Chicago, Illinois is a great city to visit. And for some reason unbeknownst to me, most people I know visit this fair city in the winter. Don’t get me wrong, there is plenty to do, see – and eat – in Chicago at any time, including the winter, but summer for me is the best time to be here in the city along Lake Michigan.

That being said, people come, and you may well be one of them. This is why I am sharing these tips for you, things to do or be aware of specifically when you are here in the winter months, as you won’t want to waste any more time outside than you need to.

#1 – Get a Ventra transit card ahead of time or when you first get to Chicago – In 2014 the Chicago Transit Authority (also known as the CTA and the “El”) outsourced its fare system which calls it Ventra. The Ventra card is technically a MasterCard debit card with the paywave feature, and can be used as both a transit card or as a standard debit card (but you don’t have to, or most likely won’t want to). You can buy a Ventra card online or at retailers in the city. If you register it online, you will get the US$5 you paid for the card as transit value on the card. You can also set it to autoreplenish from a credit card so you don’t have to spend time in the cold reloading the card at a kiosk.

#2 – Use ParkChicago for mobile on-street parking payment – Chicago also outsourced its parking meters and one benefit from it is the ParkChicago mobile payment system, where you can pay for your parking using a mobile app, mobile Web site on your device’s browser or even pay by text message. It requires a registration and the system works very well.

#3 – Familarize yourself with the Pedway – Below the streets of Chicago is the Pedway, a system of mostly interconnected tunnels in and between city buildings downtown in the Loop. Note you can’t get everywhere through the tunnels and walkways, but it is convenient to get to some places, like public transit stations, without going outside.

#4 – Look into joining a museum you are visiting to save money – Chicago has some great museums, and the larger ones charge admission. If you are bringing the entire family, the cost can add up. When you get to your destination museum or aquarium or planetarium, look at the cost of joining. Depending on how many people are in your party and if you are looking to see special exhibits for added cost, it may be cheaper to become a member and get free admission. If you think you may return to the place, membership is a no-brainer.

#5 – Bring your own ice skates to Millennium Park and Maggie Daley Park – Chicago has 2 skating areas downtown, the McCormick Tribune Rink at Millennium Park and the skating ribbon in the newly-opened Maggie Daley Park (formally called Daley Bicentennial Plaza before the park was literally dug up as it’s on top of a parking garage, and you can read more about that here). Where skating at both places is free, there is a fee to rent skates. That in itself is not the issue; it is the logistics of renting them, which usually requires a long, long wait in the cold. This is why I recommend bringing your own skates to the rink, then you can lace up and hit the ice. If you don’t have your own skates, take a short train ride to either Sports Authority in River North or Dick’s in the South Loop and buy a pair – the time saved will be more than worth it.

#6 – See a show – Whether it’s walking or waiting, the cold can get to you. Fortunately just about every night of the week there is quality entertainment at the over 100 theatres in the city. From plays to sketch comedy to improv, Chicago has plenty to offer for all tastes and genres. You can learn more on the theatres at the League of Chicago Theatres and get half-price tickets to shows at HotTix. On Monday nights, you must see That’s Weird Grandma by Barrel of Monkeys!

#7 – The sales tax in Chicago is 9.25% – Though you have no control over the sales tax here, it is something to consider, as at is rate it can add up quickly. Not to mention taxes on hotels, meals, parking and even bottled water. There is a tax on candy too, but it is cheaper for Tix and KitKat, as both contain biscuits made of flour, and since grains are grown in Illinois, it has a lower tax. I am not joking on this!

Enjoy your trip to Chicago, and especially the food. If you like it in the winter, come back in the summer as it’s even better.

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This is from The Hot Iron, a journal on business and technology by Mike Maddaloni.

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I was recently invited to write a guest post on the blog for CorporateStays.com, a service which matches luxury accommodations for travelers in select cities in the world like Montreal, Miami and Panama City. Digging into my experience with travel, I decided to write about tips for traveling in the winter months. My post, Travel Tips for Travelling to a Wintery Destination, is now live.

Where my typical writing is about business and technology, I file this under the “occasional diversion” I refer to in the description of The Hot Iron. The more I write, the more these come to mind, and the more these may be available to read by you and others.

Thanks to my good friend CT Moore and the staff at CorporateStays.com for the opportunity to write this.

