Our Chicago Weekend

Despite being only 100 bucks a plane ticket and Groupon hotel deals every week, Becky and I had yet to take a trip to Chicago. When my job took me to Chicago for the Business Marketers Association Conference June 1-3, we decided to stay a bit longer and have a nice weekend in a new city. Becky had enough miles to get tickets for only 11 bucks, so it was a bit of a no brainer.

Throughout the spring, we socked away money for the trip and payed ahead for things when we could so that we would be able to be budget conscious and still be able to relax and not worry about money the whole time.

We spent the three conference days at the Hilton Chicago, which is a stately building from 1927 right along the park in “the Loop.” The hotel was beautiful, though severely understaffed. Two notes – it took as long to get to the hotel from the airport as it did to fly to Chicago. It also took almost as long to check in at the Hilton. One guy became my hero when he signed up for Hilton rewards while waiting in line so he could move over to the fast line.

This artwork was in our room and I had to wonder, why is there a picture of a bear vomiting glitter on a wall?


Several days later, we solved that mystery:


The hotel is also seen in a ton of TV and movies, including the helipad for ER and the big conference scene at the end of The Fugitive: “You switched the samples!”

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Well done, Hilton!
Well done, Hilton!



You Switched the Samples!
You Switched the Samples!

I spent the days learning about business marketing and god knows what. Becky relaxed. At night, we met up and went to lovely eateries she had found. Tapas at Buleria one night, Italian at Volere the next. By Friday, my head full of marketing, especially the contradiction that comes up all the time at these conferences (be innovative, but prove your worth with ROI (Return on investment), but you can’t be innovative unless you can show ROI — basically, be innovative, but make sure that risk pays off because risky things always work).

Buleria for Tapas!
Buleria for Tapas!

Friday, our real Chicago adventure began, starting at Millennium park.

Obligatory Cloud Gate pics!

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Yes, that's a guy in a duck costume walking around in ungodly heat
Yes, that’s a guy in a duck costume walking around in ungodly heat

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We headed to our lodging for the weekend, a B&B in Boystown, a gay neighborhood in Chicago. It was a lovely neighborhood with helpful places nearby for food and other stuff. Our room was pretty small, but we made it work, any warmer and we may not have. The B&B people, however, were congenitally grumpy. Every interaction with them, even when I was trying to help out, I seemed to be doing something wrong, even when I was following the signage posted throughout the house, I was doing it wrong. Like when I left my plate in the sink as the sign said, the guy snipped at me to just put it in the dishwasher, which the sign said to NOT do.


Example conversation I had:

Me: Hey, are you the guy to talk to about cleaning?

Him: Why what’s wrong with your room?

Me: Oh, nothing, it’s great. Just wanted to say we don’t need any cleaning today…

Him: Then put up the do not disturb sign on the door!

Me: Sure. But, we will need a towel.

Him: Then don’t put up the do not disturb sign on the door!

Me: Ok, thanks!


After some take out barbecue, we went to Second City, a decades-long dream of mine. It’s an institution that started the careers of many of your favorite comedian actors. The show we saw Fool me Twice, Déjà vu – was astoundingly funny and witty. After the intermission, they re-did a lot of the same sketches, but this time through different points of view, different characters, extended endings and more – very meta. We’re keeping the program so five years from now we can see where they all are.



Saturday we headed to the Institute of Art Chicago. I was able to show Becky why Van Gogh is so much cooler than you realize when you see his stuff in person. I love the three-dimensionality he puts into the paintings –thick smears of paint rise off the canvas like a 3 dimensional relief map. It’s something that can’t be printed. I also got to make this vine:


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Saturday night I got takeout from the Dive Bar next door, that’s their name, not a description. While waiting for my order, I got a Blue Marlin, that comes like this.



Sunday we went to Wrigley Field to watch the Cubs and Diamondbacks play. We weren’t there for the team so much as the field, like a baseball mecca that demands pilgrimage. No elevators in this old park, so getting to our seats was a hell of a trek up a ton of ramps, and food stands in the upper decks are scarce. They even ran out of hot dogs, chicken and fries before the second inning. On top of that the weird seat numbering system meant our seats were together even though we were in different sections and there were 100 numbers between Becky’s seat and mine.

None of that mattered though. It was a gorgeous day for baseball. We had a lovely view of the park and surrounding buildings that have seats on their roofs to watch the game from outside the park. Found out they are called “Wrigley Rooftops.”

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We left the game early and took a nice relaxing trip down around the loop on the el for an hour before heading home.



I ordered a deep dish and fries. When it arrived, I opened it and it looked like an ordinary pizza. It turned out it was, but we were too hungry to care. Half an hour later the phone rings, it’s the B&B guy.

Him: The pizza guy is here.

Me: I already got my order 30 minutes ago.

Him: Well he’s here!

Me: Ok, I’ll be up.

So he gave me the right order and we were able to shove about a bite a piece into our already full gullets before calling it. We’ll have to have the full deep dish experience another day.

All in all, it was a nice trip. Not our best trip. I’d like to return to try again sometime, but not until after a long list of other destinations has been marked off. One thing Chicago has going for it, though, is cheap as hell airfare. Just be sure to pick a week that the hotels are not packed to the brim.

Oh, they also have Dunkin Donuts, a love of Becky’s from her Boston days that we don’t get to partake of in MN


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