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When my team and I got invited to host an event in Chicago, I was thrilled for a few reasons. First, there was the event itself. I launched Career Contessa, an online career platform for women, over four years ago, and it’s since grown into a thriving startup with six full-time employees. This was going to be our first in-person event series—a welcome and exciting challenge, not to mention an incredible opportunity to meet the readers who’ve followed us for so long.
Then there’s the fact that Chicago is an amazing city that experiences a picturesque fall season while our homebase of Los Angeles is still struggling to drop to temps lower than 90 degrees. Finally, it was the first opportunity for our whole team to travel together, and I was excited for all the cliché team bonding experiences it promised.
As a startup, we’re always looking for ways to multitask—and ways to save money without sacrificing quality. So, with five of us traveling to Chicago for four days for our Power of We event, I knew an Airbnb rental would be the most cost effective housing option, but it would allow us to successfully mix business needs and our collective desire to live like locals in a new city.
I had a few criteria when booking an Airbnb, especially with regards to location and space. I wanted us to stay in an established neighborhood with charming restaurants and plenty of character. I also wanted to make sure we all had our own room. A 5-bedroom house in Old Town, a neighborhood just an $11 ride from River North (where our event would be held) checked all the boxes—including its walkable proximity to shops and restaurants. The house was spread out over three levels so everyone had plenty of private space, but there were also two communal areas and a large kitchen for daily gathering—and dedicated work time.
Work and emails don’t stop just because we’re gearing up for an event. Because we publish content daily on Career Contessa and juggle multiple social media accounts and email channels, it’s important for us to keep to our routine including all the necessary weekly meetings. So, we did exactly that. We used the communal areas to work on our individual task and turned the kitchen into our “meeting” room. The change of scenery helped us managed our time and tasks. I should also mention the kitchen and living room with a fireplace are a future homeowner’s dream…so we took advantage of the homey amenities by preparing snacks and working next to a crackling fire.
But it wasn’t all work and no play for us on this trip. We made sure to experience all the parts of Chicago we don’t have in LA. We rode the “L” to grab bagels and coffee in Lincoln Park, took advantage of the sun one day by walking down Magnificent Mile in the late afternoon, stopping to check out the lobby of the Tribune Building and for photo ops along the river. We made sure to eat at a variety of different neighborhood establishments: Nookies, Twin Anchors, and Kanela. By far one of our favorite activities was walking down the tree-lined streets admiring the fall colors, crunchy leaves, and the perfectly decorated front door stoops.
Our time in Chicago was the workcation we all needed and deserved after the hard work it took to throw a successful event with over 80 attendees. We bonded, we explored, we recharged, and we’re all going home with increased excitement for the next team outing. Renting an Airbnb over a hotel was the tipping point that made this trip unforgettable.