iPhone Photo Diary | Chicago, Illinois

When I started a new job last fall, we weren’t sure how much we’d be able to travel this year. And when he changed jobs again just before Christmas, our 2020 travel plans became even more uncertain. But travel is always a priority for us – and is becoming increasingly important as our work responsibilities increase to a point where we cannot shut off unless we are physically away from the office. So we scheduled a trip as early in the year was we possibly could – a quick four-day jaunt to Chicago. I am so glad we did. With Coronavirus-induced hysteria increasing at an alarming rate and likely to continue for the rest of this month at least, we would have run the risk of not being able to leave if our trip were even a few weeks later.

As of this week, I’ve cancelled all my work flights for the foreseeable future and we don’t have another holiday coming up until June. So I’ll be reliving our Chicago adventures for the next several months.

I visited Chicago for the first time in 2015. It was a girls’ trip, and we chose our destination largely because, out of a long list of cities, Chicago was the place that Ian was least disappointed to miss visiting. Little did I know. I arrived alone, very early in the morning and took the L train to the city, still half asleep. I couldn’t find my bus stop after getting off the train downtown and wound up hailing a cab. When it turned onto West Wacker Drive, the Wrigley Building coming into view with Tribune Tower across from it, I fell officially and irrevocably in love with Chicago.

I’ve wanted to go back ever since, but the timing and flight prices have simply never been right until this year. The wait felt long, but it was worth it, because we had the most perfect four days in Chicago. The weather was unseasonably warm and sunny, but hotel prices were low (because February) and tourist attractions were uncrowded. We were able to stay at a beautiful property we wouldn’t normally splurge on, which delightful.

And since it was such a short trip, we through caution to the wind (as much as we can. We – and I, especially, – are pretty naturally restrained.) We’re normally budget-focused on our holidays because we travel so often. But with only three full days in Chicago, we gave ourselves permission to absolutely enjoy our stay, whatever the cost. We took taxis. We ate every single meal out. On a longer trip, we couldn’t have splurged so much. We especially couldn’t have splurged on twenty dollar plastic cups of rose at the London House rooftop bar. Would I do it a second time? Probably not. But would I trade the experience of doing it this time? Not for anything.

Our Chicago trip really was a beautiful experience, and just what we hoped it would be. Looking back through these photos that I took on my phone, I can’t help but smile – and look forward to sharing more from our adventures!