Chicago, A Place to Call Home in Retirement?

I’ve often asked myself that very question, and I hear repeatedly from friends looking to leave Illinois for supposed greener pastures, hypothetically less crazy politics, and lower property taxes questioning the very same. But I think Illinois and Chicagoland, specifically, have some great reasons to live here in your later years.

Why Do You Have THAT Number?

I usually am asked why I still have a personal cell number that is a Colorado number, and it comes up that I moved in 2009 from the Denver area back to Chicagoland, where I had lived my whole life until 2001. Almost every time, the next question is, “Why did you move back here? Colorado is so beautiful.” And while that is undoubtedly true, Colorado’s “seasons” can’t compete with our four seasons. Our vibrant, beautiful green lawns, explosion of colors throughout the summer, lush swaying fields, and fantastic fall color display illustrate the variety we get from springtime to harvest. Snow and cold are predictable. We know we will have cold and snowy weather starting in late November, and we’ll be done by March. I like that seasonal certainty.

Not only that, but we have some sweet trail riding for being one of the flattest areas of one of the flattest states. Guys like me who like to shred mountain bike trails have no shortage of fun here. There’s also the beauty of countless county and state parks that offer fishing, camping, and hiking to places I bet you’d be surprised exist in the Chicagoland area. We have access to a network of casual biking and walking paths that can take you from Dekalb to St. Charles, Oswego to Carpentersville, and Aurora to Maywood. For some reason, though, Illinois has gotten a bad rap when it comes to the great outdoors. Being in retirement, get out there and explore these places, and appreciate the unexpected beauty of the Chicagoland area.

Home Base and a Jumping Off Point

If you read my July article about planning for extended travel, you know it’s one of my top enjoyments. What could be better than living in Chicago and it being the jumping-off point for wherever you want to go? Domestically, you’re about halfway to any coast and have a wide array of international destinations you can reach seamlessly. Being in a well-connected larger city gives you more options and reasonable airfare to get there. I once took a direct flight from Chicago to New Delhi, which was unavailable when I lived near Denver. I can tell you that it’s MUCH nicer to take one 16hr flight than to fly 8 hours to a connecting city in Europe, wait for hours for a connection as a dead tired parent with a crying one-year-old, and then grab another 8-hour flight to your final destination. My wife Tanya and I have decided that Illinois will be our home base to launch out from for our travel, family activity, and service.

Second to None City

Let’s not miss the greatness of staying in Chicago to enjoy the restaurant, sports, music, and theater scene. Chicago and the surrounding areas are regarded by many as a premier culinary delight. With such diverse ethnic groups in and around the area, there’s no shortage of tastes to tantalize your tastebuds. Looking at the show and theater scene, we have tons of options, like comedy with Second City and long-running Broadway shows like Hamilton. Finally, when it comes to music, we have chilled-out music scenes like Ravinia and suburban downtown city parks to places where mash pits are the norm, like Grant Park for Lollapalooza. The point is that the possibilities are abundant, with options to fit any want. Over and over, Chicago is ranked at the top of the list for restaurants, sports, stage performances, and music.

Illinois Taxes, What a Retirement Relief

It doesn’t matter where you live; the federal government will always treat your income the same whether you live in Illinois, Texas, Georgia, Tennessee, Arizona, or Florida. However, states have varying treatment on retirement income, that is, income arising from sources other than taxable investment accounts, interest-bearing bank accounts, and earned income from a job. Illinois is one of 13 states that doesn’t tax retirement income like distributions from a 401k or IRA. Nor does Illinois tax monthly pension payments or Social Security income. These streams of cash are subtracted from your federal adjusted gross income before the Illinois Department of Revenue assesses our flat 4.95% tax rate. If your only income derives from these sources, your income tax burden is precisely $0. That means the more you can sock away in tax-advantaged investment accounts, the less you will pay down the road as you live out your Illinois days. That’s an unexpected advantage that you may not have been aware of.

Your Partner in Planning

At The Dala Group, we support you in pursuing wherever and whatever you are most passionate about in retirement. We can guide you to position yourself so that you can live with purpose and enjoy all that the Chicagoland area offers. Click here to schedule an appointment.

https://www.timeout.com/chicago/things-to-do/chicago-bike-trails

https://www.timeout.com/chicago/things-to-do/the-best-places-for-hiking-near-chicago

https://www.timeout.com/chicago/restaurants/best-chicago-restaurants-our-picks-for-every-cuisine