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Goodbye Children Hello Chicago

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 my ex in Japan on their own. The flight he had booked for them had a stopover in Chicago, and since they were only 11 and 14, I decided to fly the first leg of the journey with them to sure they got onto the second flight safely. One of the biggest shocks to a newly single mom’s system, is getting used to not having your 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 would be tight. And as it turned out, our flight from Toronto to Chicago was half an hour late. Luckily, the second flight was also late taking off, but we didn’t know that so there was a mad 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. Since I was stuck, an airline personnel had to rush with 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, which seemed like an eternity, but I grabbed it and ran as soon as it did. People must have thought I was a crazy woman sprinting through the Chicago airport, dodging small families 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, they 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 (again, through booking.com) for $27/night and it was great. I had one of four bunks in a clean, friendly female dorm. There were two other girls in the room who were students on their spring break and one bunk was empty. Each bunk had a curtain that you could pull across for privacy, so with my earplugs and mask that I always travel with, 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 like I was on the right path.

A week later, I would fuel my wanderlust further and book a last minute trip to Mexico.

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