The 10 Proven Locations to Meet a Single Chicago MILF in 2019

Meet a Sexy Hot Chicago MILF

For young single guys, living in Chicago while on the lookout for a Chicago MILF can be especially rewarding. This classy city has great sites, fantastic restaurants, and plenty of places to check out while exploring. Chicago also has a well known and exciting online dating scene – an ideal place for guys to find sophisticated females.

There’s also a ton of locations to find the MILFs in Chicago that you’re seeking if you prefer in-person dating. We have all the best tips on where to find fun nights to drink, have exciting conversations and dance the night away with a lovely lady.

So where are the best places to visit to find sexy older women in Chicago?

The Top Notch Chicago MILF Spots That You Must Visit

Here are the 10 best venues to find MILFs in the Windy City.

Whole Foods Market is grocery shopping with plenty of MILFs in the aisles

Looking for a health conscious woman with great taste in men? Consider dropping by a whole foods store to find MILFs. Whole Foods Market is located throughout the city - Gold Coast, Streeterville, Lincoln Park, and South Loop.

Don’t miss out on some wonderful women by getting lazy and using Whole Food's online ordering. This market has tons of products, from pantry goods to fresh ingredients for dinner. Older women love Whole Foods because this grocer understands that life can be busy and health is a priority!

So consider driving by, parking your car and picking up a few items while you also get acquainted with its beautiful and single clientele.

You need to try Cougar Life to meet a lot of single Chicago MILF's quickly

For the guys who have super busy schedules, consider using an online dating tool to make things easier. We have not found a better way to meet a lot of attractive MILF's quickly and easily in Chicago.

Look to CougarLife.com – the best dating site for seeking out MILFs in Chicago (you can see what we mean for free with their free trial)! They are the best option we have found to meet single MILF's and there is no bigger site out there right now, especially if you are a younger guy (though it is great for older guys too).

A lot of single women in Chicago in their 30's and 40's have stopped going out and are only looking online. If you want to have the best chances possible you need to try online. We have tried out 100+ dating websites for finding older women, the #1 site for meeting a MILF we have found is Cougar Life.

Women this age are EXTREMELY busy and don't have a lot of time spend in the usual pickup spots. Instead, these women are looking online and you need to be where they are looking!

Try out Cougar Life's free trial and see what we are talking about.

Gibson’s Bar & Steakhouse is ideal to find yummy Chicago MILFs

Considered a Chicago steakhouse icon since opening its doors over 25 years ago, it’s also a prime spot to find MILFs. Open for lunch, dinner and patio dining, this steakhouse is only closed on major holidays. While Gibsons does not have a formal dress code, young men should know that they will not be permitted if wearing sleeveless shirts. So definitely come prepared with attractive gear if you hope to attract the attention of a Chicago MILF.

Patrons love this restaurant’s prime Angus beef, fresh fish, and uncompromising service. You can definitely impress an older woman who knows good local meat by frequenting this steakhouse, being that their angus is sourced from a carefully selected list of farms in the upper Midwest. Young men can stir the senses of a beautiful lady over classic cocktails or an offering from Gibson’s extensive wine list.

With three distinguished locations in Chicago, Rosemont, and Oak Brook, there are many opportunities to give their food, drinks and women a try.

When you just want to sleep around use Adult FriendFinder

Most guys assume that all the MILF's in Chicago are only looking for some kind of long-term relationship that could eventually turn into marriage. That couldn't be further from the truth. There is a huge portion of MILF's in the city that just want to have a good time with a guy, even just for one night. If that is the type of relationship you have mind you should try Adult FriendFinder.

There are a lot of great places to meet a Chicago MILF but they tend to be pretty spaced out. It can take a lot of time to go from the south side to Lincoln Park to Logan Square if those are the spots that are busy on a particular night. For guys who don't have the time or money to do that using a popular app like Adult FriendFinder makes the most sense.

We have had the best results finding MILF's for a little bedroom fun on AFF and it's pretty obvious why. They have the most active users in the city (60 million users total) and the most women over 30 using it of any app we have seen like this. All of those women are looking to meetup fast and are not going to be wasting your time.

Check them out for free and see what we mean with the links above. It's pretty fast and easy to get started.

Corcoran’s Grill & Pub offers happy times with drinks and flirting

For the Chicago Cubs baseball fans, Corcoran’s Grill & Pub is known as the spot to check out a game and an attractive woman if not at the stadium. This pub is also a long-running hangout for Iowa State college sports and Second City comedy fans. It’s well known for serving savory pub food and offering its clientele a cozy setting.

