Giving Back: A Skyscraper Adventure and Popcorn Finale

I founded Well Traveled Kids eight months ago with a two part mission:

  1. To host a diverse group of guest contributors who could serve as a great resource for families looking to travel well together, and
  2. To bring travel to less fortunate kids, who wouldn’t necessarily have opportunities to see the world.

Having successfully attracted and featured more than 20  talented guest writers on the site, I am eager to kick off our philanthropic efforts.  My pledge is to donate 50 percent of any profits to provide exploration and travel opportunities to less fortunate kids.

Though the site isn’t profitable yet, my husband and I funded Well Traveled Kids’ first trip for a group of special needs students in grades 9-12 from Johnson College Prep High School in Englewood, a neighborhood known for its poverty and violence on Chicago’s South Side. These kids live in a neighborhood where they can see the skyline of Chicago, but most have never been in any of its skyscrapers. I wanted to make that experience possible.


Working with their Special Education teacher, Lauren Feldman, who is also my husband’s cousin, I planned a day trip to the top of the tallest building in Chicago (and one of the tallest in the world): the SkyDeck at Willis Tower, formerly known as the Sears Tower, followed by a walk to the world-famous Garrett’s Popcorn shop for a delicious signature Chicago treat. We scheduled the trip for their last day of class for the school year, as a celebration and a fun way to start the summer.

A big part of these students’ education is learning to navigate on their own after high school, so this experience gave Lauren an opportunity to teach them life skills needed to navigate the city.  Lauren and her assistant teachers helped the kids develop individual budgets for their journey, load their own transit passes, catch the L train, and reserve money for popcorn later.


When the kids stepped off the L, they walked five blocks through the bustling downtown Loop to our meeting spot in the lobby of the Willis Tower. I waited for them there, along with my 4-year-old son Harry and my mother, a retired high school teacher. The morning weather was incredibly foggy, and as I spotted the kids walking up the sidewalk toward us, I couldn’t help but feel a little disappointed by the lack of visibility. Would we even be able to see anything when we got up to the Skydeck?

Harry, on the other hand, was immediately excited to see the kids. The kids were equally excited to be out of school and experiencing downtown Chicago. My apprehensions evaporated as we all entered the elevator, and I saw their eyes grow wide at the numbers racing past: floor 20…30…60…95…103.


We all spilled out of the elevator on the top floor, and I could feel the nervous excitement as we approached the Skydeck ledges—enclosed glass overhangs that give visitors a chance to, literally, stand over the city below.


We couldn’t see a thing except clouds of fog out the windows, but that ended up working to our advantage. The clouds made it easier for the kids to take that risk and step out onto the ledge. Some paced a little at first, but within a few minutes they were all urging each other to try it out … to take this step they’d never imagined.


As they crowded in shoulder-to-shoulder, a student in his wheelchair rolled over to see what being out on the ledge felt like. But he decided that wasn’t enough; he wanted to feel it below his feet and to sit directly on it like everyone else. I was touched as I watched the students join together to help him out of his wheelchair. They eased him to the ground and sat around him in rows, giggling and posing for photos.

Moments later, I spotted another student lifting Harry on to his shoulders so they could explore the Skydeck together. It was magical to watch Harry bond so quickly with these kids.  I had hoped the students would get a lot out of this experience, but I hadn’t anticipated how much Harry and I would benefit from spending a morning seeing the city through the eyes of kids who had never spent time in a skyscraper or walked through the loop. Weeks later, it still warms my heart to think of what an amazing day we had together.


My mom, who had taught high school for over 20 years, was also impressed by the warmth and gratitude of the students. She had warned me leading up to the trip of the myriad things that could go awry. “You don’t know what it’s like,” she said, with good intention. “High School kids can try to pull a lot on a fieldtrip.”

By the end, she could not believe how well-behaved our group of students was, how noticeably affected they were by the entire experience—walking from the L to the Willis Tower, riding so high in an elevator and stepping out onto a glass ledge.


After the excitement of going to the top of Willis Tower, visiting Garrett’s for popcorn was a really fun way to end the day. Each student was paired with another and had $20 with which to place their popcorn and drink orders and get change—all real-world, everyday interactions to help build their life skills. Harry was paired with one of the kids too, and she took her role as his partner very seriously as she proudly held his hand and ordered for him.

From Garrett’s, we crossed the street and found a spot in the sun to sit and eat our popcorn together. We relaxed, took in the people around us, and sang songs from what we discovered was our shared love—the hit TV show Empire.

Then, the kids headed back to the L station, where they loaded their cards and returned for their last afternoon of classes. Some had finals in the coming days; others would graduate that night.


For Harry and me, it was unforgettable. Harry still asks his cousin Lauren about all of her students, and together we read through the emails they sent thanking us for the excursion –for such a good time, recalling the adventure, the popcorn, and the conversations.


One note read, “Dear Sarah, Thank You I have a good time with your mom and your nephew and we was having a card for you and I use my manners for being a nice person that I am. And we went to Garrett’s popcorn and it was delicious and we also went to the skydeck store and they got alot of cool stuff there and it was fun.”


Another student wrote,”Dear Sarah, I want to say thank you for taking us on a field trip. We had a very good time with you and son. We hope that we see you again.

My favorite email said, “Dear sarah,i had so much fun at the sky deck and I had fun eating popcorn and having a conversation about Empire.”

The experience reinforced my commitment to giving kids from all backgrounds opportunities to travel—even a seemingly small school field-trip in their hometown gave kids a chance to get out from their usual routines and see the world around them.

I also resolved to continue bringing Harry along on these adventures as much as possible. They will give him a chance to see another perspective of the world. He got a vastly different view of Chicago than he usually has, and to me, that’s more meaningful than any hotel stay.

Meanwhile, I keep thinking of the kids riding in the super fast elevator up to the 103rd floor. They’d been so quiet on the way up, nervous even. But on the way down, they were energized, unable to stop talking about everything they’d seen and tried for the first time. Even though Harry and I had both been to the top before, on this day we all had that in common.

photography by Katie Scarlet Brandt

Sarah Hirsch
Sarah Hirsch

Sarah is a Chicago-based luxury travel influencer, Virtuoso luxury travel advisor, luxury family travel writer, an Oprah Daily Ambassador, and the founder of Sarah’s best travel companion is her sweet 12-year-old son, Harry. Her favorite getaways include a luxe hotel stay, quality family playtime, champagne & chocolate-covered strawberries.

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  1. July 29, 2015 / 10:36 am

    Now I know what “Well Traveled Kids” is all about. I don’t think you explained it in the early stages on Facebook.
    Best wishes,
    Uncle Alan Hoffberg

  2. August 2, 2015 / 10:53 am

    What a beautiful mission and story!! I also hadn’t picked up on your goals for Well Traveled Kids and I’m so impressed with what you are looking to do. That must have been a rewarding experience for all.

  3. August 2, 2015 / 11:41 am

    What a fantastic post and what a terrific thing to do – you obviously had a brilliant time, which is wonderful and the smiles say it all!

  4. August 2, 2015 / 8:15 pm

    I love that it teaches life skills. It should be a way larger part in the school system.

  5. August 3, 2015 / 11:48 am

    What a fun day! Kudos to you for organizing such a fantastic experience!