What Is Dating In Chicago Like? Dating In Chicago As A Woman, Man; Dating In Chicago In Your 20’s, 30’s, 40’s;

If you ask around, everyone will have their opinion about dating in Chicago. View points will vary based on gender, age, orientation, intentions, lifestyles, past relationships, experience, neighborhoods, race, looks, education, job, wealth, hobbies and family planning.

The truth is, dating is very complicated. There are so many factors that go into dating that it’s impossible to capture every perspective, justify every experience, explain every scenario and provide specific advice on how to do better. This is especially true if you are getting bite size advice from influencers on Tik-tok, Instagram or those who don’t have insight into your situation.

Related readDating In Silicon Valley  |  Seattle  |  Austin   Los Angeles  |  New York  |  San Francisco

Chicago Skyline Architecture

Dating In Chicago: Location, Location, Location

If you read other dating blogs or articles, the two factors people will reference again and again are location and weather. These two things are crucial but they are not everything. Neighborhoods matter because Chicago is spread out, more so than cities like San Francisco and NYC. Because of that, getting to and from places can be brutal, especially in the winter.

Given population size, people in Chicago typically have options, and they will weight their options closely. The difference between dating someone on the same rail line or not can make or break relationship possibilities. This is particularly true for about 1/3 of the year during winter. 

Neighborhoods also signal things about your lifestyle, socioeconomic status, where you might tend to hang out and where you might be willing to explore. Obviously there are exceptions to the rules but when people have options like in cities as Chicago or on dating apps, you will save lots of precious time by removing doubt and by making yourself more marketable.

Men in Chicago typically will travel further than women for dating and relationships but that does not mean a woman will tolerate distance. Typically, a 2-3 mile radius is what most women will set in their profiles in Chicago, but typically, people are more flexible when meeting people in person. The reason for that is because you have to have some filters in place to sort/prioritize folks on dating apps, otherwise it can be hard to sift through.


Weather & Dating In Chicago – Chicago Dating Culture

Weather is usually a factor when it comes to dating patterns and cycles but none more than Chicago. If you have ever spent any time in Chicago, you will know winters are brutal. It’s not unusual for people to stay indoors from December through March with the occasional visit to neighborhood gyms, bars, stores and cafes. Expecting someone to walk a few blocks from their home, office or train stop is a big ask and usually a deal-breaker when dating.

It’s not uncommon to see spikes in break-ups when the weather gets warmer (May-June) and people stay put during the winter. Of course, there are plenty of exceptions but knowing dating cycles in Chicago can help you be more aware and efficient. People base their entire lives around dating – where they live, work and who their friends are.

Related read: Date Ideas Chicago 

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Midwest Dating Culture, Trends – Chicago Dating Scene

Dating in Chicago or the Midwest for that matter is a rather unique experience. People in the Midwest treat Chicago as the big city – their New York. Lots of transplants here from those that like big cities but do not want to be on the coasts for whatever reason. As such, you can expect most people in Chicago to be either be recent transplants from other areas, move away after a few winters here or are locals who will stay in Chicago long-term.

If you are dating in your 20’s this may not matter to you but it should. People in the Midwest tend to get married younger and reproduce like bunnies more so than those on the coasts. Traditional dating norms like men making the first move is more common here than in cities like NYC, SF or LA. Similarly, people are more social than in tech cities which can be a breath of fresh air as you are more likely to meet people offline, organically than other cities.

These general trends lend to the notion that men experience a Peter Pan syndrome given the younger demographics of the city (more affordable than LA, SF & NYC) but also density and openness to offline approaches. If you are a tech geek, WFH or have a hard time being social, dating in Chicago may be extremely challenging for you.


Dating In Chicago In Your 20’s, 30’s, 40’s

Chicago is one of the few cities that I regret not living in, even if it was for a few months. It’s an amazing city with plenty to do and a youthful demographic that lends well to exploration, meeting new people and having a captive audience that doesn’t rely on tech as much as places like Seattle or San Francisco.

Given the amount of 20-somethings in Chicago, women in Chicago can definitely have a harder time dating as they get older, especially if they don’t get out much 1/3 of the year during the winter. With that said, women may find it easier to date in Chicago than in more introverted cities like Seattle or San Francisco.


Dating in Chicago, Dating Culture In Chicago, Dating Scene In Chicago

There are pros and cons of dating in Chicago. Depending on your unique situation, it can be easier or harder. Similarly, moving to a new city may allow yourself to open up, be more outgoing and meet new people than if you were set in your ways. 

In my coaching sessions, I review people’s backgrounds, interests, lifestyles, experiences, intentions and demographics to figure out where they can improve their marketability, screen people more effectively, cut off time wasters sooner and identify the qualities they seek in a partner. I love Chicago (museums, architecture, food, arts) and I try to make it out there whenever I can (as a visitor and also to visit clients).


Online Dating In Chicago, Best Dating Apps In Chicago, Chicago Dating Sites

Most people will stick to Bumble, Hinge, Match, Okcupid or Coffee Meets Bagel depending on their demographics. With that said, if you haven’t had luck on any dating apps, you might want to take a break and evaluate your efforts, deal-breakers, photos, profiles, first impressions, messaging and more.

For tips on how to do better on dating apps, read this.

For those that need help, I offer coaching services that span apps, offline efforts, image consulting and more.


It’s Just Lunch Chicago Reviews, Tawkify Chicago – Chicago Dating Services

Read this.


Online Dating Photographer Chicago

Contact me for updates on my next visit to Chicago for dating profile photoshoots.


How To Meet People In Chicago, Singles Bars Over 40 Chicago, Singles Events Over 40 Chicago

Stay tuned. Check out my Chicago date ideas for places to explore and check out.

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About Eddie Hernandez

Eddie is a dating coach for men & women in San Francisco (clients in NYC, LA, Chicago, & beyond ), as seen in the NYT & Bumble). He helps w/ profiles, photos, wardrobe, messaging, date ideas, red flags, lifestyle choices, hobbies, grooming/hygiene, communication, social skills & offline efforts.