Cloud Gate Chicago
North America, Travel

All Business in Chicago

Cloud Gate Business in Chicago

Have you ever been drawn to a city before? I don’t quite understand it but I feel like I’m torn in a million different directions due to it. I don’t like big cities. I like my quaint, you can get everywhere in Austin in 20 minutes (without traffic) sized city. But for some reason I keep finding myself in Chicago and I’m not sure how I keep ending there. With my mind drifting between between London and Chicago, I feel like I have two mistresses, each beckoning to me at all times.

I got to go on my first business trip most recently. I have finally found a “Big Girl” job with WooThemes and they love me enough to invest in me as an employee. They paid for me to get out to Chicago to head out to UserConf – a badass tech customer service conference. Packing my suitcase I felt almost an adrenaline rush. Had I finally found that job? Had I finally been able to be paid to travel?

Holy shit. I have arrived. AND they were sending me to Chicago.

I didn’t really know what to expect my third time around. Shaun sat at home sulking a bit – Chicago being on his bucket list and I keep finding myself there – without my partner in crime. But from the moment I got off the plane and stepped onto the L, a grin took over my face. There is something magical here and I can’t quite put my finger on it.

Is it the fact there is nothing quite this urban at home? Is it the grimy charm? Or the interesting people?

The familiarity that came with my third visit just made me have warm fuzzies inside. Is it the beautiful architecture of downtown? Or winding through the steel beams after getting off the train? It is the gusts of wind and the rain kissing your cheeks? Or is it the intimate moment at the Cloud Gate as you reflected on the time you have spent there?

I think it is a little bit of everything.

A quick touch to the shiny bean and I was transported back in time to the first moment I saw it. The first lick of heat and the kids running through the Crown Fountain, trotting 2 miles during the summer while carrying film gear (I was shooting a short film), and driving into town with Diana from D Travels ‘Round. I’ve been here before, and I’ll continue to do so.

This time I got to see a different side. A business side, and I fell more in love.

This time I got to cruise around the bay, overlooking downtown at night. With the cold wind whipping around me on the hull of the ship, I still managed a quick shout of, “I LOVE CHICAGO!”.

I got to share a champagne toast with one of my besties, Maria of The Roaming Pint.

I got to take a break from work and walk on a brisk, cloudy day through Lincoln Park. What a hell of a view!

Oh! And I got to see Mike Tieso of the Art of Backpacking. Our spouses were green with envy. I love being able to catch up with good friends – AND I work with him now!

And beer.

…and the bean/Cloud Gate… again.

I even got to finish my time in Chicago with a quick Chicago Hot Dog breakfast before I caught my plane home.

It was over before I could even blink. But even after my business in Chicago, the one nagging feeling I had at the pit of my stomach was, while I love traveling, I would much rather experience it with Shaun. I had a fabulous time – but I was without my partner in crime.

As the plane landed, I couldn’t have been happier to be home in Austin, Texas. I had gone from the chilly, rainy 40s back into sunny, balmy 80s. Shaun drove up in our Subaru, hopped out, and pulled me close.

Yep. I’m happy to be where I need to be.

29 thoughts on “All Business in Chicago”

  1. Weeeeeee!

    Good times getting down to bidnizz! Happy you are blogging again and Woo can provide you with the satisfaction you’ve been missing with other jobs. 😀

  2. I love your love affair with Chicago and love that I was a part of it two years ago!! <3 What a cool experience to be there for business. I'd love to experience a city like that for a work trip, particularly if it includes beer, etc.

  3. Funny, since I grew up thinking of Chicago as “a place I go to see family” I never really had a love affair with it like this. I think it would be fun to go back now with my travel blogger hat on and see what it’s like through that lens. Congrats on the great new job!

    1. Yeah, I feel that way with San Antonio. I’m like, MEH. I don’t even know if I could get my blogger hat on there – to be honest.

  4. Totally agree with you on how awesome Chicago is. I have been there twice while on tour and fell in love with the city. We managed to play two different areas each time we were there. The food was incredible and so were the people. Can’t wait to go back.

    1. The FOOD. OMG THE FOOD!

      I love Austin because it is small. So when I head into something massive like Chicago, it is novel. 😛

  5. Chicago hot dogs are so weird but I love them. Or at least I did the one time I had one in NC of all places. Sounds like the new job is going really well, and I’m so happy for you! The new changes to your site look pretty good too!

    1. I’ve also been there in the summer and it wasn’t too bad – but I’m also used to Austin heat. 😛 I do love it during the summer. Very urbany.

  6. I was planning on visiting Chicago this summer but I signed up for a course and I don’t think I can afford it.. 🙁 I will make it there soon, tho! Loved all your photos, especially the one of water sliding down the bean. Awesome capture.

  7. Chicago is by far my favourite city to live in. I lived there for two years, and wish I could be back there everyday. Did you get to hang out in Logan Square by any chance? There are so many amazing bars there (I’d suggest The Whistler for great tunes and cheap craft cocktails, or Revolution Brewing) and restaurants! Let me know the next time you visit, and if you want any suggestions for places to eat/drink/debauchery!

  8. Crazy thing is I am always finding myself in Chicago as well and the first time was strictly by accident. On my 30th birthday I was flying to New York to see some friends (via Chicago) and of course my flight to NY got cancelled and I there were not flights for 8 hours that I could get on. So I decided to head in town on the train (which was very convenient from the airport) and celebrate my birthday. I ended up in this pub called Millers Pub and found that people in Chicago really love happy hour and being it was my birthday things got a little interesting. Long story short is if it was not for my flight being cancelled I would have never have looked at Chicago twice. Now I go back every chance I get and meet up with some of the people I met on my random 30th birthday party!

    1. AWESOME. That is one hell of a story Kevin – I’m glad that you took advantage of your layover. I couldn’t imagine turning down any opportunity to explore. 😀

      And how great is it that you made lifetime friends?

  9. Congrats on the WooThemes job! Chicago is a city that my travel bloggers friends have just raved about, and I’m raring to go there too, especially after seeing Toronto and Montreal here in Canada…!

  10. I would love to see Chicago some day. It’s so iconic to the USA.
    I feel as if it were dwarfed by New York, Los Angeles, perhaps even Washington. But I’d love to visit it…

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