Is buying a 2-bed high-rise condo in downtown Chicago (~$4.5k–$5k all-in monthly) smarter than renting for 4-5+ years?
Hey everyone,
I’m trying to figure out whether buying makes sense right now or if I should just keep renting. Would really appreciate any thoughts - I’ll be in Chicago with my company for at least 4-5 years, maybe longer, and I’m weighing the pros/cons of pulling the trigger on a 2-bedroom condo with a total monthly cost around $4k–$5k all-in (mortgage + taxes + HOA). I wish a normal mortgage was $3500 or less but welcome to Chicago taxes and hoa as you already know!
The idea would be to live in it for the next several years and then rent it out when I eventually move. Rents for nice 2-beds downtown are already $4k–$5.5k+ and keep going up, so I’m wondering if buying could help lock in costs and build some equity.
Preferred areas: River North, Streeterville, Gold Coast, Old Town — maybe Wicker Park or Lincoln Park if the numbers work.
I’m currently in a 1-bed near the river (rent was $2600 years ago and now $3200…) and would really like a decently high floor with a good view, balcony, and nice windows if possible. I know that pushes the price up and might not be the absolute best investment move (a duplex or something with rental upside could be smarter), but I’m in sales with a busy schedule and don’t have time for big renovations. Want to be downtown near my office/train and looking for move-in ready or close to it.
Chicago’s high taxes, HOA fees, and special assessments are my main worry. Does this overall strategy make sense for someone in my spot? Is buying better than renting long-term, especially with the plan to rent it out later?
Would love any recent experiences with high-rise condos in these neighborhoods, and any strong opinions on how the value will grow over time in say streeterville vs wicker.
What are the biggest things to watch out for (assessments, tenant laws, condo boards, resale, rental market, etc.)?
Any thoughts or data points would be really helpful — thanks in advance!