Fly-drive Chicago

Chicago was the starting point to one of the world’s most famous roads – Route 66. It ran all the way up to Los Angeles. Decommissioned in 1987, the road no longer appears on maps, but you can still drive along parts of this historic road on your way West. See iconic neon signs and visit drive-in cinemas and restaurants along the way.

Spend 5 days crossing several states on your way to the Smokey Mountains. Drive to the plantations in Nashville and Chattanooga, and then admire the scenery of Cherohala Skyway en route to North Carolina. This part of the journey should take approx. 3 days. Take a detour via Tennessee, to see the other side of the mountains, before making the trip slowly back to Chicago.

Follow Lake Michigan through Michigan state, stopping off in Onekama. Stay the night at Portage Point Inn, a classic hotel facing the lake. Drive 8 miles north of Onekama to Arcadia, for great dining, golf, sand dunes and scenic views. From here drive to Leland and stop at this historic ‘fish town’, surrounded by two lakes, perfect for a spot of canoeing. Then onto Mackinaw, to see the Mackinaw Bridge, before heading down the Garden Peninsula to Manistique and the restored mining town of Fayette, near the tip of the peninsula.