Expat Tales: Living the retirement dream in sports-mad, cycle-friendly Chicago

Free summer concerts, a stellar sports scene and cheaper gas and groceries help explain why former Aucklander Hamish Redmond has stayed in Chicago 25 years longer than he planned to.

I owned a software company in Auckland and business from the US was steadily increasing. In 1995/1996, we sold the business to a Chicago-based software company and part of the deal was that I come and work for them for at least two years in Chicago. Some 27 years later, I am still here!

I had spent two years living in Canada in the 1980s, so I was somewhat familiar with the culture. But it turns out there are substantial differences between Canada and the US, so settling in took a while. A lot of people asked whether I thought my New Zealand accent was an advantage or disadvantage in doing business and living in general. My opinion is, on the whole, a slight disadvantage, particularly with a first name of Hamish, which many people here have a real difficultly with. However, I can say that I love the people and city of Chicago and all it has to offer.

I was a software engineer in the Equity Option Trading markets, but retired at the end of 2022 and only work part-time now. I worked on and around the trading floor of the Chicago Board of Options Exchange (CBOE) for around 20 years.

Chicago has all the advantages of being a very large city. Everything you need or could want is readily available. Chicago is also a great sports city and has several iconic sporting franchises in the Cubs, Blackhawks, White Sox, and Bears football team.

It is also a very flat city and has great bike riding facilities, parks and beaches along Lake Michigan.

Chicago, somewhat unfairly, has a reputation for being one of the most violent cities in the US. In all the years we have lived in the city, we have never had any issues. However, street crime, car jackings and muggings – particularly late at night – are still a problem. You just have to be careful and aware of your surroundings.

We have not been to New Zealand since 2017, but based on that visit I would suggest it is cheaper – particularly for groceries, gas, and consumer goods. In the US, you must provide your own medical insurance and, depending on the size of the family, this can be quite expensive.

Rents and property prices are probably comparable, however property taxes (what you would call rates) are considerably more expensive here than what I remember in New Zealand.

From watching the Chicago Blackhawks win three Stanley Cups and the Chicago Cubs win their first World series in 108 years in 2016, we always find plenty to do.

Now that I am retired, we spend a lot of time enjoying what the city has to offer, including regular sporting events, bike riding and activities at the gym. Last year, we purchased two ebikes, which really make cycling an easy and relaxing experience.

If there’s one Chicago food that’s the best known, it’s Lou Malnati’s deep-dish pizza. Composed of a thick crust, zesty tomato sauce, personalised toppings and a behemoth layer of cheese, the deep-dish dares to be different. This is followed by Portillo’s Chicago-style hot dog and the Italian beef sandwich.

I do enjoy deep-dish pizza on occasion, am always ready for a Portillo’s hot dog, but am not a fan of Chicago-style Italian beef.

The city is well covered by the Chicago Transit Authority – both in the elevated trains (the ‘El’) and buses. Chicago is consistently ranked as the most congested city in the US, so unless you really need a car, stick with the El, bus, yellow cabs or Ubers – all of which are plentiful.

Chicago has a vibrant nightlife with many fabulous restaurants.The River North area has a host of nightclubs, as well as blues bars such as Buddy Guys and Kingston Mines, where you can hear some great blues music, which Chicago is famous for. Every year there are many famous musicians who put on concerts in one of the stadiums and, in the last few years, we have had concerts by Bruce Springsteen, Taylor Swift, U2, and Chris Stapleton – just to mention a few.

Summer is a great time to visit. You can take in a baseball game and hang out at the beach. Chicago has over 26 miles of scenic lakefront, which includes numerous public parks and gardens, an 18-mile trail, and more than two dozen free beaches that open to the public every summer in

.Over summer, every Wednesday, Friday, and Saturday there is a free music festival at Millennium Park, where you can sit on the lawn and listen to wonderful concerts.

A decent mince and cheese hot pie. There is an Aussie pie shop here, but they are just not the same. New Zealand dairy products, although Costco here now sells New Zealand butter, so there is some relief. Once one of the major food stores here was advertising New Zealand cheese, however it was accompanied by the Australian flag! I did point out to the store staff, the error of their ways.

Also, New Zealand beaches – although they have wonderful beaches here along Lake Michigan, it is just not the same as swimming in the South Pacific.