Skinnyski.com gives trail conditions, race & lodging information.
Friends of Lapham Peak provides a trail report of this popular, nearby skiing destination.
Stokely Creek Lodge, Sault Ste. Marie, ON, is a world-class destination for cross-country skiing and snowshoeing (closed in 2020-2012 due to covid).
Maplelag Resort, MN, has proven popular with NNSC.
Minocqua Winter Park is an evergreen favorite and the closest natural setting to Chicago (about 5 hours drive).
South Kettle Moraine State Forest is probably the nearest significant trail system near Chicago (1.5 hours).
XCSkiResorts.com is a useful site for planning longer trips in the U.S. It lists all of the major sites including Maplelag, MN; Minocqua Winter Park, WI; and other U.S. locations.
XC Ski Headquarters in Roscommon, MI is the best! Call Bob and he'll give you advice and options.
(Good options also exist at Minocqua Winter Park and ABR if you join one of those trips.)