Where Should I Retire?: I’ll have $10,000 a month to spend and prefer a city with beautiful outdoors, warm weather and lots of culture — so where should I retire? No Comments Uncategorized And she wants it to be cheaper than Chicago. And she wants it to be cheaper than Chicago. Share this:Click to share on Twitter (Opens in new window)Click to share on Facebook (Opens in new window)Click to print (Opens in new window)Click to share on LinkedIn (Opens in new window)Click to share on Tumblr (Opens in new window)Click to share on Reddit (Opens in new window)Click to share on Pinterest (Opens in new window)Click to share on WhatsApp (Opens in new window)