Retirement: Why to STAY in Chicagoland

Jonathan Henkels |

Many people consider moving when retiring.

 If you live Chicago or its suburbs, it may be a good idea to stay put.


I have had many conversations with friends and family over the years where the topic of leaving Chicago and the suburbs comes up.  I’m sure that many of you have had the same idea if you live here; some of you may have even left the area.  A lot of my friends are entertaining the idea that life would be better somewhere else and are considering retiring elsewhere.

Of course every situation is different, but there are also a number of reasons people live in Chicago in retirement.  As time as gone on, despite all its faults, there are many things about where I’ve grown up that are very special.  Here are a few of the best reasons to stay in Chicago once retired:

O’Hare and Midway Airports

Travel is often a big part of the retirement plan for many people.  If that is a goal for you, one thing that is overlooked is how much work it takes to get from point A to point B.  I’ve talked with enough people to know that eventually the biggest reason they stop traveling is because the journey there becomes too difficult. 

I think we often take for granted how many direct flights leave Chicago for cities all over the country and world.  Just this last summer, the flight to Munich from Chicago allowed my family to enjoy the city even more because we didn’t have to wait in airports for layovers.  If you plan to travel, Chicago is a great place to begin your journeys.  It also makes coming to visit us easier for family and friends! 

World Class Museums, Entertainment and Diverse City Neighborhoods

Now that you have more recreational time to build into your schedule, Chicago has some of the best museum and architecture scenes on the entire planet.  Special exhibits come to the Art Institute all the time; in fact I’ve been able to view many exhibits in the summer that are normally available only in Europe.  The architecture of our city is world renown and you can choose from multiple tour venues.  The Shedd AquariumField Museum, and Adler Planetarium are even more great ways to spend a day with your family and friends.  They are also very accessible and close to one another to make it less difficult to visit more than one during a single day trip.

In addition, there are wonderful hotels with amazing views of Lake Michigan, a free public zoo in Lincoln Park and of course, another Chicago landmark – Brookfield Zoo, as well as lots of great shopping opportunities in The Loop showcasing special holiday markets such as the Christkindlmarkt in December held in Daley Plaza. 

All of the Broadway shows eventually play through Chicago, so opportunities to see amazing theater remain available throughout the year in the bustling Downtown Theater District, home to the Cadillac Palace Theatre, Auditorium Theatre and Broadway Playhouse. 

Much of the Lake Michigan lakefront is open to the public, so a day at the beach doesn’t mean taking an airplane ride to a tropical venue.  Consider one of the many boat tours along the Lake if you feel like playing on the water rather than in it.

Chicago also has a rich cultural history related to the various ethnic groups that have come to America.  In particular, there are strong associations of Irish, Polish, and German descendants.  They all have special cultural events to attend where one can learn more about the history of the city. 


The Chicagoland area attracts some of the best health professionals from all over the country.  There are numerous world class hospitals and specialists in the city and suburbs.  Medical issues can be very complex and Chicago offers top-level specialists who practice at NorthwesternLoyolaUniversity of ChicagoLutheran GeneralRush, and other high ranking medical facilities.  Many of the best medical students take up residency and stay in Chicago, helping to make it one of our nation’s best metropolitan areas for medical care.

Tax Free Pension and IRA Withdrawals

It is great to have the advantage of saving money on the tax advantaged treatment of retirement accounts, but governments eventually want to be paid.  The good news about Illinois is that it is one of the few states that doesn’t tax you on the back end.  As of 2019, Illinois does not tax pension distributions and withdrawals from IRA accounts, as well as other “qualified” retirement plans (403(b), 401(k), 457, etc.).  With a state income tax rate of 4.95%, this is a significant advantage when considering staying put. 

So when considering leaving Chicago, keep in mind some of the factors that actually may make it the best place for you to live during the retirement phase of your life.  Not only are you closer to us here at Phase 3, but there are many wonderful things within our city and metropolitan area to experience and enjoy.