Where to Meet Rich Men in Chicago, IL? (Except for Bars)

If you actually want to meet rich men in Chicago, you must be proactive and put yourself out there.

This means using popular dating apps and exploring different social settings and activities.

Where to Meet Rich Men in Chicago, IL?

1. Dating Apps

Successful men in Chicago use dating apps and sites because they have busy schedules with their careers and other commitments, which makes it difficult to find time to go out and meet new people.

Also, dating apps provide a larger pool of potential partners than they may encounter in their daily lives.

This is why Chicago dating apps offer a convenient and low-pressure way to connect with successful men.

Just make sure you don’t start the conversation with a generic intro.

Instead, break the ice with something like: “How much does a polar bear weigh? Enough to break the ice and introduce myself! Hi, I’m Cathy! “

Some popular dating apps include:

2. Business Conferences

Business conferences are excellent places to meet successful men in Chicago because participants are there to network and meet potential business partners.

People at conferences expect to connect with new people, which makes it the perfect place for you to meet an ambitious man.

The best time to attend these conferences is during lunch breaks, happy hours, or networking events, as these are the times when people are more open to meeting new people.

To approach a successful man at a business conference, use a funny icebreaker to make him chuckle and ease the tension.

You can say, for example, “Excuse me, I couldn’t help but notice that you seem to be the only one here who understands this presentation. Would you mind explaining it to me in terms that a fifth-grader could understand?”

Some popular places to find business conferences in Chicago include:

3. Investing Seminars

Chicago investing seminars are a great place to meet rich men who are interested in building their wealth and financial knowledge. 

Rich men in Chicago attend investing seminars to network with other like-minded individuals and learn about new investment opportunities. 

The best time to attend investing seminars is before the start or during the breaks, as this is when attendees are most approachable. 

A great way to approach a rich guy at an investing seminar is with a funny joke to break the ice.

For example, you could say something like, “I’m here to learn how to invest, but let’s be honest, I’m better at investing in shoes than stocks.” 

After the laugh, you can follow up with a more genuine conversation about the seminar or investment strategies.

Some popular places to find investing seminars in Chicago include:

4. Co-working Spaces

Chicago co-working spaces are a great place to meet rich guys because they attract entrepreneurs, business owners, and freelancers who are focused on achieving their goals. 

Successful men in Chicago go to co-working spaces because they offer a professional and collaborative environment that allows them to network and meet new people. 

The best time to go to co-working spaces if you want to meet rich guys is during networking events or lunch breaks when people are more relaxed and open to conversation.

The easiest way to approach a man in a co-working space is to ask for technical help with something.

For example, you could say: “I’ll be honest, my social skills are about as good as my printer’s. Can you help me to setup up a Zoom meeting?”

Some popular co-working spaces in Chicago include:

Related: Where to Meet Women in Chicago, IL?

5. Boat Shows

Chicago boat shows are a great place to meet wealthy men because they attract successful businessmen who are interested in boating and yachting. 

Wealthy men in Chicago often attend boat shows to stay updated on the latest trends in boating and to network with other enthusiasts. 

The best time to go to boating shows is during the opening hours when people are just arriving and are more likely to be in a socializing mood.

An easy way to approach a wealthy man at a boat show is to break the ice with a small joke.

For example, “I’m a pro at sinking canoes, but I figured I’d give boats a try. Any tips?” and see where the conversation goes from there. 

Some popular boat shows in Chicago include:

6. Golf Courses

Chicago golf courses are some of the best places to meet successful guys. 

Golf has always been associated with business and networking, and many successful guys in Chicago use golf courses to unwind while making valuable connections. 

If you want to meet rich guys at a golf course, the best time is during the week, particularly in the mornings or early afternoons. 

Weekends tend to be busier and crowded with regulars, making it harder to meet new people. 

An easy way to approach a man at a golf course is to use a simple funny icebreaker.

For example, “Excuse me, do you have any tips for hitting the ball straight? I’m pretty sure I’m just here to chase after my ball all day and give everyone a good laugh.”

Some popular golf courses in Chicago include:

7. High-end Gyms

Chicago high-end gyms are the perfect spots to meet successful men because they attract people who are health-conscious and have an appreciation for luxury amenities. 

Rich men in Chicago go to high-end gyms to maintain their physiques and socialize with other successful men and women. 

The best time to go there is typically during the early morning or late afternoon, which are the busiest times when successful men are most likely to be working out. 

An easy way to approach a rich guy at a high-end gym could be to ask him to spot you or to ask for his help on using a certain machine.

Some popular high-end gyms in Chicago include:


Where do rich men live in Chicago?

Some popular Chicago neighborhoods where wealthy men live include Medina, Laurelhurst, Madison Park, Broadmoor, and Queen Anne. But the easiest way to meet them is to use popular dating apps and explore different social settings and activities like boat shows and investing seminars.

How to attract a rich man in Chicago?

The best way to attract a rich man in Chicago is to use popular dating apps and explore different social settings and activities like boat shows and investing seminars. Also, smile a lot and be the first to initiate the conversation.

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