PHOTO IS ERA APPROPRIATE ONLY!!
I didn't check the appliances! I didn't check the appliances!
It brought to mind a client's statement that I quote over and over and over again: "If you don't keep your house up, it becomes an overwhelming proposition." If you haven't made any changes since the 80's or 90's (or especially the 70's) it's probably time! If you have classic and/or antique furniture, lighting and rugs, good hardwood/stone floors, shutters, wood blinds or simple drapes on your windows, you might get a pass (maybe partial). Good wood kitchen cabinets, stone or some kind of resin countertops, little or no shiny brass (other than maybe door hardware) and well-selected art and accessories can also keep your home from being OLD.
But, if you're surrounded with radius corners on laminate furniture, fake hand-painted fabrics, mauve (or peach) and gray color scheme, tile (esp. 8x8) with wide grout lines (unless it's natural clay tile), faux Art Deco, short vertical or micro mini blinds (esp. silver), VERY dark red, green or lots and lots of black-brown, foil or complicated textured wallpapers it's time to update. Also in that list: colored appliances, Lucite and metal sconces (although the furniture is good), upholstered "bun feet", or bleached oak floors.
If you are buying new (or new for you) items, replace dated pieces with classical styles or vintage/antiques, which are past being a "rage". That does NOT mean traditional or old-fashioned!! If you want to re-decorate as a hobby and to continue changing things every couple of years, spend accordingly. Most of us don't have time, access, money or interest to do that. Put together creative color combinations (again, NOT what everyone else has) and you will be set for a much longer time. A design theory lesson is that you can combine any colors together in the proper amounts: Color 101.
You can update with big items like new furniture, an all-new kitchen or all new floors, or you can update PLENTY with paint, new window coverings, counter tops, backsplash tile, and/or accessories. Find colors to repaint which work with your older furnishings (incl. cabinets, etc). Rip out old wall to wall carpet and put in a pre-finished floor (or re-carpet). Switch things around: dump the peach abstract prints with the matching ceramics. Go to the Art Center in Highland Park and donate to their "Recycled Art Fair" in July, or give the old stuff to Goodwill and find something new (or new for you) to change things up. I have never seen so much 80's art as last summer in HP. -- Maybe research (at least on eBay) to check if the art has enough value for you to sell it and get cash instead.
Limit the "do it yourself" to what you CAN do; what's listed above could be more than you're able to do alone. It could be time for Professional help (Design kind).
If you're up for something different & have fun, Chicago is full of art fairs, flea markets, garage and rummage sales all summer. And keep in mind that many of the established art fairs like 57th Street this coming weekend and Old Town, have adjacent fairs that could be more affordable. Toss out the old, freshen up, & perhaps don't start all over - yet.