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!
We're going to start things off with our favorite cougar bar in town. When you're just starting off try out:
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.
More and more mature women turn to online dating when it comes to meeting men for dates or casual flings. These two sites are where we often find them.
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 Adult FriendFinder is a great place to find them.
Adult FriendFinder 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 Adult FriendFinder 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 Adult FriendFinder 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 Adult FriendFinder!
When it comes to meeting a lot of cougars quickly, especially those interested in dating younger guys, there isn't a better option than Cougar Life (which just so happens to have a free trial). 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 Cougar Life 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 Cougar Life does. There are a few reasons this Chicago cougar dating site works so well:
There are more popular apps and sites out there but they just don't have the cougars. Cougar Life has over 7 million active members and EVERY SINGLE WOMAN on this site is a cougar. 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!
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 Cougar Life 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.
Cougar Life 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.
If you haven't tried it out yet give Cougar Life's free 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).
No list of places to meet cougars will be complete without a list of bars to check out. So drink, dance and socialize at these spots!
Downtown is full of great bars ranging from upscale establishments to more laidback hangouts. Take your pick from this list of cougars bars we enjoy.
The Lodge is on the city's famous nightclub strip, Rush & Division St. Cougars who want to party flock to this well-known late-night hotspot. This historic and popular venue first opened its doors in 1957. Since then, it has maintained its distinctly retro feel.
It attracts an older business crowd who come to the bar after work to have meetings and unwind, enjoying a drink or two. When the drinks start flowing and the jukebox booms, this is the place to visit It’s well-known amongst young men 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. Head there on a Saturday night, and you can take advantage of the later opening hours.
Debonair Social Club is one of the last standing nightclubs in Wicker Park. The nightclub is particularly popular for its two-floor operations. You can indulge in a lot of fun when you have the option of choosing two different floors to party on. Both floors draw in different crowds because they both play different music styles.
You’ll quickly notice that the nightclub attracts lots of single cougars. Since the club is fun with reasonably priced drinks, the club often gets pretty filled up. If you’re smart, then you’ll quickly take advantage of this. Grab a drink and then find a dance partner on the dancefloor. You could easily be walking away with someone hot in just a few hours.
Don't feel like heading to the center of town to meet the cougar of your dreams? These bars are away from the crowded city center but they're still popular among hot older women!
Delilah’s has been around since the early 90s and for good reason. The bar has an old school punk rock feel that attracts a super cool crowd. The women who come here to drink are always ready to party hard. We’ve only had the most stellar interactions with those who come here to listen to great music while grabbing a drink.
You’ll quickly notice that the DJs here are always spinning a wide variety of tunes. Whether you’re into rock & roll, punk rock, reggae, soul, or R&B, you’ll find music to dance to here. The bar has over 1000 beer and spirit options, so be prepared to indulge. Between special events and art openings, the crowd here is always ready to mingle and have fun.
For an authentic blues experience and cougars with great taste in music, BLUES is your destination for the night. This hole-in-the-wall joint reliably plays some of the best bar music in the city. It’s as dive-y as you can get, so the space is small and intimate. It’s best to arrive early if you’re looking to grab a seat! But there’s a porch area and a short bar to choose from.
Wherever you sit, you’ll bump elbows with people, and you’re bound to make new friends. Clients tend to be friendly, connecting easily through a shared love for music. You won’t have to worry about stretching yourself out to chat with a cougar. She might even approach you first, and the two of you can enjoy the beat together.
Although there’s a small cover charge, the drinks consist mostly of cheap beer and cocktails. You won’t be breaking the bank here. After all, the focus is on the live music—and the hot cougar you’ll hopefully be cozying up with.
Richard’s Bar is one of the few cougar bars in Chicago where you can smoke and down a cocktail at the same time. During evenings, there are cougars lurking in every corner. As long as you don’t mind cigarette smoke, you’ll have a grand time here where the cougar of your dreams might be waiting for you.
Cougars also tend to be huge fans of the décor at Richard’s. It hasn’t been redone in 40 years, retaining an authentic old-school vibe. The walls are teeming with vintage photos and posters, and they even have neon beer signs. Music comes from a jukebox that often plays tunes by Frank Sinatra and Dean Martin. How’s that for romantic?
You’ll feel like you’ve stepped into another era. The conversation is easy too because of the small space. The bar can hold around a dozen people, and the rest sit on the five or six tables nearby.
They don’t have beer on tap, but the drinks are strong and affordable, starting at $3. With such an atmospheric setting, you can hang around near a cute cougar and flirt naturally.
