I Flew to Chicago to Meet 30 Strangers From the Internet: Here’s What Happened

In the heart of 2021, amidst the lingering echoes of a world paused by a pandemic, I embarked on a journey to meet up with a group of people I found online and was rewarded with the warmth of newfound friendships.

In theory, I was doing everything my middle school teachers taught me not to do.

The concept of forming profound bonds without ever meeting in person might seem peculiar to some. Yet, here I am, recounting a tale of how a simple app called Clubhouse led me to venture into the Midwest to meet a group of “strangers” from the internet.

Meet the Traveler’s Chill Lounge (TCL)

These were no ordinary “strangers”, though; they were friends I had made through my phone in a virtual Clubhouse room we fondly called “The Traveler’s Chill Lounge.”

It was September, a time when the digital corridors of a social audio app called Clubhouse still buzzed with life, helping bridge the gaps of isolation we faced during the era of social distancing.

A Nostalgic Trip Down Clubhouse Lane

For those unfamiliar, Clubhouse burst onto the scene as an invite-only audio chat app, creating a buzz for its novel and exclusive approach to social interaction: social audio.

Essentially, Clubhouse was a way for users to enjoy voice-based group discussions in digital rooms where discourse would generally revolve around a specific topic noted in the room’s name.

A lot of the initial buzz surrounding Clubhouse revolved around the presence of notable public figures and celebrities using the app to make spontaneous guest appearances. If you had an invitation to be on the platform, you theoretically also had a shot at having a conversation with these people directly.

I still remember the moment I was invited to join, I was so excited to begin a new challenge. Initially, I used Clubhouse to practice public speaking, something that I found a bit intimidating as an introvert.

Clubhouse Lingo

The lingo itself was a world of its own – phrases like “let’s reset the room,” “PTR” (pull to refresh), and more. Since I’m already reminiscing, let’s dive a bit deeper into Clubhouse Lingo (please note: this is based on 2021 lingo, since that was when I was primarily active on Clubhouse.)

At times, it felt like learning another language:

  • PTR (Pull to Refresh): Swiping down to update the room. This refresh would update and reorder the sequence of speakers in the room.
  • Room: The core of Clubhouse, a room is a space where conversations unfold based on a specific interest. You could silently listen in or ask to participate in the discussion on the stage.
  • The Stage: This is the section of the room where the speakers are. Room moderators, with the power to invite audience members to speak, automatically occupy this space by default.
  • Mods (Moderators): The individual(s) who control the room’s conversation, identifiable by a green star next to their name.
  • Party Hats: Sometimes referred to new Clubhouse members, notably because of the party hat emoji that appears beside your name during your first week on the platform.
  • The Hallway: The main landing page of the app where you could find and join rooms based on your interest.
  • The Waitlist: By signing up for the waitlist, you secured your username while waiting for an invitation from an existing user to invite you to join Clubhouse.
  • Ping/Pinging: Inviting someone on Clubhouse to join your room by clicking the + icon and clicking their name. This notified them to join the room you were in.
  • PTR Order: Refers to the arrangement of people on stage after refreshing your room through PTR, ensuring the correct order is maintained for rooms with a large number of speakers on the stage.
  • Silent Rooms: A room where members remain silent or play music while working individually.
  • 24, 48, 72-Hour Rooms: A room that doesn’t close for a specified amount of time. As long as someone remains in the room on the stage, the room remains active. (TCL did one of these!)
  • Town Hall: Meetings hosted by Clubhouse founders Paul Davidson and Rohan Seth, where they’d take questions and share updates about the app.

TCL Became A Tight-Knit Online Community

Night after night, I would join the Traveler’s Chill Lounge room to join in conversations about a myriad of topics. From discussions about the best Chipotle burrito combination to the ultimate credit card for frequent travelers, there was never a dull moment in any of our nightly rooms.

The best part was how inclusive the app felt: simply by virtue of joining a room, you’d likely be invited to join the discussion.

I fondly remember one of my favorite aspects of TCL Clubhouse culture was this “mad dash” to join right as the founders (Lucie and Chelo) would open the room. It was a friendly rivalry to see who could get brought up to the state first.

It was this same group I’d soon embark on a adventure to go visit in the great Windy City of Chicago!

