(VIDEO) – Chicago Road Trip Captured Two Ways

While blog posts about our itinerary are nice to share, nothing really beats seeing real human interaction. Itineraries are a great way to know where we went, but I think videos are a better way to get to know the people behind these itineraries. Although we may travel on the same trip, see the same sights, eat the same food, and laugh at the same jokes, what is memorable to one person might be completely different to the other.

Part of SYDE Road’s goal is to allow us to see a trip from multiple angles, different authors, and different photographers. With this in mind, Angelo and I made not one, but TWO video summaries of our road trip from Toronto to Chicago.

It was a fun challenge to see what kind of videos we could come up with at the end of the trip.  Armed with a couple dozen 1-minute footage clips, we each cobbled two different narratives for you to enjoy:

    • Dancing around Chicago’s backdrop
    • What we actually do as tourists

Videos after the jump!

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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 coordinate 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 – what we might call an “SYDE trip” if you will. Thanks to Family Day, we had a long weekend here in Ontario. So, a different group of friends and I decided to take a road trip to Quebec City and Montmorency Falls.

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Travel Lessons – What I Learned When I Traveled to Montreal

Lessons I Learned When Extending Work Travel for Vacation

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 lessons that I learned when I traveled to Montreal for a work/play trip combination:

  1. Stay flexible with your trip options and be alright to go on an unplanned trip
  2. ‘Lost time’ or things that feel like they’re a ‘waste of time’ aren’t always a negative thing – you can make it a positive experience by changing your perspective
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