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Whether you want to downsize your current home for a more carefree lifestyle or you’re ready for a fresh start in one of the most exciting cities in the country, retiring in Illinois with Upside could be exactly what you’re looking for. From world-class museums, performance venues, and professional sports teams to walkable neighborhoods brimming with unique dining and shopping experiences, life in the Windy City will blow you away. Head north on Lakeshore Drive and admire an iconic skyline punctuated by stunning skyscrapers and flanked with panoramic views of Lake Michigan. Here, every sidestreet is an opportunity to find your next favorite “thing,” whether that’s a new deep dish pizza joint, trendy record shop, or a secret, prohibition-themed cocktail bar.
Retiring in Illinois, specifically in Chicago and the surrounding suburbs, is the perfect choice for people who want convenient access to top-tier cultural landmarks, entertainment, dining, and shopping in a city that is relatively easy to navigate on foot, by car, or using readily available, affordable public transportation. With dozens of distinct neighborhoods – each with their own unique charms – you’ll have fun getting to know them all.
Of course, you’ll also love coming back home to your Upside apartment. With numerous apartments in Chicago and the nearby communities, finding the right home for your way of life has never been easier. That’s because Upside apartments are hand-picked from some of the best communities and buildings around. And that’s just one benefit of retiring in Illinois as an Upside member!
Can’t get enough of big-city living? We’ve got apartments for you. Rather head to the suburbs? Upside has many apartments for you to choose from as you embrace the entirety of the Windy City. But make no mistake – Upside is not a typical retirement community in Illinois. Upside is for active adults who want more time to do what they love or to discover new experiences without compromising on anything.
Most of all, retiring in Illinois as an Upside member means you get the “real” Chicagoland experience – not a restricted daily schedule. With your own personal Upside Manager to help connect you to the activities you love, it’s easy to make every day your own. All without hidden fees or surprises. With us, retiring in Illinois is all Upside.
55+ communities in Illinois are more than great places to retire when they’re Upside communities. That’s because all of our retirement communities in Chicago are structured to maximize the inherent benefits of life in the Windy City while making it easy for you to enjoy a maintenance-free lifestyle with more time for what really matters. Factor in Chicago’s world-class entertainment attractions and you’ll find yourself with a renewed sense of possibility. Browse our selection of 55+ communities near Chicago, and elevate your quality of life with our streamlined, all-inclusive apartment experience.