10 easy, fun ways to make new friends in Chicago

As a former digital nomad and a remote freelancer/entrepreneur, I know how daunting it can be to make friends in a new city. You probably have questions like… How do I meet new people? How …

Ian Chew, MHFA

Written by: Ian Chew, MHFA

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Ian Chew, MHFA
Ian Chew, MHFA
Published on
Last updated on

As a former digital nomad and a remote freelancer/entrepreneur, I know how daunting it can be to make friends in a new city. You probably have questions like…

  • How do I meet new people?
  • How do I start a conversation?
  • And how do I deepen the relationship?

The good news is, all of these questions can be answered if you know where to meet like-minded folks. Why? 

Being in the right place is half the battle, as you can increase the odds of other people wanting to get to know you before you even talk with them. 

Over the last two decades, I’ve stayed on three continents — North America, Asia, and Europe — plus multiple cities. Each move required me to build new relationships or rebuild existing ones. 

Before I share a few spots where you can connect with interesting people, here are some shortcuts to help you make friends faster:

1. Befriend people that you meet on a regular basis 

This can be a work colleague, a fellow coworking space member, a neighbor, or even the cafe barista that fuels your morning coffee addiction every day 🙂 

There are two reasons why you should seriously consider this:

  • Save time: Carving out time in your schedule to make new friends takes extra effort. Talking to your colleague over lunch is a lot easier.
     
  • Leverage the mere exposure effect: The more familiar you seem to others, the more likely they will be open to chatting.   

2. Ask for intros


Whenever I move to a new city, I like asking my friends or collaborators if they could introduce me to folks they know well.

This helps me skip the whole do-I-trust-this-person dance — or, the small-talk-because-we-are-polite dance — and jump into meaningful conversations.

To make it easy for your friends or contacts to introduce you, here’s what you could say (modify based on your tone of voice, personality, etc.):

“I’m looking to meet new people in <city name>. Do you happen to know any good friends there?”

If they say yes, you could say something like:

>”Great! I’d love an intro. Here’s a bit more about me <what you do, an interesting/fun fact about you> and my email/phone number…”

3. Organize dinner parties 

Upon first impression, organizing dinner parties can feel like a lot of work. Why would this be a low-hanging fruit to make new friends? 

While hosting a dinner party takes effort, it’s one of the highest-ROI things you could do to nurture new friendships. Why? 

  • Dinner parties are more intimate than the usual social events, which helps people connect on a deeper level 
  • Guests will naturally pay attention to you, since you’re the star of the party 
  • You have the opportunity to bring interesting people together, which dramatically increases your social brownie points

If you’re interested in hosting a dinner party, here are a few tips that have worked for me: 

  • Start small. Start by inviting one person to dinner. Then, invite them and another friend of theirs. Once you’re comfortable, invite two people to dinner, each person would bring a plus one… you get the idea.

  • Outsource cooking. Cooking and hosting at the same time is a Herculean feat. Just order pizzas, or turn your dinner party into a potluck.

I recommend checking out Jon Levy’s TED talk about how he invited influential people to his dinner parties.  

Alright, moving on — here are a few ways you can meet people and make new friends in Chicago.

4. Meet fellow entrepreneurs, freelancers or remote workers

Join a coworking space

Given the open office nature of coworking spaces, I’ve found it much easier to strike up conversations — even while soaping my hands in the public washroom! 

Here are a few coworking spaces that others have rated highly: 

Most coworking spaces are connected to cafes. I’d approach people when they’re relaxing with their coffee or lunch i.e. when they aren’t furiously typing away.

10 easy ways to talk to strangers at a cafe

Join a professional association

You could also join a professional association to meet industry peers, or peers from the same backgrounds. Here are a few examples: 

See more on JobStars website.

Join an online community

If jumping into a coworking space feels too much at first, try online communities. Here are a few that I would recommend (still active, relatively spam-free)

Having co-founded and managed online communities of hundreds of thousands of members, here are a few tips to get the most out of whatever community/group you join: 

  • Be a star member: Regularly engage with other members’ posts, leave positive comments and offer helpful ideas when requested.

  • Take initiative: Depending on the community’s policies, suggest or organize events and invite other members to join.

  • Get to know the community founders/moderators: They will be more open to connecting than typical members, since it’s in their incentives to have an active community. Also, they would have the best grasp on who you should connect with.