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This is from The Hot Iron, a journal on business and technology by Mike Maddaloni.

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Happy 2015! As today, the second day of January, officially marks the first business day of the year, and by now most have recovered from the merriment of New Year’s Eve, I would like to wish you all a great new year.

Where rolling to a new calendar also comes with resolutions, mine is simply to mix it up in 2015. I started the new year off much differently than I did in past years: sans kids, just me and my lovely wife at a Spanish restaurant, where just about every year that I can remember has involved Chinese food (a Boston tradition) and the past several years have been with our kids, even if they were sleeping in the next room. This was a fun change, and a great way to ring in 2015.

So in mixing it up in 2015, I am not looking to make major strategy changes, but smaller, incremental changes that I see as adding up to something bigger and better. Maybe I take a different route to go someplace, or a different approach to reaching out to someone, or simply wear a different color socks on occasion – I am hoping to stop and think when I get into doing something routine or that comes too natural to me, and think how to change it in some way.

The Hot Iron at 8

December 30 marks the official anniversary of the launch of this little blog which is now 8 years old. It’s almost wild to think I have been at this, at varying degrees, this long. Writing is something I have enjoyed more and more over time, and it has been both a creative outlet as well as a way to vent some of my frustrations over business and technology – the overarching theme of this repository. Whether this is your first time reading or you are a long time subscriber – thank you!

I have written an anniversary post of mixed sorts over the years, and if you’re so inclined you can read them for the following anniversaries of The Hot Iron: first, second, third, fourth, fifth, sixth and seventh.

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This is from The Hot Iron, a journal on business and technology by Mike Maddaloni.

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To all of my family, friends and readers who celebrate the holiday, Merry Christmas! To everyone else, have a great Thursday!

As the origin of Christmas is the celebration of the birth of Christ, I share the above picture of my nativity scene. This was a gift from my Mom many years ago, as she gave myself and my sister identical nativities. I am proud to share it with my little ones.

So that is the traditional celebration of Christmas. Now for the non-traditional way.

I ran across this video the other day and I was speechless. It is a Star Wars Christmas special that aired on TV back in 1978. You can read the full story about it here if you’d like, or you can just view the show embedded below or by following this link to Vimeo.

Though I was a young lad back in 1978, I don’t remember this show that aired only once. After watching it – ok, even reading the premise of it – that is probably a good thing. If you are a die-hard Star Wars fan or just a casual one, you will find this amusing to say the least.

If you like it, then consider it my gift to you. If you don’t, then we can just forget about it.

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This is from The Hot Iron, a journal on business and technology by Mike Maddaloni.

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After Thanksgiving Thursday, Black Friday and Cyber Monday, if you have anything left, I welcome you to join me and support a great organization, Barrel of Monkeys, for Giving Tuesday.

Though I don’t know the story about how Giving Tuesday came to be, I know well the story of Barrel of Monkeys – what they do, how they do it, and the impact they have made on school kids in Chicago.

In short, Barrel of Monkeys teaches elementary school kids creative writing in several Chicago Public Schools and an after-school program. They learn how to create a story from beginning to end, journaling them in their notebooks. These stories are then adapted into sketch comedy by the Barrel of Monkeys company members and performed for the students in their schools. So not only do they learn how to write creatively, they also see their work come to life!

But that’s not where it ends – every week there is a performance by the Barrel of Monkeys company members, where several of these sketches are performed to audiences live. Each sketch is introduced and the student author is acknowledged, and the program given to each audience member has what the students actually wrote – sometimes it’s just a sentence, other times it’s several paragraphs and everywhere in between. The company members donate their time to perform, and all money raised goes back into the overall program.

The preceding gives only a synopsis of the great work Barrel of Monkeys does – you can read more on their Web site @ barrelofmonkeys.org or see for yourself their programs and some of their sketch comedy performances on their YouTube channel.

Below is a funny video promoting Giving Tuesday and Barrel of Monkeys, performed by Barrel of Monkeys company members and staff Elizabeth and Joseph – watch the embedded video below or you can view it directly on their YouTube channel.

Thank you for your support! And why would I be thanking you and promoting Barrel of Monkeys? I am proud a member of their Board of Directors.

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This is from The Hot Iron, a journal on business and technology by Mike Maddaloni.

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