Can a hibiscus plant survive a Chicago winter?

Yes, but be sure you have a hardy variety. Tropical varieties will not tolerate frost, although people do grow them in northern climes. You just have to keep them in pots and bring them inside before the first frost. A hibiscus with glossy, deep green leaves and red, pink, orange, or yellow, double or single flowers is probably a tropical variety. A perennial, hardy hibiscus will have dull, medium-green, heart-shaped leaves; dinner plate-size white, pink, or red flowers; and huge, bomb-shaped buds. A hardy hibiscus needs very little care over the winter and is hardy to about Zone 5 with no protection. Growing a hibiscus inside during the winter may require artificial light. No matter what, you can’t expect as much lush growth and bloom from a hardy variety as you see in the tropics.