange women can be a huge discomfort to most men, especially when she's smokin' hot and everybody's watching. Surprisingly, however, this is the best time, and place, to meet hot women.


Their guard is down and the competition is low..

She doesn't expect many guys to hit on her because it's not something most men can do either out of bravery or lack of skill. Also, and unlike in bars and clubs, you won't find ten men competing for her attention. So it's just you, and your social skills.

It's easy, you just need to practice consistently.


In any of these Chicago spots:

So what to do exactly when you see a cougar you like walking on the streets of Chicago?

Make eye contact, walk towards her and say hi.

If this is something you don't usually do, then stick to a compliment...something like, "I like your style or you look like a cute ninja (if she's in all black + a black face mask).

It doesn't matter what to say...It's how you say it that matters,

Again: It's how you say it

Women are the masters of social cues. They smell social anxiety from miles away. So try your best not to come from a frame of mind like: "OMG, she's so beautiful, I hope she likes me."

Instead, think of it as:

"It's a free world and I'm allowed to stop a stranger on the street and give her a compliment. Nobody does that, so I'm brave. And I'm making her feel better so I'm doing her a favor....,

If she rejects me, it's still cool. At least I didn't cave"

Your mind probably won't believe you at first, but the more you push with this frame, the more believable it will be...and you will look super confident to her.

A hot Chicago cougar with a cute hat at LUXBAR


The Guide to Cougar Dating in Chicago 

We showed you where to meet them, now we show you where to take them hot Chicago cougars.

And if you think all cougars want the same thing then you're probably mistaken. Unlike younger girls, who mostly hook up for fun, cougars know what they're signing up for where before they meet you.

And where/how to date them will depend on that goal.

For instance, you can't take a cougar to dinner or a comedy club on the first date when all you both want to do is play hide the zucchini at your place.

You do dinner/comedy clubs when you wanna build some connection, either after you've slept together and want to take it seriously, or early on when she still hasn't decided what to do with you.

So, we divided the venues into three categories depending on your goals (and hers)

If you just want to keep it casual take her to a lounge

If all you two want is a hookup, then a romantic bar or rooftop will do the job. You want a place that is romantic enough she doesn't get bored, but still not noisy so you can hear each other.

Also, don't pick a venue too far from your place - or get a car. It will be hard to take her home when it's 11:30 pm and you're 45 minutes away from your place.

A few of our favorite Chicago lounges right now that fit this description are:

If you're taking it slow, then a fun activity will do the job

Some cougars just don't wanna waste time on the wrong man. She will ask you "what's your goal from this" early on and maybe delay sleeping with you till she's sure you may be the deal.

To slowly open her up, we have a few good places in mind. Dance classes, jazz clubs, romantic parks, museums, and comedy clubs.

Here they are:

Just like comedy clubs, I don't prefer dinner dates early on because she's focusing on the food, not you. However, some women, especially cougars, love to brag about where their new date took them. If you sense that's your woman, then you can take her to any of these fancy restaurants in Chicago:

A Map of All the Best Cougar Dating Spots in Chicago

We combined all of Chicago's top cougar-friendly spots in just one map to save your time while cruising around the city. Use it, and let us know what happens next...

For more recommendations check out more great guides to meet cougars:

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