Tinder Chicago: How to Get Lucky on Dating Apps in Chicago

You’re probably passing through or moving to Chicago.

Or you’re a local dipping a toe into the Chicago digital dating scene.

And all you want to know is the best app or website to meet sexy singles.

Is Tinder best for Chicago? And what are some pro tips to go about this?

Well, stay put.

You’re going to get:

  • The best dating apps in Chicago to get 3 dates a week
  • An unknown Chicago swiping spot that doubles your matches
  • 7 Best Tinder date locations
  • My secret opener that’s guaranteed to get you a reply
  • The #1 TextGod principle to keeping her interested through text
  • All the dating DO’s and DON’Ts of Tindering in Chicago
  • And much more…

Important: I know you're sometimes unsure what to text. So I've put together 10 Texts That Always Work. Copy-paste lines that instantly attract her and make her crave your attention. They work and they are free. Just a small gift to get you started. Enjoy! Click here to get them.

#1: Most popular dating apps in Chicago

You’re about to get what app is best for meeting girls online in Chicago.

Even though Tinder has the largest audience across America as a whole (8.54 million users), the swiping app has not captured the entire dating market.

Match, Bumble, Plenty of Fish, Hinge and OKCupid are contenders too. To name a few.

Especially Bumble is quite popular in Chicago.

But when it comes to dating tools, Illinois has one clear reigning champion: Tinder.

Chicago is actually one of the three cities with the most active Tinder users in the US.

And not just because Chi-Town is one of the most populous of the country, but because it’s the home of many highly educated professionals.

And the highly educated usually hit pause on marriage and kids, because they’re busy climbing the career ladder.

Millennials are most likely to get married at the age of 40.

So there’s an abundance of people ready to go on a date or two(thousand).

In short, Chicago is filled with ambitious women looking for a good, baby-free time.

Sorry, kiddo.

Before all you romantic dudes run off scared, when I say ‘good time’, I mean that in the (Text)God honoring way.

You’ll meet girls on Tinder who want to get laid on Tinder and those who are looking to get married through Tinder.

That being said, other dating apps are worth giving a shot too.

A large chunk of 30+ aged women in Chicago are single and ready to mingle. If that’s your thing, check out Cougar Life.

If you’re a college graduate looking for someone else who has also spent years on earning a piece of paper, consider Elite Singles.

#2: Who are you going to meet on Chicago Tinder?

You’re about to discover if Tinder Chicago has the right women for you.

Sure Chicago has one of the largest groups of Tinder users, but who are you likely to talk with?

Is it a sausage fest fighting over a couple of peaches?

Is the Chicago scene filled with shady catfish?

Or does the Windy city get its name from spunky grannies who can’t keep their legs closed?

When she’s thinking of that hot load of brogurt you splooged in her face.

Chicago’s Tinder population is so large you’ll find just about anyone.

But with so many universities in town, the majority of the ladies on Tinder will be students or college graduates between the ages of 18 and 30.

A quick aside, if you’re not going to stay in Chicago for long, consider swiping in and around Old Town. That neighborhood is known for handing out right swipes like 14th century rats did the plague.

So if you want to increase your matches, visit Old Town.

#3: What to send to your new Chicago Tinder match

You’re about to get the Tinder opener that will make her feel special and get you a reply.


It’s a match!

Time to sweep her off her feet, but all you can think of to say is:


Thank the TextGod you closed Tinder and are reading this article. Because I’m going to give you some lines that are guaranteed to get you a reply.

Let me explain the basics of texting first, in case you ever want to create your own material.

Most important rule: don’t be generic.


Well, there’s no demand for it.

Your Tinder competitors have already flooded the market with boring.

If you want to grab her attention, you need to be different.

Make way for the contextual opener:

I’m about to get deep dish pizza. Join me so we can be in a food coma together.

Or if you want to make it slightly more over the top:

I’m about to get deep dish pizza. Join me because I’m too selfish to be the only one suffering food coma.

If you’re out of the know, Chicagoans bake their pizzas in dishes so it resembles a pie.

What makes this line so good?

It’s original. She hasn’t seen it before.

It’s anything but bland.