Some of the TCL faces in the photos you’re seeing may even look a bit familiar to you! (Like Kamyar and Lucie, from the photo above.) This is the same travel group that I’ve since attended and written about other meetups with!

You may recall reading on my blog about the time we visited the new Centurion Lounge in New York City.

An Unforgettable Journey: From Stormy Skies to Chicago Highs

The night before my flight, Hurricane Ida unleashed its wrath on New Jersey making me nearly miss my flight to Chicago! 😨

The Storm Before the Calm: A Pre-Trip Like No Other

Every adventure has its trials. Mine began with facing Hurricane Ida, a tempest that unleashed its fury upon New Jersey the night I was scheduled to depart for Chicago. Transforming streets into rivers and my plans into uncertainty, I had no idea what might happen as I packed my bags for my 4 AM Uber ride to the airport.

You can imagine the chaos as my scheduled Uber for a 4 AM pickup cancelled and left me stranded, watching the clock tick closer to my flight’s departure time. In a desperate bid for a ride, I paid triple the price for a life-threatening Lyft ride.

Thankfully, I found a brave soul who navigated through apocalyptic landscapes with flooded highways and overturned cars to get me to Newark Airport where the entire first floor was under water.

How my airplane took off on time at 9 AM is a true mystery, but miraculously… I made it safety to Chicago.

Flying During the Pandemic

Since we’re already reflecting on events from the past, I’m looking back at photos I took while flying and I’m reminded of what an unbelievable time we lived through. I am so grateful that this is mostly behind us, even though the world will likely always show signs of the COVID pandemic.

Arriving in Chicago: Making the Leap from Digital to Real Life Friends

Against all odds, I arrived in Chicago, a city unmarked by the chaos I left behind. The first friend I met friend TCL in real life was Henry!

We crossed paths at the airport and traveled together to the hotel where we would be staying.

As we made our way to Chicago’s River North district, we found other TCL friends along the way like my animal-loving friend (and TCL roomie) Amy!

The three of us went to get ramen for lunch together while awaiting the arrival of the others.

The best part of this meetup was that there was no awkwardness. Even though I was meeting everyone in our group for the first time in real life, I felt like I knew everyone already. I guess that is what happens when you talk to a group of people every single day, even if it is through a phone!

The Heart of the Adventure: Exploring Chicago

Our days in Chicago were a whirlwind of discovery and delight. We saw so much during the days we spent together so I’m going to give you a mostly photo and video-based overview of all the main places we went!

Let’s go:

The Bean

Laughter filled the air as we posed together for photographs at Millennium Park and The Bean. Our reflections warped in the Bean’s shiny curvature as we walked beneath it.

Millennium Park

The Great Escape Room

The Deep-Dish Pizza Experience: Lou Malnati’s Pizzeria

Parlor Pizza Bar

Kingston Mines Blues Club

Havana Mojito Bar

The Chicago Architectural River Boat Tour

Mother Hubbards Sports Bar

A major highlight was finding this blue and gold macaw. While I was a bit concerned over the volume of the bar for the bird’s sensitive hearing, the owner was bringing him around for socialization purposes so we all took turns holding him.

It made me so happy since I haven’t interacted with a bird in so long. Probably not since my sparrows pre-pandemic.


Point and Feather

I’m not sure how we got into this VIP area, but we did…

Tree House Chicago

Wildberry Pancakes and Cafe

The Aloft River North

Our group stayed at the Aloft in River North.

One night, all 30 of us got together and hung out. I enjoyed those times.

Our TCL mascot:

Firecakes Donuts

I got a spicy donut! 🌶️

The Chicago River




The best spicy chicken. I wish Nandos existed back home.

Farewell Brunch at Punch Bowl Social

Airport Dinner with The Points Partner

On my way back home, me and my buddy Praveer had the chance to sit down with Owen, also known as The Points Partner, for a discussion about travel rewards credit cards.

Reflections & Farewells

I haven’t had the chance to go on many large group trips in my life. China in 2015 was probably the first one and then this Chicago trip was probably my second!

I’m really grateful to Lucie and Chelo, the founders of TCL, as well as to TCL members from the Chicago area who put in a lot of time, effort, and energy to make sure this meetup was a success.

Until the next meetup, TCL! 👋


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The Rocky Safari