best places to meet singles in chicago, illinoisSo what are the best places to meet singles in Chicago, IL?

There’s plenty of ways to meet new people in 2020 – both online and offline – believe it or not.

So, here’s our 9 ideas, ways and places to meet Chicago singles:

1. Best dating sites for Chicago singles? (forget Tinder!)

Tried Tinder? Got frustrated?

No wonder, Tinder has become more of a “game” than a dating platform to find normal conversations and finding dates.

chicago singlesBut, in 2020, it’s the good old dating sites where the magic happens.

Especially for professional singles in Chicago, Datermeister would recommend (if you’re around 30 or over). It’s a perfect alternative for the shallow atmosphere of Tinder.

Or go have a look at our 10 best dating sites in the USA list.

2. Best nightclubs to meet singles in Chicago?

Clubs aren’t usually the best places to strike up conversations but they’re still better than watching Netflix at home. Right?

Here’s a few clubs in Chicago that are good for singles:

PRYSM Nightclub (1543 N Kingsbury St): Prysm in Lincoln Park draws a big crowd of EDM fans especially on Saturday nights. Big name DJ’s, VIP bottle service + 3 different bars.

Berlin (954 W Belmont Ave): for the hipster type who wants to dance, drink and meet new people. Also the drink prices are very affordable.

East Room (2354 N Milwaukee Ave): a cool bar/nightclub with different themed nights 7 days a week. Mostly craft beers & whiskey on menu!

3. Best singles bars in Chicago (also 30+ singles)

If you’re not into the loud nightclub scene, there are plenty of good bars for singles in Chicago. Also you’ll usually find the late 20s singles and over 30-year-olds in bars rather than clubs.

Here’s a couple of spots for you:

Old Town Pour House (1419 N Wells St): especially if you’re a woman and you’re into bearded beer hipsters, this is your location. Good food, over 90 different beers to try and a sophisticated crowd (with plenty of singles as well)!

The Irish Oak (3511 N Clark St): a good laid back bar which has been proven to be a good place to get laid in Chicago.

Or just take a wingwoman or man with you and head to Division Street where you can do some serious bar hopping.. one drink here, one there while being open for meeting new people.

4. Live music events, stand up comedy shows = great places to meet singles in Chicago

Many busy singles just don’t have the time or interest to stand around in bars every weekend. But they enjoy going out to see their favorite artists and performers. Therefore live music events and stand up comedy shows are one of the best places to meet singles in Chicago who share your sense of humor or music taste.

Think about it. On a stand up comedy night there’s often alcohol involved and people are loosened up with (hopefully good) jokes. Perfect grounds for striking up conversations with new people.

Or when your favorite band or artist is playing, you have a concert hall full of your soul mates (at least in regards of your music taste).

5. Start going to the gym, yoga, meditation (or other social fitness hobby)

This tip is actually backed by science:

When we humans see familiar things on a regular basis, we start to like them more. This could apply to advertising but also to seeing the same faces on a regular basis.

It’s called the mere exposure effect. So when you see the same people at the gym every week, you (subconsciously) start liking them more, and vice versa. Then it’s easy to just say “hi” and even start small talk.. And you know the rest. Picking up women or men at the gym is a slow game so just take it easy, keep your eyes and ears open and see what happens.

Pretty much all Chicago singles in their 20s and 30s go to the gym, yoga, meditation or similar type of “social” fitness related hobby. So it’s a good idea to get active in this area as well.

And of course there’s the main benefit: you get fitter and healthier! When you’re single, you need a good level of self confidence if you want to find someone. When your body gets fit, your mind gets fit too!

6. Speed dating and other singles events in Chicago

If you feel that normal online dating is not very time efficient, in speed dating you can meet several Chicago singles on one night:

..there’s even a book called “Blink” by Malcolm Gladwell where he speaks how we humans make pretty good decisions in a blink of an eye. Point being: you can get a pretty good idea if there is chemistry between you and your speed date partner in just a few minutes. You won’t have to waste time in first chatting online for couple weeks, setting up a date for another week, then either one cancels, and then 1 month later, you finally make it on the first date but there’s no chemistry whatsoever.

You can find some speed dating events in Chicago through Eventbrite.

7. Other meet ups and networking events to meet new people in Chicago?

If you don’t feel comfortable going to singles events, just go to any networking events which are about topics you are interested in. They are packed with Chicago singles who don’t want to “identify” as single by going to “singles only” events.

You can find tons of interesting groups on or some local Facebook groups.

Expanding your social circles is definitely a good idea now that you are single. Still today, in 2020, most couples have met through common friends or acquaintances. It’s always nice to find new friends and even better if you find the love of your life among or through them.

8. New intellectual hobby – learning a new language etc..

meet singles in chicagoHave you thought about learning a new language?

Attend a language course. Or find a language tandem partner. There’s plenty of international students and professionals in Chicago who would love to fine tune their English with you. And in exchange you could learn their mother tongue. And who knows if you end up speaking the language of love later on..?

Or how about learning how to paint or other art related things? Just pick a hobby or course where there are other people involved too – you want to meet like minded people!

9. Cold approaching on the streets or supermarkets?

You might have had those moments in the streets or supermarkets when you see someone really gorgeous and interesting. But there’s no way you would dare to approach them?

A “soft” way to approach random people on the streets of Chicago is to just ask them a neutral question. Such as asking for a nice place to have lunch in the area, or a cafe to get some work done on the laptop, or just asking for the time (your phone battery is “dead”).

It’s all about getting that fear out of your head of approaching strangers.. You just have to practice and get comfortable with it. Repetitions, repetitions..


If you want to get rid of your single status, here’s a quote for you:

“If you always do what you’ve always done, you’ll always get what you’ve always got.”

So if you feel like your life is revolving around the same routines, hobbies and people – it’s time to go outside your comfort zone. Get active with new hobbies, try some dating sites and apps other than Tinder and go to any kind of networking events. And if you’re around 30 and well educated and/or career oriented, try – it’s the hottest dating site in Chicago in 2020.

And now:

What are the best places to meet singles in Chicago in your experience/opinion? Comment below!


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