And even if she rejects your offer for pizza, you painted an image of the two of you on a date.

So if she continues to talk to you, she’s definitely hinting she’s willing to go on a date later down the line.

You must be why they call this the Windy City, because you’re blowing me away.

#4: Moving from texting to dating

You’re about to find out what the average Joe does wrong when asking her out, so you can do it right!

You see, the average Joe doesn’t ask her out because he feels like he hasn’t been Tinder texting long enough.


The road to the date doesn’t have to be long. In fact, the method I’m about to give you makes setting up the date quick and easy.

But before I hand you the shortcut to dating Shangri-La, we have to take a look at the most  common Tinder mistakes.

The average duderino’s conversation dies out faster than the careers from the dudes that did Macarena.

If only we knew why.

By some miracle I do. And it doesn’t involve crossing your hands behind your head and gyrating your hips.

The truth is far more boring.

You see, any guy can grab a woman’s interest with a brilliant line they found on the internet.

But the real magic comes after the opener. And there are no copypasta lines for that.

So after firing the killer opener, guys have to rely on their own wit. And usually it’s about as sharp as a wet sponge.

What do you do for work?

Do you have any siblings?

What are your hobbies?

If you’re real quiet, you can hear her panties getting wet.

*coughs up lung*

Excuse me. I meant to say:

If you’re quiet, you can hear her reaching for her gun.

Her: One more question! I dare you!

Every line makes her hate you a little bit more.

Not because she’s evil, but because she’s on Tinder for fun and you’re turning the conversation into an interview.

Which is fine, if you’re hiring. But not when you’re flirting.

If you want to make her crazy about you, follow the TextGod texting rule:

Spark her every emotion, except boredom.

Instead of blowing her brains out, you hand out small doses of pure emotion. Each different from the one before.

And before you know it, she’s hooked. And she’s craving for more.

She can’t stop herself from replying to your messages, because she needs a new hit from your emotional crack pipe.

So how do we lace your texts with emotion?

Let’s start with the questions of the Basic Bro.

Rather than asking, fill in the blanks.

Do you want to know what her hobbies are? Take a guess.

I’m not sure why, but I get the feeling you’re a tv series binge watcher. On such a scale that you’re not afraid of spending half a day in bed sometimes when you should actually be doing stuff.

Feel like asking her where she’s from? Go out on a limb.

You’re definitely a country girl. Just by looking at your boots I can tell you own a horse, know how to drive a tractor, and have a rifle hanging above your bed.

Not only are you going to figure out the truth, people love to correct others when they are wrong, you’re also lighting up her emotions.

Looking at both lines, you can tell they have a teasing and humorous tone.

But only teasing isn’t enough to hold her interest. If she knows what’s coming next, she’s going to get bored.

To keep her engaged, you have to be unpredictable.

Use the TextGod TLC-formula to keep it new and exciting:

  • Tease
  • Laugh
  • Challenge

Pick a flavor, turn it into a text and hit send. Mix up the flavor and intensity of your texts and  she’ll be hanging on every word. Bonus points for combinations.

After a couple rounds of puffing your feels-enhanced texts, she’s quite eager to keep the Tinder conversation going with you.

#5: Dating don’ts

The typical date goes horribly wrong. But after reading this tip, your dates will be a flying success.

Have you ever set a date and got this message?

So what are we going to do?

I can’t read your inbox, but my guess is you at least once answered this:


An actual photo of me storming in your room

Going for a bite is an awful idea for a first Tinder date.

Let me paint you a picture.

You want to make a good first impression, so you take her to an expensive bistro.

With a glistening forehead, you lead her inside and pick out the table where you’ll hopefully make her laugh for the rest of the evening.

You sit across each other. And as you stare into her eyes, you feel the tension in the air.


You fire off the questions you prepared yesterday and the conversation starts to roll.

While the conversations sometimes crawls down to a halt, it always fires up again. The date feels pleasant.

So after dinner and a nightcap, you take her home.

You’re confident she had a good time, but as you go in for the kiss, she gives you the cheek.

Frustrated you return home, pump a few globs of lotion into your hand and take out the fleshlight.

What happened?

I already gave the answer away, did you see it?

The date was pleasant.

A personal question for you.

If you go out with a woman and all she makes you feel is, “She’s nice.”

Not exciting, not thrilling. Just ‘nice’.

Would you go out with her again?

I hope not. (Although I get it if she’s a stone cold stunner).

But more importantly, if all you made her feel was ‘nice’, she is definitely not going to want to see you again.

Unless she’s super lonely, or you’re super ripped.

Holy Tip:

I wrote a guide about what to do after the date.

When to text her, and what to text her.

Read my guide with examples right here: What To Text Her After The Date.

Rather than going after friendless women, or jabbing steroids into your butt, you can also make the date exciting!


Read all about it in the next tip.

Hint: it’s not the movies.

#6: How to have a successful date (LIFE CHANGING ADVICE)

You’re about to get life changing advice on what a great date actually looks like.

Have you ever gone on a date, felt like it went great and then received this the next day:

Hi. Thanks for the night out. But I think we’re better off staying friends. Bye

It’s okay, bro. There’s plenty of (star)fish in the sea.

And with what you’re about to learn, you’re definitely going to reel in those bearded clams.

Let’s get started.

The foundation of any good date is adventure. And the predictable has no part in that.

The easiest way to add more kick to your dates, is to think of your rendezvous as a triathlon, rather than a marathon.

Prepare multiple events.

Play some laser tag, drink some mimosas and finish off the evening with ice cream cones and a walk round Chicago’s Bean.

I know I compared dates to sports, but don’t tire her out too much. Or else she won’t have enough energy for bedroom athletics.

So keep the venues within walking distance.

What’s more, by switching up the venues you walk off the nerves. And you get to know each other more naturally than being cooped up inside a tiny café.

And when the inevitable moment arrives to sit down and have a drink, sit NEXT to her, not across from her.

By sitting hip to hip, you both get a chance to unwind. The pressure of having to perform melts away.

The conversation stalls? No problem.

Because you’re not looking at each other for stimulation, there’s no stress.

Holy Tip:

Seeing as you’re both enjoying the same view, look around for the funny.

“You see that dude with the mutton chops and the mullet? That’s my dad. We don’t talk anymore.”

Plus, women who are into you really like it when you sit next to them. A buddy of mine recently said that when he was a teenager, he always sat across from girls on dates.

“I thought you HAVE to sit across each other. Because that’s what you see in every romantic Hollywood movie!”, he said. But as the date got more exciting, these girls always told my pal to come sit next to them.

“They were so demanding. And I didn’t understand, because I thought hip to hip was for losers. Was I being friendzoned right now?! But as soon as I sat next to them, they scooched up to me and got way more than friendly.”

“Turns out I was the loser!”

Learn from my innocent bro.

#7: Best Chicago date locations for Tinder

After you’re done with this tip, you’ll never wonder where to take your date again.

Going out for quarter pounders is a slap in the face. Buying her a trip to Paris is like going down on one knee.

What’s the happy middle that isn’t going to cost you an arm and a leg?

Honestly, any place that helps you show off your personality.

Are you dark and moody, go to an underground café.

Are you artistic and zesty, go to a jazz café.

If your personality is more bland than oatmeal, score points by taking her to a place with a stunning view. Or perhaps a bar with epic flaming and sparkling cocktails.

Here’s some other Tinder date ideas.

1. Pedaling your way to her heart

Chicago has a surprising amount of bike paths. Ranging from under 3 miles for the one-speed casuals, to over 20 miles for the lycra wearing road captains.

Keeping it to the shortest path, take a trip through Sculpture Park. It’s 40 minutes away from downtown Chicago.

With over 60+ artworks and plenty of greenery, it’s a super low stress way to get to know someone.

Don’t know what to say? Call out what you see.

“That artwork looks like a sad vagina.”

And if you want to tack on a few extra miles, continue through the Ladd Arboretum.

Holy Tip:

Bring a bottle of wine and some snacks inside your backpack.

And when the time is right to get cozy, hit the breaks, take out your blanket and roll it out onto the grass.

Next enjoy a romantic evening under the stars.

2. Montrose Beach

No summertime trip to Chicago is complete without visiting Montrose Beach.

Yes it’s touristy, crowded and filled with screaming children (in the afternoon).

But it also has volleyball nets, late night luaus, and live music. Plenty fun activities to do together!

Parking is also free.

Definitely visit Montrose in the summertime.

3. Shake your booty at the summer festivals

In Chicago it’s party month, every month. But especially during the summer, the city’s downtown and lakefront are brimming with the song of guitars, saxes and violins.

House, gospel, blues, jazz, classical. They got it all.

And if you want to give your ears and money-maker a break, grab a bite at the market food stalls.

Holy Tip:

Sometimes you come face to face with Tinder’s ultimate bad guy:


The conversation dies down and you don’t know what to say.

You shoot her a text anyway.

But she didn’t bite.

Suddenly it seems like she’s ghosting on you.

That’s rough, dude.

And I know. I was ignored all the time when I started out.

But now I have a library full of homemade answers ready to grab her attention.

And even when I can’t copy paste a line directly, I can use it as inspiration for something new.

My whole library is reserved for my courses, but you can get a collection of 10 Texts That Always Work, for free.

Get it now.

4. Sneak your way into a secret bar

When alcohol was illegal, speakeasies popped up all over Chicago to serve firewater to the thirsty locals and mobsters.

To hide from the heat, speakeasies were tucked away below restaurants and hotels, or took cover behind fake walls.

While bars are free to openly sell hooch, the speakeasies never disappeared.

So if you want to impress your date with your ties to the underground, visit one of these prohibition bars. You don’t need to know a secret handshake, just the directions.

Google ‘secret Chicago bars’ and plop down a pin on your map. Because just like in the old days, many speakeasies don’t use signposts.

An added bonus is that many of these pubs double as wine bars and jazz clubs.

5. Tiki Bar

Chicago has brutal winters. But a tropical paradise is never far away in the shape of a Tiki Bar.

So if you want to save yourself a back breaking international flight to French Polynesia, go down to Lost Lake and enter an island paradise. Order rum filled drinks garnished with tropical flowers, colourful bendy straws and fresh herbs.

Three Dots and a Dash is considered by many to be the best. But as with anything popular, it’s crowded. So if you do decide to go, avoid the weekend.

6. Turtle Racing at Big Joe’s

It’s pretty simple.

Go to 1818 W. Foster Ave. Enter Big Joe’s bar and watch reptiles race each other to the finish line.

But before you can watch the turtles launch out of their starting blocks, you might have to wait a bit. You see, there’s only so many races in an evening. Six to be exact.

And the only way you can place your bets is by ordering drinks. Every drink at Joe’s is worth so many tickets.

The more tickets you have, the bigger the chances a turtle will run across the field in your name. You read that right. Not everyone gets to sponsor a tortoise.

When racing time begins, Big Joe steps out from behind the bar with a big bucket filled with tickets. Joe then blindly reaches into the bucket,grabs a ticket and yells out the number on the paper.

Now is the time to look at your own stubs.

Do you see the number that Joe called out? Congratulations, a turtle is about to race in your honor.

If your leatherback finishes first, you win a T-shirt.

And when you’re done racing turtles, you can chuck darts at a board, shoot some pool or throw back a brewski at the bar.

One last thing.

As is fitting for such a chique establishment, Joe only accepts cash.

7. Stroke some pussy in a cat café

How about a date in the happiest place in the world. The Windy Kitten Café.

Sink down into a couch, order a cup of joe and pet a kitty cat. Or two.

So cuuuuuuuuuuuuuuuuute!”
—Your date

The best part?

If you fall in love with your feline friend, you can adopt him or her.

And there’s a bonus: women love guys with a sensitive side.

The only time I’d advise against taking her to a cat café is if you’re already known as the overly caring, I’ll-walk-to-the-end-of-the-earth for-you type. In that case it’s better to do something manly. Like rock climbing or go-karting.

Check out Brooklyn Boulders for scaling fake rocks. And K1 Speed for getting into a little motorized deathtrap.

You now have everything you need to set up dates with sexy singles through Tinder in Chicago. Better free up your calendar, because you’re going to be knee deep in dates.

Louis Farfields

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