15 Greatest Places And Bars To Find Cougars In Chicago for 2019

Chicago cougar sipping wine by a windowIf you are interested in meeting cougars in Chicago you are in for a treat. We have put together a list of our favorite spots in the city where we have had the best success meeting single cougars (not just in the Viagra Triangle). 

If you have not had a lot of luck meeting any Chicago cougars so far these are the places you need to be spending your time. The city is full of energy and bursting with singles looking to meet up if you know the Chicago cougar bars and other spots that deliver.

Where To Find Cougars In Chicago

There are plenty of spots in the city where you can find Cougars in Chicago, so read on to find out where they are.

Howl at the Moon is one of the best Chicago cougar bars

This is one of the most famed Cougar bars in Chicago and makes no secret of being so. While other establishments may obviously attract the Cougars, not as many flaunt themselves as being a venue exclusively for such.

However, Howl at the Moon holds a Cougar night each week on a Thursday which sees groups of more mature ladies seeking younger men, and twenty-something men eager to bag a Cougar pack this bar out, neck $5 cosmos and get down and dirty on the dance floor. Be warned, because it is so obviously advertised, there is stiff competition here, so be ready to pull out all the stops.

Cougar Life is the fastest and easiest way to meet Chicago cougars

If you have not noticed, finding single cougars in the usual spots around Chicago has been getting more difficult. A lot of women are only looking online these days (especially those interested in younger guys).

Cougar Life (which you can try for free here) is the best online dating site for helping guys find attractive older women to chat to, meet up with, and date. Many Cougars in Chicago are signed up to the site, so if you join (which is free of charge) you can browse the profiles of these attractive older ladies and get to know them.

Cougar Life is the perfect place to start if you are searching for Cougars in the city in fact, they were our top-rated cougar dating site for Chicago. Meeting fun, interesting older women doesn't get any quicker any easier if you don't have a lot of time to spend in a bar or club.

Check out their free trial and let us know how it went.

The Wild Hare 

This relaxed bar is a little known Chicago Cougar bar. Cougars flock here each and every week to sip on rum and listen to some live music. Get out there on the dance floor and bust some moves to impress the ladies, or why not sit in one of the secluded corners and share a plate of some delicious Caribbean fare?

If you are just looking for someone to warm up your bed use Adult FriendFinder

Not every Chicago cougar is looking for a real relationship. A lot of them just want to find a guy for some fun without any complications. From what we have seen, most of those women are on Adult FriendFinder.

We don’t recommend many site or apps for guys who are just looking for sex but when we do it’s usually Adult FriendFinder. We have just seen so many more guys find what they are looking for compared to the other options out there that it’s hard to recommend another app. Sure, it isn’t perfect, but it’s the best option for most guys out there right now.

Sure, Tinder is great if you want to date a younger woman, but very few women over 30 are using it. For whatever reason Adult FriendFinder is way more comfortable for them to use and therefore much easier to find them on. Having 60 million members certainly helps though!

Give their free trial a shot and see the quality of cougars in Chicago that are in your neighborhood. Gold Coast is kinda ridiculous.

When you are looking for cougars online it's always a numbers game so you want to go with the app that gives you the most options. Send out a few messages and see where things go along with a little time spent in the other solid spots for Chicago hookups.

Dance classes are great for finding cougars in Chicago

Dance classes are a fantastic way to meet an older lady. Cougars tend to have a wide variety of interests and many will have hobbies such as dancing which they enjoy as it keeps them fit and are a fun way of meeting new people.

If you prefer a more low key setting rather then battling it out with the competition in a noisy bar or club then dance classes could be exactly the right situation for you. Here you can get close, have a one on one conversation, and impress her with your awesome dance moves.

Chicago cougars and cubs speed dating is a thing

Cougars and Cubs Speed Dating in Chicago are a series of events specifically designed to get young men and more mature ladies together. There are events held all over the city and these are a perfect way to dip your tow in the dating pool and see what is out there for you.

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Cougars and Cubs Speed Dating have their own website so you can simply log on and find out when the next event is taking place. If there aren’t any upcoming events you can even email them to request one and they will do their best to help you out. Fun nights of drinks, good conversation and dancing are what they are all about and it is a fantastic way to get straight in there and meet the older lady you have been looking for!


If you prefer to do your Chicago cougar hunting out and about in the daytime, you may be surprised to hear that simply heading to your local park can be a great place to pick up a Chicago Cougar. Spots such as the Millennium Park, Grant Park and Lincoln Park are all nice to take a pleasant stroll in, and it is more than likely if you do, that you will find many Cougars doing the same.

Whether it is to stretch their legs, read a book, or soak up the afternoon sun, parks are a hotspot for Cougars so get your walking shoes on and be prepared to be bold, and strike up a conversation.


Restaurants are great places to pick up a more mature lady. Head to classy, all-American dining establishments and you will easily be able to spot a Cougar, either sipping a cocktail at the bar, or perhaps dining alone with a book.

Language classes

A more mature lady likes to fill her time doing interesting things, and this perhaps includes learning a new skill. A language class may not be the first place that springs to mind when thinking about meeting a classy older lady, but actually it is a pretty good place.

