Fortunately, I don’t have to travel for work often. With my values rooted in family and time spent together outdoors, I don’t think I’m cut out for the type of work that requires me to be on a plane more than a couple of times a year. That said, when it does come up and I do have to be away, I try with purpose to locate the moments to make it worthwhile.  It’s not that I can turn the job into a vacation, but I can put in the effort to step outside the hotel room and find a good bit of food, some music, a local landmark, an art studio, anything I can sink my teeth into that couldn’t be found back home.  This most recent stint away, however, I decided to extend beyond the required work obligations and make it a little mini vacation.  If I had to be away in a city such as Chicago, then why not take the time to explore it?  And if I’m going to explore it, then what better way than to do so with the greatest adventurer and travel partner I know?

In the spirit of adventure, rather than spending the 10-hours of travel time in and out of airports, Alison and I opted to charge up the car and spend those 10-hours driving across the border instead.  Something about being in a car with constant forward momentum has far more appeal to me than sitting idly in an airport…waiting…hoping you don’t get delayed….and then sitting again in a very cramped space with bad food, bad air, and bad smells.  Making that drive allowed for whatever stop along the way that we deemed most appealing, appetizing and attractive.  Granted, making such a trip with a fully electric car does mean you need to take some planning into account, but the infrastructure of charging stations is almost as ample as that of the traditional gas station, so it really didn’t feel like an interruption to our plans in any way.  Plus, getting out to stretch the legs every couple of hours was a ore than welcome reprieve.

Now, I had been to Chicago before – last year, in fact, for the same work-based event this year, but, whereas during my previous visit I was alone, this visit was one I was very much looking forward to.  Very early into our relationship, Alison and I took a road trip to New Orleans to take in a music festival.  It was on this road trip that we truly fell in love.  Spending that time together to learn just how in sync we are with our passions and values when it comes to travel truly sealed the deal for both of us.  Eat.  Drink.  Explore.  We both showcased our desire to try local, experience new, and take it all in.  We also discovered just how compatible we are in our waking hours – neither of us being able to stay awake past 10:00 to experience ‘night life’, whatever that is.  We enjoy happy hour, love to hike, and believe in a loose itinerary vs. anything strict.  We have taken many trips since then, but it will always stand out to me as the one that paved the way to the rest of my life; so getting to spend a couple of days in The Windy City together, well, there’s just no going wrong.

It rained.  Like, a lot.  With only two days together, when one of them turns into a 12-hour downpour, it’s kind of a bummer.  When the Jays/Cubs game we had tickets for was cancelled, that was more than disappointing.  When every restaurant we tried to eat at decided to close early due to the rain, or was out of the preferred on tap selection, that was just a kick in the ribs.  At least it would be for most.  For us, however, no matter the situation or what gets thrown at us, we do our best to make the most of it.  Sure, we are still bummed, pissed off and disappointed, but we will use one change in plans to create opportunity for others.  I may not have had the chance to see the Blue Jays play at Wrigley, but I did get to see a local theatre troupe perform a drunken version of Romeo and Juliet…a highly inappropriate and hysterical showcase of talent, comedy and sex toys where the lead in the play gives themselves over to a half dozen shots of whiskey before the first act.  It was a bit of entertainment that we weren’t fully prepared for but, as far as experiences go, it was certainly one of a kind.

Entertainment, dining and shopping aside, the best part of going anywhere with Alison is the openness to simply explore by any means possible.  While we may anchor our day with an event to look forward to, the best of our time is spent by foot, train or bike venturing up and down neighbourhoods until something piques our interest.  Fun looking park?  Let’s go down the slide.  Outdoor rock climbing?  Pass me my harness please.  Bike rentals along the waterfront?  Who needs a helmet?  The most exciting element of any adventure, at least to us, are the conversations we have to and from the various unknowns and special discoveries that no amount of planning could have unearthed.  I love that the time we spend together continues to provide conversations – all these years in together and we still haven’t scratched the surface of this planet.  As far as adventures go, this life with her is always full of excitement.

Of course we took to the touristy things that one must embark upon when in Chicago.  We saw The Bean, we ate the Italian Beef, we admired the architecture, we went to a Jazz club, and we hit Navy Pier, among so much else.  It was an interesting tour through the area, as we found ourselves comparing the city to Toronto and trying to decide if back home has as much to offer and if we’re just blind to it.  We ultimately couldn’t land on a decision there, though it did prompt us to consider picking up a Lonely Planet Toronto this summer.

Maybe that’s the biggest take away from all of this – that perhaps one doesn’t need to travel far to discover something new. That it’s not really about Chicago, New Orleans, or wherever we happen to find ourselves next. The destination is simply an excuse to wander together – to stumble into conversations, share a meal or a show that we’ll talk about for years, and remind ourselves that the greatest adventures aren’t about the place…but about the person standing next to you.