Galena & Northern Illinois
The highlight of this region is the hilly northwest, where cottonwood trees, grazing horses and scenic byways fill the pocket around Galena. En route is Union, where the Illinois Railway Museum sends trainspotters into fits of ecstasy with 200 acres of locomotives.
While it sometimes gets chided as a place for the 'newly wed and nearly dead,' thanks to all the tourist-oriented B&Bs, fudge and antique shops, there's no denying little Galena's beauty. It spreads across wooded hillsides near the Mississippi River, amid rolling, barn-dotted farmland.
A surprise awaits near Collinsville, 8 miles east of East St Louis: classified as a Unesco World Heritage site with the likes of Stonehenge and the Egyptian pyramids is Cahokia Mounds State Historic Site. Cahokia protects the remnants of North America's largest prehistoric city (20,000 people, with suburbs), dating from AD 1200.
Evanston & North Shore
Evanston, 14 miles north of the Loop and reached via the CTA Purple Line, combines sprawling old houses with a compact downtown. It's home to Northwestern University. Beyond are Chicago's northern lakeshore suburbs, which became popular with the wealthy in the late 19th century.