Our 13 Favorite Places to Find a Single Illinois MILF for 2020

Attractive Illinois MILF

The state of Illinois is full of busy cities and residential suburban areas. And there are tons of great locations to find a MILF in Illinois.

These may not be obvious right away, though, because MILFs don’t hang out in the usual dating places. After all, Illinois has countless sizzling nightlife choices, beautiful local parks and delightful restaurants to wine and dine in. For some of these, younger women are the prime clientele. So you’ll hardly see any MILFs around.

When you’re looking for older ladies specifically, you’ll have to venture away from the standard recommendations. MILFs already have different tastes from women in their 20s and college students. So you’ll have a huge advantage if you know where the younger women don’t hang out.

Get ahead in your MILF search by visiting the hotspots that we’ve listed down below. Whether you’re more of a gym buff or you like hitting the nightclubs late, you can choose somewhere that you’re comfortable with. We’ve also included online dating options because it’s reliable in helping you connect with a gorgeous MILF in Illinois.

Ready to hit the MILF bars in Illinois and other high-probability destinations? Keep scrolling down and don’t forget to leave a comment once you’ve tried them out!

These Are The Must-Visit Venues for a MILF in Illinois

Now you’re on your way to meeting a compatible mature woman:

Row House amps up your fitness and dating game with sexy older women

Illinois MILFs on the rowing machines at Row House

@RowHouseLincolnPark

Located in Clybourn Ave., Chicago, Row House is a boutique fitness studio that’ll get you ahead in your MILF search. Many single MILFs searching for younger men love working out. Plus, the ladies here are toned and sexy.

The classes at Row House are based on rowing, giving you a cardio workout that’s full body but low-impact. Whether you’re already buff or looking to be more active, there’s a class here for you. You can go for a heavy adrenaline rush, focus on stretching or lift dumbbells for shredding.

Classes typically last for 45 mins, and the facilities are always incredibly clean. Because of their great workout concept, they’ve attracted plenty of loyal clients who work out here regularly.

To boost your chances of hitting it off with a MILF in Illinois, stay around after class and chat with the attractive older women there. While this branch at Lincoln Park is the most popular, Row House is also available at Old Town and Fulton Market, and there’s a Naperville branch too.

Adult FriendFinder lets you choose who you want to sleep with

Homepage for Adult Friend Finder

As men, we all understand the difficulty and awkwardness of trying to pick up an Illinois MILF in public. Rejection sucks and it can kill confidence easily. This is why the stakes are much lower when you give online dating a shot. But what site should you try if you’re looking for something casual and fun? In our experience, it’s Adult FriendFinder.

It’s hard NOT to recommend that guys at least check out Adult FriendFinder (you can try them for free with the links above after all). We have seen a lot of guys find success using it and most of those guys have been pretty average in the looks department. With that kind of success and how little time it takes to use there really isn’t a downside.

Sure, you can be choosy on other apps. But you might quickly run out of options. Adult FriendFinder is the largest app of its kind, so you won’t have that problem. With over 50 million members, you don’t have to worry about running out of people in your area after a few swipes. There are plenty of MILFs in Illinois to choose from here!

It is the perfect place to be picky and pursue the woman you really want. Plus, all the women on there are looking for more than a date, they are looking for something casual and physical. You can look for women on the way to work, during lunch, at the gym, while watching the big game. Anywhere and anytime. That’s how Adult FriendFinder gives you the most choices and the most chances. Sign up for their free trial and see what kind of women are in your area.

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We've tried out a lot of different sites and apps to meet MILFs and nothing has worked nearly as well as this site. You need to check out Adult FriendFinder's free trial with this link if you're serious about meeting women and want to stop wasting time. There isn't a faster or easier way to meet MILFs that actually want to meet up and head to the bedroom that we've found.

 

Indulge your cravings with a MILF at the North American Pizza and Culinary Academy

Dinnertime at the North American Pizza and Culinary Academy

@pizzaculinaryacademy

The North American Pizza and Culinary Academy is one of the only 20 pizza schools in the world. It attracts a wide range of people. That includes fans of Italian cuisine, chefs, your everyday foodie or simply anyone who loves pizza. Because of its reputation, it’s also a favorite among Chicago and Illinois MILFs looking for a fun way to spend their evening.

For wooing an older woman in a casual environment, we recommend attending any of their classes. Each class lasts for two hours, usually in the evening, and prices range from $50 to $150.

Demonstration classes are often like parties where you watch the chefs prepare the food while asking questions. These are great for socializing because you can go around the room, easily striking up a conversation with any of your MILF classmates.

Alternatively, try their hands-on classes if you’re feeling a little shy. You’ll be part of a group that’ll work together to create a recipe. This can give you more time to warm up to the older ladies there.

Either way, with the group dinner that follows after, you have plenty of opportunities to ensnare the attention of a MILF!