Attend a business conference or networking event 

The biggest reason why people attend business events? 

To connect with others. 

Whether it’s learning from top experts, meeting industry peers, or finding potential collaborators, business event attendees are there to connect. Which makes it super easy for you to start conversations! 

Here are three helpful resources for you: 

5. Join a hobby group (or create your own)

If you have the same hobby, you have a natural topic to spark conversations with. 

This isn’t a complete list by any means, but I picked out popular hobby groups that are still active i.e. organized events in the last month or so. 

29 hobbies conversation starters to spark meaningful conversations

Create your own hobby group

Being a Meetup or Facebook group founder gets you in the spotlight, which can help you make friends faster. 

Join a festival, or volunteer at one! 

Here’s Eventbrite’s list of upcoming festivals in Chicago.

Some festivals also accept volunteers, like Old Town Art Fair and Chicago Humanities Festival. 

6. Sweat it out together! 

Working out together helps you bond better (see research here). 

You could join group fitness classes or specific sports groups – see below.

Group fitness classes

You could also explore various gyms by getting a Classpass subscription.

8 easy ways to talk to people at a gym (without being creepy)

Dance classes

Call me biased since I’m an amateur dancer, but dancing is such a fun way to make new friends — it infuses playfulness into your social interactions, which isn’t always the case in other environments.

If you have two left feet, no worries! Join beginner classes or get a private tutor. 

Sports/fitness groups 

7. Be a volunteer 

Similar to joining a hobby group, volunteering helps you meet like-minded people. A study shows that volunteers have more social connections than non-volunteers.  

In fact, connecting with someone who believes in the same social cause and engaging in meaningful experiences together will deepen your budding friendship.

Volunteer at a nonprofit 

While it’s by no means comprehensive, here’s a list of local nonprofits that I found most interesting: 

  • 826CHI: “826CHI is a nonprofit organization dedicated to supporting students ages 6 to 18 with their creative and expository writing skills and to helping teachers inspire their students to write.”

  • Lumity: “We’re Lumity, a STEM nonprofit building a future where STEM education is more equitable, accessible, and uplifting for Chicago’s under-resourced students. Build it with us.”

  • Step Up: “Step Up is a mentorship nonprofit providing the structure for girls (and those who identify with girlhood) to define their ideal destination and get there — wherever that destination may be.”

  • Gilda’s Club Chicago: “Gilda’s Club is a place where men, women and children whose lives have been impacted by cancer, as well as their families and friends, can feel they are part of a welcoming community of support. Join us and Take on Cancer Together.”

    Similar organization: LUNGevity Foundation
     
  • Chicago Parks Foundation: “Our mission is to build a stronger community dedicated to supporting and conserving our city’s parks.”

You can also search for the most recent volunteer opportunities here. You can also volunteer with the city of Chicago — they have a wide variety of programs. 

Volunteer at science/culture centers  

8. Join a religious/spiritual organization

Going to the same place of worship? Chances are, you will end up becoming friends… or even romantic partners 🙂  

As this study noted: “…religious service attendance is associated with an increased likelihood of subsequently making new friends, of marrying, of having nonreligious community membership, and of higher social support”.

Here’s a list of popular faith-based/spiritual organizations: 

9. Connect with people who are also ready to connect 🙂

Duh! So obvious right? But if you think about it, the success of new friendships depends on something most people — including myself — would hate to admit:

If the other person is interested in talking too.

That’s why it can be underrated to join general social groups, where people meet to simply connect and have fun. Embrace serendipity and check out these groups: 

10. Talk with strangers in community spaces

Talking with strangers can be terrifying. 

So how can you minimize the risk of social rejection?

Based on my experience approaching thousands of strangers, here’s a favorite tip of mine:

Talk with people who are not in a rush! 

Whether they are window shopping or admiring nature, they will be a lot more likely to engage in conversation.   

Here are a few community spaces that I recommend checking out: 

Artisan/farmers’ markets

Community centers 

Community gardens

I picked out the ones that have been highly rated:


See other community gardens on on NeighborSpace’s website (“NeighborSpace is the only nonprofit urban land trust in Chicago that preserves and sustains gardens on behalf of dedicated community groups.”)

Parks

See other parks on Chicago Park District‘s website. 

6 easy ways to talk to strangers at a park

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