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While you’re on the lookout for that attractive lady, consider trying their bangers and mash specialty or the pub Burger with fried egg. An extra bonus is that they have tons of burger specials! Consider romancing that sexy single over some shareable appetizers, high-end salads, or alternatives to beef if she prefers healthier choices.

There is also plenty of draft and bottled beers, as well as cocktails and wines. Whether a fancy or casual choice of drinks and eats, you’re bound to impress in this laid-back locale.

Howl At The Moon is your venue for dancing the night away with a MILF

For the #1 nightlife spot with a plethora of MILFs in Chicago, visit Howl at the Moon. Part bar and part concert, this nightlife spot is well known for creating a non-stop party. Open from 5pm until 2 am, there’s plenty to do until closing time.

At this high-energy venue, young guys can enjoy talented musicians performing live while seeking out a sexy single. Once you find that older woman, enjoy the sounds of everything from Pop to Classic Rock to Hip Hop. Take her to the dance floor and sway your hips with a drink in hand.

This energetic and interactive setting is bound to create sizzling vibes between you.

Millennium Park is your outdoor spot for a leisurely walk with a MILF

Chicago outdoor spaces are ideal for those who love state-of-the-art architecture, landscape design and art. If you’re a young guy who loves culture and is seeking an older woman who shares this taste, try walking through Millennium Park.

In Millennium Park, you’ll find a new kind of town square. This space is a lively, spectacular gathering spot located in the heart of the city. Located in the Loop community area, this section features a variety of public art installations to experience with a sexy single lady.

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Take a pleasant stroll, or enjoy one another’s company while soaking up the afternoon sun. And if you’re visiting near the Christmas holiday, you can also check out the Christmas tree lighting.

The Lodge your tavern for meeting stimulating MILFs to dine with

Located at 21 W. Division St, this restaurant is a veritable Chicago landmark with plenty of sexy singles! Typically open from 2pm until 4 or 5am on every day of the week, this spot is an out-of-towners favorite for its cozy atmosphere.

Young guys can get to know a Chicago MILF while sharing conversation over the beer or liquor specials of the month. And if you arrive early, there are also great deals during Happy Hour.

From Monday to Friday between 4 and 7pm, patrons can enjoy a $4 beer or $5 liquor. This tavern is definitely one of the best venues to meet sexy singles while on a budget!

The Redhead Piano Bar combines nightlife with pianos and MILFs

Got a love for talented piano players and sexy single older women? Then you have to visit The Redhead, Chicago's Premier Piano Bar, located on bustling Ontario Street.

This bar is the perfect nightspot for fantastic upbeat music, lively conversation and meeting sophisticated ladies. This upscale venue attracts clientele from the suburbs to Lincoln Park, the Gold Coast to Wrigleyville, as well as visitors to Chicago.

With an exciting yet comfortable setting, young guys are sure to find women who enjoy the best nightlife has to offer. Seduce an attractive single amid walls lined with sheet music and famous movie stars of yesteryear.

This ambiance definitely helps create an atmosphere of congeniality and warmth that all couples will appreciate. Open nightly from 7pm - 4am, and Saturdays until 5am, this piano bar has gotten the finest of everything.

Ladies, premium liquor and fine cigars!

Hangge-Uppe is your basement jam with plenty of MILFs

Located in the heart of the Rush & Division nightlife scene, the Hangge-Uppe has been a staple of entertainment in Chicago for over 40 years. This bar consists of two floors, two all-request DJs and five fully staffed bars.

The upstairs level brings Top 40 beats to its clientele, while the basement rocks the oldies. Young guys can definitely count on this spot to get their hips moving along with any attractive lady they seduce. Females agree that this bar is the perfect spot to dance the night away.

Open from 9pm – 4am, and Saturday: 8pm – 5am, attendees can enjoy beer and liquor of the month specials. And if you arrive early, Hangee-Uppe also has a really great $6 all day special including no cover charge on Friday and Saturday nights.

ROOF on the Wit is your hotel bar that caters to upscale MILFs in Chicago

High above the city on the 27th floor is Chicago’s ROOF on the Wit. This contemporary and upscale hotel bar is one of the best bars to find a MILF.

With a strict dress code, you can be sure that the ladies you will find here are among Chicago’s classiest. Located within a contemporary 4-star hotel, ROOF is known for its awesome private events, great bites and sumptuous sips.

Open until 2am Monday through Friday, and until 3am on Saturdays, this high-energy bar is the perfect spot to get your dance on. And if it’s a sophisticated lady you’re searching for, you can bet that you’ll find her here waiting to be asked to dance.

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