Cougar Life has consistently been the easiest way to meet single MILFs across Illinois (try it free)

cougarlife.com homepage image

There are a lot of great places on our list where you can meet attractive, single MILFs in Illinois. But you need to be smart about how you spend your time. Most guys only have a couple of days a week when they have the time to meet women. If that's the only time you can meet a MILF you're going to be leaving a lot of opportunities off the table.

There isn't a faster or easier way to meet single MILFs 24/7 than Cougar Life!

A lot of the single cougars in Illinois you are looking for have simply stopped spending time in bars and clubs because they prefer meeting guys online. They don't have the time either. It's also really hard to beat being able to meet other singles from the comfort of your couch. After trying out and ranking all the best apps and sites for meeting MILFs there are a few reasons Cougar Life's free trial delivers so well:

It works really well even outside of big cities

Most of the apps and sites out there for meeting MILFs don't work particularly well outside of city centers. For guys who are a little further out, these sites will just let you down. Cougar Life is different.

When you're specifically trying to meet a single MILF Cougar Life is going to have the most opportunities!

When you have a site that has over 7,000,000 active members and all of the women are single MILFs and more mature women, there will be lots of options for you. Dating is always a bit of a numbers game. So you want an option that can do this for you.

The MILFs here are really responsive compared to other sites/apps

If you've spent much time on other MILF dating apps and sites you know that many of them are filled with flakey women. They rarely respond. But when they do they tend to disappear after a couple of messages. Instead of looking for dates they just want attention and compliments from men.

With a specialized site like Cougar Life, you get to avoid most of the time-wasting women!

Since Cougar Life is so specific about who it's for, the vast majority of women who just want a compliment avoid it. They go to the larger, more general options where they can get the most attention possible. That means that the women on Cougar Life actually respond and actually show up for dates!

Younger guys get great results

Younger guys who are looking to date older MILFs have a tough road on other sites. A lot of women are too shy or embarrassed on larger sites to pursue younger guys. That makes it really tough to find them and get them to respond.

With Cougar Life EVERY SINGLE WOMAN is interested in both younger and older guys. This means you won't waste any time spending hours seeking one older woman looking for younger guys. Every woman you message is open to it!

You should give Cougar Life's free trial and see what we're talking about. It's a great option for most guys and it's really easy to get set up and running. Change your approach and get new results.

Have a romantic time out with an Illinois MILF at Lincoln Park

The pond at Lincoln Park

commons.wikimedia.org

Lincoln Park is a romantic, laidback spot in Chicago where you can comfortably get to know a MILF. It gets crowded here during the weekends because it provides a nice respite from the usual frenetic pace of the city.

Because there’s also a zoo and conservatory inside the park, MILFs often bring their kids here on the weekends. You won’t have a problem encountering attractive older ladies!

Nestled right at the heart of downtown, Lincoln Park is easily accessible, and there are tons of things you can do here. You can take your dog out for a walk, go biking along a picturesque trail, or simply sit down on a bench while enjoying ice cream from a food stall.

The park is also well-designed, with monuments and works of architecture like the Lincoln statue. In fact, if you’re here during the evening, it’s excellent for snagging a MILF in Illinois because it sets the mood with an enchanting skyline view of the city. Many proposal and engagement photos have been taken here, so you won’t be the first!

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Whole Foods Market offers MILF encounters and an upscale grocery experience

A charcuterie board with ingredients from Whole Foods Market

@wholefoodsmarket

Getting the attention of a mature woman doesn’t always have to take place in a formal setting. Think about it from the perspective of a woman who’s either heading towards her middle-aged years or has already arrived there. Aside from wanting to securing her financial future, beautiful MILFs also shop for food that may be healthier than what they munched on back in their 20s. When you're looking for great places to pick up more mature women Whole Foods is always a good start.

The Lincoln Park branch of Whole Foods Market should be on your list for meeting a wonderful older woman. You might find a fit and sexy MILF in this classy store while purchasing bread, surveying meat and seafood, or checking out bottles of wine.

Take the time to satisfy both your shopping needs and your dating needs, and give Whole Foods Market the chance to show an older woman that you can meet her at her maturity level.

RiverEdge Park is your public park for meeting fantastic MILFs

Lots of people waiting for a performance at RiverEdge Park

paramountaurora.com

The RiverEdge Park in Aurora is a wonderful outdoor space where you can look for a MILF in Illinois. This 8,500-seat concert venue is available year-round, with many performances appealing to that older female you’re hoping to have a romantic connection with.

After you settle down for parking, you can take a stroll along the river walk or cruise at a steady pace on your bicycle to survey the serene surroundings. Feel free to take in the lovely view from the pier while having a casual conversation with that smiling MILF who has been checking you out.

