How Can You Meet Singles in Chicago? 

Chicago is considered the second most alluring city in the world due to its attractive architecture, historic landmarks, and known universities. It tends to be the largest city in midway and offers a variety of places to meet singles.  

In fact, according to a survey, Chicago is the most preferred city for singles to date, and around 60% of its three million residents are single, so it’s no significant challenge to find things to do in Chicago and someone to explore this phenomenal city with.  

However, many single nowadays don’t like the concept of dating sites and wish to meet singles in an “old fashioned way.” So, here are the best ways to help you meet singles in Chicago.  

  1. Explore incredible places  

It’s a no-brainer that going to the fun places, including live music events, bars, and stand-up comedy shows, is a great way to meet new potential dates—most individuals like going out every weekend to enjoy their favorite artist.  

So, chances are you can find new people who share your sense of humor or music taste and offers ideal grounds to start a good conversation. The other option is to sign up for co-ed sports as Chicago has countless sports options, including beach volleyball, dodgeball, and kickball. Such activities allow you to find people who share similar interests with you.  

  1. Matchmaking Services  

The Chicago matchmaker known as Master Matchmakers has been bringing people together long before they were swiping right. Matchmaking as a profession is still alive and well. They often meet with new clients, interview potential matches, share dating advice, and attend networking events. However, one should always opt for the service that ensures background checks, administering personality tests, and building their clients’ psychological profiles.  

Remember, the key to building a successful, trusting, productive relationship with your matchmakers revolves around having realistic expectations about love.  

man and woman standing side by side during daytime
  1. Put the word out to your Married Friends 

Many individuals don’t prefer asking their friends to set them up with someone due to the reason of coming off as desperate. However, it’s a good idea to reach out to your married friends for help, as their spouse possibly knows some single friends they may be willing to set you up with.  

One piece of advice will be to ensure that you have a great understanding of their spouses and believe their judgments. Otherwise, you might end up in an awkward situation with that person.  

Following are the tips for a blind date: 

  • Always keep the expectation low as you are just going to meet a person.  
  • Even if you are just going for coffee, ensure to ask her, “where would you like to go on a coffee” as it makes women feel special.  
  • Ensure your clothes are nicely fitted, ironed & clean, and your facial hairs are well-trimmed.  
  • Do not ask personal questions on the first date; talk about the common interest to see whether you both laugh at the same joke and share the same values and goals.  
  • Some individuals are nervous on a first date, and you can’t know everything about a person at the first time, so don’t be quick to judge.  
  1. Learn How to Talk to Strangers   

You might have one of those experiences where you have seen someone pretty and exciting. However, you have never tried to approach them. There are numerous ways to approach people- simply go and ask them a neutral question like asking them about the best places to have a lunch or dinner or a café to get some work done on the laptop or simply asking about the time since your phone’s battery is dead.  

It’s all about getting that fear out of your head of approaching strangers. All you require is to do some practice and get comfortable with it.  

  1. New Intellectual Hobby-Learning a new Language 

What are your thoughts about learning a new language? Attend new language courses and discover numerous language partners. Chicago has the best universities where you will see international students and professionals who wish to readjust their English with you, and in return, you can learn their mother tongue.  

If you don’t want to learn a language, opt for painting or other art-related activities. The idea is to pick a hobby where other people are involved too. This is where you meet like-minded individuals.  

Also, you can opt for volunteering at a local non-profit or an event like the Chicago Marathon. This is because volunteering offers you various opportunities to meet like-minded individuals.  

man in gray zip up jacket standing beside woman in black and white floral dress


Dating in a city like Chicago is not a challenging task since many singles are looking for the same. Dating is all about finding the right person, and it can be adventurous and fun and exciting at the same time. However, if you have realized that your life includes the same routine and same people- it’s time to get up from your comfort zone and find new hobbies. Who knows, you might end up finding the right person in the process.  

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