Beyondages.com video course

If you are interested in learning a new language, or brushing up on your language skills, taking a class could see you meet the Cougar of your dreams. Language Loop, the Adult Education Centre and the Berlitz Chicago Learning Center all offer courses.

Even if you don’t end up meeting someone, there is nothing sexier to Chicago cougars than a younger man who can speak another language, so you can use your new found skills to impress them when out and about too.

Shopping malls

High end, luxury malls are a fantastic place to spot a refined, mature lady doing a spot of shopping. Chicago Cougars tend to flock to the mile-long stretch of North Michigan Avenue between Oak Street and the Chicago River which is otherwise known as the “magnificent mile” due to its vast array of upmarket and designer shops.


If you are hoping to bag a top-class Chicago Cougar, you need to stay in shape. Cougars in Chicago are impressed by a fit and toned physique of a young man who clearly looks after himself. Health and fitness is extremely important to these attractive older ladies and so if you head down to the gym you will almost certainly find them working out to keep themselves in top condition. Get pumping those weights and you will be sure to catch their eye.

Art galleries

Older ladies tend to enjoy the arts and cultural scene and know a lot about it as well. If you want to search for a Chicago Cougar during the day then why not head to an art gallery or museum?

The renowned Museum Campus along Lake Michigan is a great place to start and where you can find the Adler Planetarium & Astronomy Museum, The Field Museum, and The Shedd Aquarium.

The Art Institute of Chicago is another superb venue where cultured and intelligent Cougars like to gather.

Sports clubs

Taking up a social sport is another fantastic way to meet Cougars in Chicago. Playing tennis, squash or any other team or social sport is a great way to meet an older lady. You can impress with your skills, and improve your fitness at the same time. Try the Chicago Sport & Social Club, or Lakeshore Sport & Fitness Lincoln Park and you might well find exactly what you are looking for.

The Chicago Cougar Bars You Need To Try

So if you are on the hunt for a classy Cougar then read on to discover some of the best places to go to meet them.

The online dating scene in Chicago is also fun and fast-paced (we even put together a review of the best dating sites for cougars in Chicago) and those looking to meet a Cougar will find plenty of opportunities.

The Lodge

The Lodge can be found on Chicago’s famous nightclub strip -Rush & Division St. This well known late night hotspot is where all those who are looking for a party flock to of an evening to let down their hair, and enjoy a drink or two. The Lodge is a historic and popular venue, first opening its doors in 1957, and it maintains its distinctly retro feel.

It attracts an older business crowd who come to the bar after work to have meetings and unwind. When the drinks get flowing and the jukebox booms, this is the place to come to party, and is well known amongst the hunters as being one of the top Chicago Cougar bars in the city.

Professional, well to do ladies will be putty in your hands if you play your cards right, and if you head there on a Saturday night you can take advantage of the later opening hours.

The Redhead Piano Bar 

The Readhead Piano Bar is one of the more upscale Chicago cougar bars that is fantastic if you are looking to meet a sophisticated older lady. You can get ahead of the competition in this Chicago Cougar bar by dressing to impress. Make sure you bring you A game here, the bouncers won’t let anyone past the door that they deem to be unworthy, and with a strict dress code it is worth getting it right.

The Green Mill 

This is one of the liveliest Cougar bars in Chicago. If you prefer a more manly venue to do your hunting, the Green Mill will be right up your street. Kitted out as a speakeasy you can sip on strong liquor and listen to some live jazz or swing music. Classy cougars favor this joint so be ready to get your charm on.

Nacional 27 

A great venue to meet a more mature lady, Nacional 27 hosts a variety of dance nights throughout the week and the Eat, Drink and Dance weekend nights are certainly worth a visit. On Wednesday head here for complimentary Salsa lessons where you can get a little sweaty and learn some new moves with your Cougar dance partner, or simply learn how to swing those hips and return on the weekend to impress all the ladies.


This vibrant club can be found in the heart of the Rush & Division strip. This club has plenty of history, having first opened its doors over 40 years ago. With 2 floors, two DJ’s and not less than 5 bustling bars you can drink and dance until you drop, which sees the Cougars flock to it from all over the city.

POPS for champagne

If you are looking for one of the more elegant Chicago Cougar bars head to the classy POPS for champagne. With sophistication oozing from every corner you can sip on champagne and cocktails all evening while listening to live jazz. Don a shirt and blazer and make intelligent conversation and you are sure to make the Cougars melt.

The Bar at The Peninsula 

The only bigger attraction than a young man to a Cougar is a well-made martini, and nowhere does it better than the Bar at The Peninsula. This Chicago Cougar bar attracts a well to do, beautiful crowd. Come early to find plenty of Cougars taking a load off after a long days shopping on nearby Michigan Avenue.

Kirkwood bar and grill 

A fun and lively place this Cougar bar in Chicago has more of a relaxed vibe. if you are looking for something a little more low key where you can enjoy your huge fishbowl cocktail in a massive beer garden then this is the place to head to.

Decent food is also on offer, and there are 29 (yes 29!) plasmas showing different sporting events throughout the week. Remember Cougars are on the lookout too, so sports bars are often there destination of choice when searching for a little fun.

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