When it comes to prime locations for retiring travel-buffs, Chicago arguably tops the list in the U.S. Its nickname, the "Crossroads of America," hints at its excellent connectivity. The city is home to two thriving international airports and serves as a crucial Amtrak hub, making it the ideal location for retirees itching to jet off or embark on a train adventure. Additionally, the city and its surrounding regions, collectively tagged as "Chicagoland," offer an array of local attractions for those preferring to explore closer to home, making it a paradise for those with a love of travel.
O’Hare International Airport, being one of the world's busiest airports and located just 18 miles from downtown Chicago, is serviced by around 50 international and domestic carriers. Meanwhile, Midway International Airport, although smaller and older, is a crucial hub for domestic travel.
Besides benefiting from these significant air transportation resources, train enthusiasts can enjoy Amtrak's services from Chicago’s Union Station, with a variety of routes spanning the U.S. There are also plans to establish an Amtrak route stretching from Chicago to Windsor, Ontario, which will link to the Canadian railway system VIA Rail Canada, set to launch in 2027.
Although not known as a primary destination for cruise ships, Chicago does offer a selection of Great Lakes cruises, given its position as a Lake Michigan port city.
As for local living expenses, the cost of living in Chicago is reportedly 14% above the national average, primarily due to housing costs. The retirement income, which typically includes Social Security, pension benefits, and yields from retirement accounts, generally enjoys exemptions from state tax, while the city imposes no income tax of its own. This feature would be particularly beneficial for high-income retirees.
In terms of attractions, Chicago is bursting with world-class theaters, music, art museums, parks, restaurants, and unique ethnic communities. The city also hosts well-known universities such as the University of Chicago and Northwestern.
Sporting enthusiasts can enjoy warm- and cold-weather sports in Chicago's parks, while sports fans have numerous professional teams to choose from. For healthcare needs, retirees will find numerous top-tier medical facilities available.
However, despite its many attractions, Chicago isn't all sunshines and rainbows. It grapples with issues pertaining to crime, traffic, and other municipal problems. Plus, its contrasting seasons - humid summers and snowy winters - may not suit everyone's taste. Therefore, retirees pondering a move to the Windy City should ideally experience it in all seasons, possibly renting for a year or two before purchasing a house. Despite winter's harshness, many retirees may find that Chicago perfectly matches their retirement dreams.