Party all night long and show off your dance moves at these cougar bars! What better way to meet a sexy older woman than by bumping and grinding on the dance floor?
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 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.
This is one of the most famed Chicago cougar bars, and it makes no secret of being so. While other establishments may obviously attract cougars, Howl at the Moon goes one step further and flaunts itself as a hangout for cougars.
Howl at the Moon holds a cougar night every Thursday. The bar is packed then with groups of mature ladies seeking younger men, along with twenty-something guys eager to bag a cougar in turn. They’re also eager to get down and dirty on the dance floor. The competition here can be stiff because it’s so obviously advertised, so be ready to pull out all the stops.
Who says you can only meet hot cougars at bars and clubs? Our city has so many daytime hotspots where you can meet hot single women!
If you prefer to do your Chicago cougar hunting in the daytime, you may be surprised to hear that you can pick up a cougar by simply heading to your local park. Spots such as the Millennium Park, Grant Park and Lincoln Park are all nice to take a pleasant stroll in. You’re likely to meet cougars who enjoy the fresh air too.
Whether they’re looking to stretch their legs, read a book, walk their dogs or soak up the afternoon sun, cougars love hanging out at parks. Put on your walking shoes on and prepare to strike up a conversation!
The Miller Lite Beer Garden is an awesome spot to head out to if you’re looking for a fun time. The beer garden is located outside on the East End of the Navy Pier. The outdoor destination makes it the perfect spot to grab a drink during the warmer months. Lots of single women head out here to drink, eat and hang out with their friends.
What makes this spot so great is that it’s the perfect mix of a restaurant, beer garden and concert venue. You can catch some pretty great live music acts here while enjoying a delicious beer out by the water. Women love coming here for the view, so you’ll notice quickly just how many women come here. So be brave and introduce yourself to someone new who could be looking for a one-night fling.
A mature lady likes to fill her time doing interesting things. This can include learning a new skill. A language class may not be the first place that comes to mind when thinking about meeting a classy older lady, but you’ll actually find a lot there!
If you are interested in learning a new language or brushing up on your language skills, taking a class could have you meet the cougar of your dreams. Language Loop, the Latin American Language Center and the Berlitz Learning Center all offer courses.
Even if you don’t end up meeting someone, there is nothing sexier to cougars than a younger man who can speak another language. You can then use your newfound skills to impress them when out and about too.
In case you need a few more options for meeting older women in the city, here are some more spots where we always find them.
Hate striking out on the dance floor of your favorite nightclub? Then you’ll want to consider taking some dance courses. Luckily, a local dance studio is one of the best places to meet single cougars. Chicago Dance is a dance studio that offers both group and private Latin and ballroom dance lessons to dancers of all levels.
Since you’ll be swapping partners throughout the dance lesson, it gives you the perfect opportunity to chat up lots of women. So if you don’t click with the first woman, you’ll have a new opportunity in a few minutes. You’ll be killing two birds with one stone by learning some great dance moves while meeting lots of interested women.
If you haven't noticed, finding single cougars in the usual spots around the city has been getting more difficult. A lot of women are only looking online these days (especially those interested in something more than a fling).
eHarmony (which you can try for it now right here) is the best online dating site for helping guys find attractive older women to chat to, meet up with and date in our extensive experience. We spend hundreds and hundreds of hours every year to find the best sites and apps for finding and meeting cougars. eHarmony has consistently been at the top and is the first app you should try.
Meet cougars in Chicago by signing up to this site, so when you join you can easily browse the profiles of these attractive older ladies and get to know them. They have the most women 35+ using it and the women on this site are actually motivated to respond. You don't get women just looking for an ego boost here. Their signup process is a bit longer but that does a fantastic job of filtering out all the women who aren't committed to actually responding to messages and meeting guys.
This site has the most responsive women we have seen anywhere if you only want a long-term relationship!
eHarmony is the perfect place to start if you are searching for cougars in the city, especially if you are thinking more long-term. Meeting fun, interesting older women doesn't get any quicker or easier. If you don't have a lot of time to spend in a bar or club this should be your first stop.
Check out their proven trial and let us know how it went.
If you’re looking for a low-key place to flirt and meet cougars in Chicago, then Sawada Coffee is a great option. Many guys overlook just how great a coffee shop’s atmosphere is for starting up a conversation. This quaint coffee shop makes it even easier with its cozy decor and amazing coffee drinks.
Sawada Coffee is a place where lots of locals come to grab a coffee, relax and play a game of ping-pong. The atmosphere is pretty chill and you’ll immediately notice that none of the women have their guard up. That means you’ll have much better luck striking up a conversation here.
For more recommendations check out more great guides to meet cougars: