Complete guide on dating in Chicago

Dating tips
November 18, 2019

Chicago is one of the biggest American cities with a population of more than 2.7 million locals and 58 million tourists from the United States and all over the world. It’s known for its rich culture, highly developed business and technology life, and buzzing social life.

Chicago dating scene is open compared to most American big cities. People are busy and ambitious, but not too much — they take time to have fun and invest in personal lives. Still, you need to get to know the city to get laid — and my guide will help you to get through.

Girls for sex in Chicago

I love that girls here are fun and down-to-earth. All whom I dated weren’t bothered about what other people thought of them, and just went along with any dating activity. A nice bonus — a lot of girls love sports and can talk about their favorite teams for hours.

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Getting a date in Chicago

Chicago dates are outgoing and open to new experiences. You don’t have to offer some luxury activity to your date just to get noticed. As soon as you are fun and interesting to talk to, you have high chances for success. Also, girls here are direct, so you need to be upfront with your intentions and offers. Don’t hesitate to come directly to the girl you like and asking her out.

Daytime dating tips

Chicago is not the busiest nightlife city — you stand the best chance of picking up a girl during weekends after lunchtime. Casual settings are your best friends — you can get a date in the park, cafe, or a coffee shop.

You need to be decisive in your flirting attempts. Otherwise, the date might prefer social media or online browsing instead, completely ignoring your attention signs. Don’t expect women to pick up your implications; instead, tell them directly.

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Top areas for meeting girls

The best city areas for daytime pickups are on Michigan Avenue. This street is full of attractive single girls or women who like this spot for daily walks and meetings with friends. If you are looking for an ambitious and successful partner, your target area to getting laid in Chicago is the Loop business area. In this district, you can meet a smart and beautiful woman in coffee shops or restaurants near the office buildings.

My favorite spots are Fashion Outlets, Harlem Irving Plaza, and Woodfield Mall. You can explore other malls in smaller areas and check out shopping districts.

Nighttime advice

Although Chicago is not known to be the busiest night city, it still has some amazing clubs where you can find a potential hookup or a long-term relationship partner. The rules of the game are simple: you need to dress nicely, prepare pickup lines, and buy drinks. I’ll walk you through my top picks of nightclubs.

Best nightclubs to meet girls

Chicago is not the nightclub kind of city, so not all clubs are good. You need to select your options thoroughly. Otherwise, you might get a pretty boring place with sloppy security and poor drink choices. To help you avoid such traps, I share my personal night favorites.

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Magnificent Mile

One of the most popular nightclub streets in the city. Clubs here are known for their elite audience and extravagant atmosphere. These are not cheap options — you have to be ready to pay at least $20-30 for drinks.

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Lincoln Park

If you want to get the attention of European tourists, Chicago’s Tzar bar is your go-to destination. Here, you’ll see a lot of international visitors that all speak fine English. Also, the club is located in a nice area with intimate spots where you can continue your date. The club, however, has quite a strict face control, so you need to take good care of your appearance to get in. If you have trouble with that, your next best shot is at Crescendo — another bar at Linkoln park with fewer requirements.

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Bull and Bear

A small bar with breathtakingly attractive women. It’s not as mainstream, and only very selective girls come here. They are usually experienced in the dating game and are openly looking for a hookup. Their confidence makes things much easier — you only have to start the conversation, and they’ll help you to carry on. The bar complements this first impression by providing a cozy atmosphere and relatively cheap drinks. On top of that, it’s not that crowded at night.

Cougar dating and meeting mature women

Chicago’s cougar community is perhaps in my top five of favorite ones. Women here are active and easy-going and straightforward about what they want. On top of that, they aren’t spoiled with too much attention, so it’s easy to impress them. You don’t have to save up for a fancy date or worry too much about appearance — lively personality is the key success factor in the local milf community.

Getting into Chicago cougar dating gets even easier if you know where to look. Here’s my list of favorite spots with the best milfs’ experiences.

  • Chicago hooks up bars — Wild Hare, a bar with a relaxing atmosphere located near busy districts. Here, mature women usually come from work to look for a potential company or relax after a workday. They don’t mind if you keep them company, only be sure do ask if they don’t mind a date. Some of them might be married and not seek any additional pleasure.
  • Dance clubs — this is my favorite type of occasion to meet mature ladies. You can sign up for dance classes and join a group of attractive older women who are willing to experiment, express themselves, and wouldn’t mind a date. Also, it’s a great chance to level up your dance skill — something that always comes handy on dates.
  • Park date. Grant Park, Millenium Park, and Lincoln Park are great spots for meeting milfs and taking them on dating right away.
  • Social sports activities: in a tennis group, you can meet classy Chicago ladies who work on their fit shape and look for new experiences. It will work especially well if you are good at tennis – then it’s a free opportunity to impress your date.

Participating in social activities and club gatherings is the shortest and most natural way to find cougar dates. For older ladies, it’s important to have common conversation topics with their date, so you should use these meetings as an opportunity to speak up about your interests and opinions.

Best dating insights for Chicago tourists

If you want to get the most out of your time in the city, I recommend using online dating services beforehand. My favorite one for Chicago dating is Pure. I tried several others, like Tinder or AdultFriendFinder, but they didn’t impress me with the same selection of available dates. On Pure, girls were ready to meet me anytime, and they were serious about hookups.

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Top Chicago dating tips

My favorite dating spots in Chicago are mostly restaurants and bars. For one thing, I like the local selection of food and drinks, and I also appreciate active sports communities. Whenever I am in the city, I try to go to at least one sports bar. Girls here are very passionate about baseball and basketball, and it’s a real pleasure to discuss one of my interests with someone who truly cares.

My favorite spots are Geia’s Cafe, Bavette Bar, Cherry Circle Room, Sappori Trattoria — I enjoy the atmosphere of these places and the fact that they aren’t too crowded with tourists. When I am looking for a date in Chicago, I want to meet someone local.

Also, my list of tips wouldn’t be full without a mention of comedy clubs. Chicago stand-up events are, in my opinion, one of America’s absolute bests. Whenever you are in the area, find a minute to go to Laugh Factory or The Comedy Bar. The lighthearted atmosphere and great okes create favorable conditions for successful dating. If you are good at stand-up comedy, you can even ask about participation — but that’s only if you have the experience. Otherwise, it’ll be the worst date ever.

Chicago online dating tricks

I learned a while ago that online dating is a lot different depending on what kind of city you are in. In Chicago dating, I often find myself immersed in a casual dating community. These shouldn’t be necessarily sex dating sites, but services for casual encounters, where sex may or may not be included.

You have to understand that although Chicago girls are casual about sex, they also appreciate other aspects of date, and you’ll have to impress her with your personality first.

Casual dating apps

My top choice is Pure — it’s a nice anonymous dating app with a big Chicago community. It’s casual and doesn’t put any obligations on the user — you don’t even have to tell your real name, only location and email address for verification — but then again, it’s not public. Another top choice of dating website is Adultxxxdate, a sex dating community with a huge user pool.

To get a local date, make sure to get out of tourist districts when you want to find sex in Chicago. Others, you’ll see profiles of people nearby who are most likely to be tourists. To meet girls in Chicago, visit residential areas, and look for matches from there. If the app allows targeting a particular zone of the city, you should try that out — it’s easier than commuting all over the city.

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Pure, platform with no bots and fakes

In Pure, the algorithm will delete your account an hour after you start searching for a partner. If you match, you have another hour to talk in the chat — then it will also be automatically deleted. This makes the service inaccessible and uninteresting for bots, fakes, and crooks. Pure users are alive personalities who do not hide their desires and want to find a partner in the next hour.

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Using live cam chats

Another lifehack is that Chicago has one of the best cam communities. I’ve read this online for a while, but wherever I am in the city, I like to find a cam girl and then schedule a live meeting, if service’s rules do not prohibit that.

The easiest solution is to visit service with web chat features, meet a girl you like, and contact her directly. This way, you can easily get a free date with a camgirl on the very same night.

My favorite bars for getting quick hookups

Chicago has legendary hookup places all over the city, but they are well-hidden from tourist’s eyes. Usually, you need to look well at residential areas and google less promoted locations — this is where your chances for high-quality hookups are the best. It’s a lot of work, but I can make it easier for you. I’ve been in Chicago dozens of times and never had to spend my stay alone, all thanks to these seven favorite locations.

14 West Elm Street

This dive bar for singles and swingers is a city’s must-visit. It’s located in a great busy neighborhood, and the place gets full at night. Most importantly, it’s mostly visited by local people — you won’t see many tourists around.

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The bar has great drinks at affordable prices, and DJs deliver great vibes. It almost feels like a premium experience for what certainly isn’t a premium cost.

El Hefe

This is a weird location to meet dates, although it always worked out well for me, for some reason. Imagine a place with confetti cannons and a big bar. Only it’s a sports bar with screaming fans and an amazing sports spirit.

El Hefe Chicago - Complete guide on dating in Chicago

Such a mood makes the place a must-see to all sports fans, but even for those who are not into games, the spot has a lot to offer. Whenever I go to Chicago on weekends, I always am a night or to visit El Hefe. Trust me, it worth it.

Slippery Slope

This is one of the best dance bars in the city. Great crowd, skiball games, and fun activities make the experience wholesome. Add to this the free choice of music and sick cocktails — and you get close to a perfect night out.

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This is not the best place to get laid in Chicago, but it’s perfect for bringing a date. I usually don’t look for hookups here — it gets too crazy for that, but it’s an amazing opportunity for those who already met people online or have a partner.


If you don’t have anyone to spend the night with, head straight to Federales. It’s a vibey taco place, incredibly popular among millennials. If you want to get a 20-30-year-old date for a one-time fun, it’s a nice spot to spend your weekend or workday night.

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This bar isn’t as much about crazy dancing or games, but encourages people to talk — you will have a lot to talk about with your potential date. If you are only getting to know the person, it’s a perfect place to bond before actually hooking up.

Bunny Slope

This bar has hot tubs, open to people during parties. You don’t see something like that every day, and it’s freaking worth it. The bar hosts regular open events where people can meet hookups or bring dates.

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It’s a nice place for a group of friends – you can have the best fun of your lives and make a fair share of embarrassing pictures. Also, to my mind, their cocktail selection is legendary.

East Room

If you are into hipster’s gatherings, you’ll feel right at home in East Room. I am not much of a hippie myself, so I am not a regular visitor, but from what I’ve seen from a couple of times in the bar, it’s a must-visit spot of a hookup in Chicago for those who are into this culture.

East Room Chicago - Complete guide on dating in Chicago

The bar has a nice DJ venue, mind-blowing dance floor, and awesome tracks. Even if you don’t get laid, you will have loads of fun.


As a person who visited actual Berlin pubs and bars, I can confirm that Chicago’s version comes pretty close to the original experience. The same amount of crazy drinking, nice beer (although not quite as good as the German one), and open-minded crowd leave nice chances of getting laid during the night.

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Here, people can do pretty much anything they want and don’t get judged. If you want a date with no continuation, this is an amazing place to start with.

An ideal Chicago man

To be a successful guy in Chicago’s dating game, you don’t need a lot of money — that’s already good news. All you need to do to maximize your chances s to be decisive — girls here like guys who know exactly where they want to take the date and how it will go.

A healthy mix of spontaneity and planning will serve you well. Make sure that you are open to new possibilities and girl’s suggestions, but you shouldn’t be a clean slate when going on a date. It’s better to have a rundown of top spots in mind — this way, you won’t feel awkward.

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Gaming dangers

I wouldn’t say that dating in Chicago is a dangerous deal, but there are won problems involved. My most common issues were with drunk guys — face control in clubs gets sloppy, and bar security also doesn’t always do a good job at monitoring their guests’ behaviors. As a result, I was approached by guys who wanted to hit on my date, and it ended in a brawl a couple of times.

Luckily, my experiences didn’t put me through getting arrested, but it very well could’ve ended worse. So, avoid drunk guys and go to reputable places with solid security.

Maximizing your chances of getting laid

To get a date as fast as possible, you shouldn’t close yourself on in a single type of dating style. Be open to new adventures and join various sexual communities, from Craigslist to BDSM. Ultimately, it will make you much more experienced and give you a richer personal life.

You have nothing to lose and a world of new opportunities to gain. Here are some communities that I think everyone should join when visiting Chicago.

Gold Diggers and Sugar Babies

I wouldn’t say that sugar baby dating is popular in Chicago, but it’s a rising community. Its non-mainstream nature is what makes exploring sugar dating in Chicago so tempting. If you are a mature guy, you should consider getting yourself a younger date. It’s a great confidence boost, plus, it’s much cheaper to do in Chicago than in other big American cities.

Swinger Clubs and Naturism

Chicago swinging lifestyle is also not as popular as, say, in LA, but that’s exactly what has drawn me to the community. Couples here are very welcoming about letting other singles join them for a threesome. You might find yourself in a position where you can choose between couples.

To maximize your chances of a fast swing, I suggest joining online swinging services, where hot girls in Chicago can meet you in less than an hour. Here, you can describe your experiences and expectations and let other people join you for a great sexual adventure.

Expenses for Chicago dating

An average daily budget for a Chicago trip can range anywhere from 50 to 1000 dollars. It’s possible to get by with less than half a hundred bucks, if you choose free dating places — like parks or open parties, and save up on accommodation.

If you are on a tight budget, I would advise you save most of your cash for the date itself. Even if you are broke, you should at least give the impression of a decent guy — so make sure to save at least 30 dollars for a date. It’s not a must, but it will make your dating attempts much more productive.

Cheap food can be bought in a grocery shop for less than $3 — you can even make a simple meal. For restaurants, expect to pay at least $8 for a meal — we aren’t talking premium options, of course.