Gibsons Bar & Steakhouse is where you can satiate your appetite for older women

The outdoor patio area of Gibsons Bar & Steakhouse at night

@gibsonssteakhouse

When you’re looking to connect with an older lady while enjoying a much-talked-about piece of Prime Angus beef, Gibsons in Chicago is your choice among Illinois MILF bars.

Since 1989, Gibsons has attracted not just MILFs in search of hot younger guys, but also celebrities who have learned about its legendary reputation. When you want a great place to meet a MILF at a bar, high-quality steakhouses like this tend to be gold mines.

You and your new mature female friend can go home and brag about having some “USDA Gibsons Prime Angus Beef.” The Gibsons Restaurant Group is the first eatery in the United States to have its very own USDA Certified Angus Beef Program. Go have that prestigious meal with a choice from their impeccable wine list.

This will be an evening for you to make a great impact with flirty compliments and a dashing appearance. Keep in mind that Gibsons doesn’t permit sleeveless shirts. So opt for a sharper outfit like a blazer and jeans.

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Hangge-Uppe brings you a dive bar setting for fun flirting

Women hanging out at Hangge-Uppe

@TheHanggeUppe

To meet a sexy MILF in Illinois, be sure to make a stop at Hangge-Uppe, a dive club at 14 W. Elm Street. For over 40 years, this party spot has been a prevalent part of the Rush & Division area entertainment scene. You’ll stumble upon energetic, young-at-heart MILFs ready to meet a younger man who can handle their adrenaline.

There are two floors in this action-packed environment. It's where older women move their bodies to the beats of two all-request DJs. You will have no problem offering a drink to one of those lovely ladies, thanks to Hangge-Uppe’s five fully staffed bars. Alternatively, you can make your way upstairs to pull off your own moves while you gyrate to some Top 40 tunes. In the basement, you’re sure to find some MILFs reminiscing to their earlier days, as the throwback tracks are in full effect down there.

State and Lake Chicago Tavern is for spicy bar action at The Wit Hotel

A laidback crowd at State and Lake Chicago Tavern

@StateandLakeChicagoTavern

This stylish hotel restaurant merges the pub flavor enjoyed by young craft beer connoisseurs with the sophistication that older women enjoy in a top-notch American wine list. State and Lake Chicago Tavern is located at The Wit hotel on 201 N State St, Chicago. Impress the upscale female customers with your appreciation of the menu, which offers fine cuisine from award-winning chefs. You can mingle with the overflow of lovely MILFS hanging out in the theater district after a show.

Industry leader Restaurant Hospitality has previously stated that State and Lake Chicago Tavern has the “Best Cocktails in America.” Have a drink on the roof and allow the glow of the evening skyline to illuminate your appearance while you catch a warm smile from a beautiful older woman. Bring your “A-Game” as you approach the lady catching your eye.

Bar DeVille is the lounge for meeting a MILF in Illinois

The romantically lit Bar DeVille

heislerhospitality.com

This West Town neighborhood bar is at 701 N. Damen Avenue on the corner of Damen and Huron.

Older ladies come here to enjoy classic cocktails at the art deco bar with its comfortable booth seating. You can also put your powers of flirting to work in the middle area, which has a pool table and more of a lounge feel to it. The backroom also offers a third option to meet tantalizing MILFs with its live entertainment and weekly comedy series.

Bar DeVille has respect from not just the locals, but also from its industry. It was awarded one of Food & Wine's “Top 100 Bars” in 2011 and 2012, and it’s also among the best Illinois MILF bars. Keep in mind that this lovely lounge is “cash only.” So be sure to have some cash instead of plastic in your wallet.

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Jonah’s Seafood House is where you can enjoy a marvelous meal with MILFs

The wooden exterior of Jonah’s Seafood House

@jonahsseafood

Jonah’s Seafood House at Peoria has built up its reputation as a special fine dining environment near the Illinois River. Local MILFs can dine on the fresh seafood flown in for the restaurant daily. The menu is adjusted regularly to reflect the new fish-related catch of the day. Meet mature women who fulfill your high standards while delighting in chicken, prime meats and shellfish.

With the wooden, rustic interior and ornate drink selections at their wine bar, you can relax and meet plenty of beautiful, classy Illinois MILFs.

Kingston Mines is the right nightclub for finding a MILF in Illinois

The stage at Kingston Mines

@kingstonmineschicago

Music has a way of striking up a romantic mood. The same applies to older women when they are in the presence of some jazz and blues tunes. To meet those lovely ladies who can appreciate sophisticated music, go to Kingston Mines in Chicago.

Music lovers can enjoy the festivities from the club’s two stages with rotating musical acts. You can in different areas to make a grand first impression on the different women you’ll meet.

Satiate your appetite with their french fries, burgers, ribs and fried okra, prepared with a Southern twist. The blackened catfish is also a great choice to refuel your energy level as you prepare to shake your body with a lively MILF.

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