Many thanks to ItsFilmedThere for identifying these locations. Check out this and many other Chicago-based movies over there.
Arriving in town - Woodstock Square, Woodstock, Illinois
Pennsylvania Hotel - Woodstock Opera House, 121 Van Buren Street, Woodstock, Illinois
The bed-and-breakfast where Phil Connors (Bill Murray) stays - 344 Fremont Street, Woodstock, Illinois
Ned's corner - Cass Street at Benton Street, Woodstock, Illinois
Tip Top Cafe - ABC Restaurant, 108 Cass Street, Woodstock, Illinois
The Groundhog Day celebration - Woodstock Square, Woodstock, Illinois
Alpine Theater - Woodstock Theater, 209 Main Street, Woodstock, Illinois
Your photos look better than the film scenes.
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