Road Trip to Chicago from Toronto – Four Day Itinerary

B&W "Bean" in Chicago (Cloud Gate)

You’re going on a road trip to Chicago from Toronto? …. You should always takes the Detroit-Windsor tunnel over the Ambassador’s Bridge

…were the first word’s that my friend, and fellow SYDE classmate uttered as soon as I casually mentioned that I was going to go on a road trip to Chicago from Toronto.  According to his co-workers who regularly traverse the Detroit-Windsor border, the tunnel is hands down better than the Ambassador’s Bridge. The line is shorter, it is cheaper than the bridge, and the border checkpoints are faster.

So far, I’ve been really lucky that with each destination I go, someone I know either knows another person who has made the same trip before, or has done the trip themselves as well. Regardless of the situation, I’ve always received warm words of advice that has made each vacation smoother and more enjoyable. Any advice to get to our destination a little faster was much appreicated – especially since driving from Toronto to Chicago is already an 850km  (~530 mi) journey one way.

Kent was off in Vancouver during the same week I decided to go to Chicago and Anson was well… doing whatever he does best in Seattle (most likely climbing mountains) so this road trip was another SYDE Dash from the main group again.

This was an aggressively planned “see as much of Chicago in four days while breaking Maria’s 2 hour driving limit threshold”.

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Quebec Road Trip Costs – How I spent only $75/night

How I only spent $75/night on my road trip to Quebec

Oftentimes, vacations would cost me upwards of $1,500 for one week, or approximately $214/day. Unless I somehow double my income, I’ll have to limit myself to having a maximum of one of these vacations a year. So how can I go about incorporating more travel vacations in a year without breaking the bank? Now, I haven’t been tracking the costs of my vacations in detail. Most times, I’m only aware of the final cost of the trip itself. As an experiment, and as a way to start figuring out to have more vacations for less, I started to track how much my Quebec Road Trip cost.

Surprisingly, after all the finances were balanced out, I only spent $75/night!

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Quebec city and Montmorency Falls – Unplanned Road Trip

Winter view of the panoramic stairs near Montmorency Falls

Anson, Kent, and I don’t always travel together. The combination of time zone differences and drastically different work schedules make it difficult to co-ordinate a trip together. All of us still get the itch to travel so we’ll go off on our own individual side trips without each other – a SYDE dash trip if you will. Thanks to Family Day, we had a long weekend here in Ontario. So why not take a road trip to Quebec?

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Travel Lessons – What I learned when I travelled to Montreal

Natrel Fireworks as seen from Mont Royal

Every vacation can provide valuable lessons that we can bring forward to our future vacations and trips. Be that experience a pitfall and learning to avoid them in the future, or scheduling more down time, there’s always something we can take away from a trip beyond good memories.

There are two main concepts that I personally learned from our Montreal work/play trip combination:

  • Staying flexible with your trip options and being okay with unknowns might bring new and unexpected memories
  • ‘Lost time’ or ‘waste of time’ actions aren’t always a waste – it all depends on perspective

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Montreal and Mount Tremblant: Mixing Work with Play

Snowmaking machine and the morning sun on Mt Tremblant's trails

It all happened so fast…

A brief conversation about work, a clink of a few cups of green tea, a critical email, a chat, a quick visit to Liftopia.com …and just like that, we found ourselves in a car at 8 am on the first Saturday of 2017 driving east to Montreal with a receipt for one day pass ticket to Mount Tremblant in our inboxes.

The trip started out as an offhand idea thrown around while sipping tea in someone’s dining room. I don’t think we imagined that our little chat would ever become anything more than a daydream. Since mid-December, my company has been ‘maybe’ thinking of sending me to Montreal for training in the second week of January. This would be the first time I would travel since onboarding training and I was anxious to ensure that it would happen. What a great way to start the year! What would be even more amazing was if I could somehow incorporate a mini-vacation with this too. We’ve lamented in the past over how work travel perks (e.g. sending your ‘spouse’ aka friend over to visit the client’s city) could be better utilised. This conversation was no different.

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