The roaster is quite cool.
You might have added Burt Gummer from the Tremors series, a redneck with a soft spot for anything that shoots more bullets in a fraction a second than there are teeth in a toddler's mouth. Comes with tons of experience with explosives too, while fighting deadly predators moving around underground.
He's used to keep an eye on the environment.
Dutch would be a good addition too. The guy survived against one of the deadliest and smartest hunters from outer space, outwitted said fella and survived a nearby super blast.
From the original cast, they all look powerful, and the advantage goes to those who know the cities. Some of them clearly come from a fantasy setting and might face difficulties with modern structures and mechanisms, and could find themselves trapped in a rather stupid way, although some of them might also be able to smash their way through some of those obstacles.
Still, being able to operate a radio or a car for example would be good.
Also, ranged weapons are better and people used to modern weapons will fare better in Chicago.
Escaping by boat might be the simplest course of action. The marina are right in the middle of the city.