Can you leave a Hibiscus plant outside for winter in the Chicago region?

For the typical hibiscus, no - it's a true tropical and will freeze. The Rose of Sharon is a common northern tree/shrub and should do well. There are also a couple of new hibiscus cultivars on the market that claim they will survive up to Zone 5 - it should tell you on the label if it's this kind of plant (I would recommend protecting it like you would a rose). If no label, then it's probably the tropical variety - and should be brought indoors for the winter.

Can you leave a Hibiscus plant outside for winter in the Chicago region?
Not the usual hibiscus. The frost will easily kill it. However there is an equivalent shrub, Rose of Sharon (Hibiscus syriacus), that can easily survive Northern winter like those in New England. Same flowers but woodier and very hardy.
Reply:It depends on the variety. I am in zone 5, and mine stays out, in the ground, all year. Check the plant label, or take a leaf to a garden center. NOT HOME DEPOT
Reply:No, tropicals won't survive your winter. Heat and humidity encourage bloom, cuttings will root in water. You can overwinter hibiscus inside.
Reply:NO!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!...
Reply:Faith, I live in Florida and have my whole lawn perimetered by hibiscus. They are a very hearty southern plant but I personally think the frost will kill the roots because the plants are not indiginous to the north. I think they will do fine indoors near the window to catch some sunlight then take them back outside in the late spring.