On Day 3, we awoke before the sun.

Photo By: Sera Lindsey

Groggy, we filed out of the hotel into the chilly dawn towards Chicago’s tallest building, the Willis Tower. The streets were quiet and remnants of the night still pooled in doorways and around corners. There were no other people in sight and any cars that passed kept their distance, headlights weak in the approaching sunrise. It felt like we had the entire city to ourselves.


At the Willis Tower, we rode the elevator 103 stories high to Skydeck Chicago, where we were treated to spectacular, private views of the sprawling city below. Lights clicked on in the buildings below us one by one as more cars gathered in the streets far away on the ground. The whole city appeared to be struggling to rise from its slumber.

A hint of light revealed itself on the horizon over Lake Michigan. The sky seemed to be waking up ever so slowly, and with it, the excitement of our group. With a quickening pace, the warm yellows chased the dark blues higher and higher above the horizon and over our heads, racing further West. We gathered by the windows and on the ledges, almost pulled by the suns beckoning rays and lay quietly in the glass windows for a while, enjoying the privacy and the silence and the beauty all around us.

The afternoon brought a welcomed change of pace. At midday, over 100 people of all ages and from neighborhoods throughout the city gathered at Chicago’s legendary Bean for the Passport Express’ first Instameet. Together, we walked several miles through the downtown Loop, crossing the Kinzie Street Bridge to the West side of the Chicago river, and ending at Soho House on Green Street for a reception. We stopped along the route to marvel at unique architecture and play with light rays pouring through alleyways and train tracks, feeling like kids exploring a life-sized playground.

To the Chicago Instagram community, thank you to everyone who came out to join our group! We’re so grateful for your energy and support, and for the opportunity to meet so many new people who share in our passion for photography, creativity and community.

Photo By: Adrienne Pitts
Photo By: Sionnie Lafollette

Our day continued at the Museum of Contemporary Art, where we were privileged to have access to the empty museum after-hours. Just as the public left, we were welcomed inside, free to explore the exhibitions and the nooks and crannies of the space. We paid particular attention to the S, M, L, XL installation, which offered us a chance to experience works of art varying in scale. Our group’s favorite was the largest sculpture, made of a decommissioned hot air balloon. We ran though it, appreciating its size and vibrant colors, and the rare opportunity we had to have it all to ourselves.

This magnificent brought to us by our friends at 360Chicago.

And then, because we started the day with the rising sun, we decided to see its end with an epic sunset, witnessed from the windows of 360 Chicago, formerly the John Hancock Observatory, 1000 feet above ground. One of the Passport Express conductors, Ruthie, remarked: “One of my favorite parts of today was sitting with Katie Ann with awe and wonder watching the sunset. We both shed a few tears and talked about how every sunset feels like a gift. It’s a beautiful promise of a day closed, and the hope of a new day, a new beginning.” A giant group huddle led to everyone collapsed on the floor, basking in the final light of day. The mirror on the ceiling reflected our shared emotion, and we took a selfie to capture the moment.

Come along for the ride.

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The Passport Express