The first time my kids flew to Japan by themselves I was a little nervous. They’d done the trip a few times before, but never alone. It was my first winter as a single mom and I was used to traveling with my kids but this year they were going to visit their on their own. Their flight had a stopover in Chicago, so I decided to fly the first leg of the journey with them.
One of the biggest shocks to my system as a newly single mom was getting used to not having my kids all the time, and letting them do things like fly across the world by themselves. But as I have come to learn… there are good and bad aspects to everything.
The stopover in Chicago was less than an hour so timing was tight. Our flight from Toronto was late, so it was a scramble to get them from gate to gate.
The kids had their carry on bags with them so they were ready to run, but mine had been checked in so I needed to wait. An airline personnel rushed to get my kids to their next flight while I stayed and waited anxiously for my bag.
It took about 5 minutes for my bag to come out, but as soon as it did, I grabbed it and ran. People must have thought I was a crazy woman sprinting through the Chicago airport, dodging carts and leaping fallen luggage with a frantic look in my eye that only a mother who has lost her kids could have.
When I got to the kids gate, my kids had already boarded and were waiting for takeoff. They actually sat on the runway for a good 40 minutes while I paced back and forth inside the window looking out and waving madly at the plane in case they happened to look my way.
It was a relief to get that over with. When the plane finally took off, I had no choice but to relax. And realizing I had two days to myself in Chicago, I calmly made my way to the train. I was pleased to discover that Chicago has one of the best train systems for getting from the airport into the city I have ever seen. If I remember correctly, the one way fare was about $3 and in under an hour I was in central Chicago.
I had booked a room at the Freehand Chicago (through booking.com) for $27/night and it was great. I had one of four bunks in a clean, friendly female dorm. Each bunk had a curtain that you could pull across for privacy, so with my earplugs and mask, I was set.
The downstairs of the Freehand Chicago was a lively bar in the evenings, and a funky cafe in the day. It was within walking distance to everything so I spent the next day walking around Chicago’s art galleries, shops, and millennium park, and the night discovering some of the city’s thriving jazz spots.
It was a two day getaway and a glimpse into what was possible as a single mom traveler. And I was excited to be finally feeling back in travel mode and on the right path.
A week later, I would fuel my wanderlust further and book a last minute trip to Mexico.