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Where to live in Chicago

Accommodation in Chicago isn’t too expensive. On the one hand, it’s not a highly touristic city, but there is enough competition on the market, so hotels are forced to lower the price bar. You can find a place to stay for $10-11 per night, and it would look decent.

However, if you are planning on bringing your date to the place, look at 4-star hotels that cost approximately $60 per night.

Transportation in Chicago

You can use custom bus services that would drive to any location of the city. These shuttles are more expensive than public transportation, but also faster and more convenient. My favorite provider is — the bus can transport you to Chicago from almost any American city for a reasonable price. It also works in the town.

If you are traveling by car, you need to explore the traffic situation in your expressway. The most common routes include the following areas: Chicago Skyway, The Stevenson Expressway, Dan Ryan in downtown, etc. Each expressway has a particular traffic situation — if yours is a busy one, don’t risk it and take a longer road by crossing quiet residential areas.

How to work in Chicago?

You can find freelance work or get a temporary position on local job boards. Start the search beforehand — the process can take up to 1-2 months.

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Mobile connection and Internet

If you are staying in the city for a while, I suggest signing a deal with one of Chicago’s leading connection providers. The most popular internet companies are AT&T, RCN, Xfinity, WOW!, Spectrum, etc.

If you are here for a couple of days, free hotspots should serve you well enough. In Chicago, free Internet is available in airports, Millennium Park, museums, Chicago Public Libraries, and the Cultural Center. Also, your hotel is likely to have a WiFi router, ask them for a password.

Chicago gambling advice

By its gambling opportunities, Chicago isn’t exactly Las Vegas — you won’t find premium spots and active gambling communities. Still, it offers enough attracts for tourists — you will hardly have time to visit all the best ones anyway. My top picks are Big Top 2, WinStar Casino Boat, Rivers Casino, and May’s Lounge. These spots provide a nice combination of premium experience and more or less affordable prices.

Drugs policies

Marijuana is considered illegal in Illinois, which means, it’s also illegal in Chicago. However, medical marijuana is allowed if you have a medical card and an authorization. Weed can only be purchased from licensed providers. Even so, medical weed shouldn’t be used in public — only home use is allowed.

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Sports and gyms

Looking fit in Chicago is a top dating advantage — don’t forget that local girls are pretty interested in sports. It’s better to match this high expectation and get in shape while you are in the city. My favorite gym centers are Urban Athlete, Anytime Fitness, Lakeview Athletic Club, and Buck down Athletic Club.

Additional health- and hygiene-related activities include SPA and hair salons. You can consider getting your date a gift from one or even scheduling a meeting here. My top pick is Allyu Spa — I like prices and the service quality.

STDs and HIV

Statistics on HIV diffusion in 2017 show that there are more than 19,000 people with HIV in Chicago, not including tourists. From 2,7 million population, it’s a rather small percentage — still, you should be careful about protecting yourself. Additional common sexually transmitted diseases are syphilis, gonorrhea, and chlamydia.

Safety guidelines

Although Chicago’s crime rates have declined since the 1970s, the city still has dangerous areas, and some of them are located near tourist districts. An inexperienced tourist is easy prey for scammers and criminals — be careful about accepting any offers or going to suspicious bars. Instead, stick to well-lit streets and follow tourist guidelines. Don’t rely on Google Maps too much — GPS can lead you through some shady streets.

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Where can I get laid in Chicago?

People go to bars, restaurants, and nightclubs. I’ve listed my favorite places for nighttime and daytime dating in this guide — scroll up to see the list.

Where can I find girls in Chicago?

You can go to parks, coffee shops, bars, and clubs. If you want to start a long-term relationship, I suggest exploring lesser-known areas, where people aren’t necessarily looking for a hookup. Business districts are great places to find an ambitious woman.

How do you meet people in Chicago?

You can do your research on online dating sites and apps beforehand. I recommend checking out Pure and Adultxxxdate. After you’ve matched up, you can schedule a live date in the city.

Where do singles meet in Chicago?

Best sex places in Chicago are public places like bars and restaurants as well as during social gatherings — sports fan clubs, interest clubs, events, business meetings. Depending on what kind of people you want to meet, you can find an event with any audience.

It’s time to see you off

Chicago people are classy but easy-going. In my experience, they don’t care about money as much as in New York or LA — so your budget is not necessarily a dealbreaker. Girls here love to eat and exercise — your date won’t mind having a pizza or even getting some junk food.

People here know how to have fun, but they are also focused on long-term perspectives, which works well for any kind of dating. It’s a place of opportunities, not just in terms of career but in sex life as well.

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