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Chicago Singles: Best Dating Tips to Find a Partner off- and online

Chicago, on the shores of Lake Illinois, is well known for its beautiful architecture, historic landmarks, and world-class university. One of the largest cities in the Midwest, there are plenty of places to bump into singles in Chicago – drinks at a speakeasy, kayaking on the lake, exploring the city’s various museums and art galleries, or watching one of its many sports teams.

According to a 2019 WalletHub survey, Chicago is the sixth best city in America for dating. And with upwards of 60% of its three million residents being single, you’ll have no trouble finding someone to explore this beautiful city with.

Why dating offline is hard in Chicago

Although Chicago is rated as a great place for singles (WalletHub’s survey gives it sixty-four points out of a hundred), many factors make finding someone offline challenging, chiefly the weather. Midwestern winters mean most people prefer staying at home, where there’s heat, snacks, and Netflix.

Not to mention, there’s the city/suburb divide (Someone from Lakeview dating someone from Wicker Park? Not happening – who wants a long-distance relationship in the same city?) and sports affiliations (Capulet and Montague ain’t got nothing on the Cubs vs Sox rivalry) to make things difficult.

Plus, with the ever-increasing pace of modern life, it’s often difficult to carve out the time to date, between work commitments, hobbies, and making time for family and friends. In addition to this, hookup culture and finding someone who shares your values and who seems worth dating long-term is a big challenge when dating traditionally.

Best places to meet singles in Chicago

Nevertheless, many singles still prefer to look for dates the old-fashioned, offline way, or at singles events. Here are some more recommendations:

  • You could try and hit one of the many excellent bars or pubs – buying a good-looking stranger a drink is a time-tested strategy for getting that first date.
  • If the prospect of dark noisy rooms doesn’t appeal, sign up to volunteer at a non-profit or charity – you’ll make a difference in the world and get to know like-minded singles in Chicago at once.
  • Don’t be afraid to let your geek flag fly – you might just find the love of your life at a fan convention, trivia night, or music festival.
  • If you’re a student (traditional or otherwise) study buddies can sometimes become more than friends, if you’re lucky.

Why you should go online and use eharmony

As mentioned previously, offline dating is difficult in Chicago, for many reasons – the weather, the traffic, the possibility of a great first date turning out to be a Cubs or a Hawks fan.

With eharmony, members are matched according to their likes and their vision for a relationship. There’s a Compatibility Quiz for long lasting relationships, making your odds of finding The One higher right from the get-go. In addition, eharmony’s big and diverse member group means finding someone who shares your values is that much easier. Plus, profile details are stored for easier recall later.

eharmony also allows you to start conversations with potential matches so you can see whether there’s a spark right away. And the easy registration process means you can get started hunting for your happily ever after in no time, and with very little effort.

And who knows? You might even be tempted to cross the city/suburb divide, like Cynthia (from Schaumberg) and Erik (from Chicago) did. She’d nearly given up before her friends convinced her to make the hour drive. A good thing she did, because if she hadn’t, she would never have met Erik, in September 2005. Keeping a relationship going with that kind of commute was hard, but they persisted, and in September of 2007, Erik proposed, at their favorite French restaurant.

Or you could be like Kerry and James, who – despite having grown up within a mile of each other, having both gone to Indiana University, and having many mutual friends – only met on the site. They got married in October 2008, moved to Chicago, and adopted a puppy!

And that’s just two of thousands of happy endings that started with eharmony. But once you’ve made that online connection, where do you go on an actual date?

Top 3 first date ideas in Chicago

Chicago has something for everyone, whether you’re the casual cocktail type, the kind who goes kayaking on weekends, a classic dinner and a movie kinda gal, or something completely different.

  • Bookworms and gourmands alike will enjoy The Book Cellar on Lincoln Square, a cozy independent bookstore with a café where you can grab a bite to eat in between browsing, or while away an afternoon with a book and a hot beverage.
  • The bar scene more your kind of thing? When in Chicago, do as the Chicagoans used to do during Prohibition and head to a speakeasy. If you want one that’s easy to access, head to Violet Hour, or try Milk Room or Room 13 for something a little more exclusive.
  • There’s always something happening at the Chicago Cultural Centre, or you can find inspiration walking around the city’s many architectural marvels, such as The Bean, the Baha’i House of Worship, or the Chicago Art Institute.

Find singles in Chicago city and enjoy the great dating scene

Dating, even in a city as single-friendly as Chicago, can be tough to navigate – there are so many people, but finding The One is still a bit of a task. After all, you don’t just want your date to be fun speakeasy company, or willing to go look at the exhibits at the Art Institute, you want them to be the kind of person you see yourself with long-term.

Dating – once you’ve found the right person – can be fun, romantic, adventurous and exciting. Just remember to be yourself – there’s nothing more Midwesterners value than authenticity. And with dating site eharmony, finding your perfect Chicago match is easier than ever.