#33 Plan a spontaneous trip.

It’s Day 2 of my mini detour into self-directed acts of kindness, and I’m already feeling a bit more like my old self.

The concert last night was absolutely amazing. We decided to take an impromptu rickshaw ride through Toronto to get to the venue, and as I laughed so hard that tears streamed down my face, I realized that despite a rough few weeks, things are generally on the up and up. And that rickshaw is an undervalued mode of transportation – watch out, Uber!

I woke up today deciding I wanted to plan a trip somewhere. I have a bad case of wanderlust, and I’m never happier than when I’m sitting in an airport, passport in hand, ready to go off on an adventure. (And I’m never more miserable than on the airplane ride home, drowning my sorrows in mini bottles of gin and watching Casablanca for the umpteenth time.)

One of my friends is currently on a business trip in Chicago, and as he texted me colourful photos of deep-dish pizza and “the bean” throughout the day, I knew it is where I wanted to go. So I texted my best friend:

“Hey. Can we got to Chicago for my birthday weekend?”



Please take note: This is why my best friend is the shit. She doesn’t question; she just goes with it. Every time. A nearly-identical text message exchange has taken place preceding our trips to Las Vegas, across 12 European countries and most recently, Bali. 

I went online, booked our plane tickets and hotel – all in the span of 10 minutes.

Chicago, here we come!

Total Kindness Cost: $600 (ish) each

Anyone have any must-sees for my trip to Chicago? Holler!



    • Yay! Thanks for sharing. I never thought of doing the “hop on hop off” bus but that’s a great idea.

      Also, that pizza looks UNREAL. My stomach legit gargled looking at that photo. 🙂

  1. I don’t know how you feel about architecture, but Chicago really embraces their architectural history. Take a boat tour on the river (I hope your birthday is on a warm-ish day) and then go out to Oak Park, the Robie House and other beautiful Frank Lloyd Wright houses, churches and buildings. Chicago is definitely my favorite city in the United States!

    • I dig architecture. I’ve heard the boat tour is a “cannot miss” so will definitely check it out. I also just actually read a book based on Frank Lloyd Wright’s life so looking forward to taking it all in!

      Thanks for stopping by and commenting – I’m super excited now!

  2. I went on a weekend road trip last weekend. A friend of mind visited and we decided to take a 10 hour bus ride somewhere south of my country (Philippines). The best travel adventures, as I have often experience, come from the most impromptu planning. Have a blast in Chicago! It’s one of my favorite cities!

    • That is awesome that you guys did that!!! Love it. Thank you and I’m sure it will be a blast. So many people love Chicago.

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