Route 66 begins in the middle of the Loop, a few steps from Lake Michigan, on a downtown street where a small brown sign marks the start of the road that once ran to Los Angeles. Chicago was the logical beginning. By 1926, when the highway was commissioned, the city was already the rail and trade hub of the Midwest, and farm families, migrants and travellers poured out of here along the road westward, the one that John Steinbeck later called the Mother Road.
The city itself rewards a day or two. The Great Fire of 1871 wiped out much of the centre, and the rebuilding turned Chicago into the birthplace of the skyscraper, so that walking or taking a river boat tour among the towers feels like looking at an open-air museum of architecture. The Art Institute, just by the start of Route 66, holds a world-class collection, and Millennium Park next door has the shining bean sculpture that everybody photographs. Lake Shore Drive curves along the water in a long arc with the skyline on one side and the lake on the other, and at dawn it is one of the best city rides in North America.
Eating is also an event. Deep-dish pizza is the famous dish, and the Chicago hot dog, topped with onions, relish, tomato, pickle, peppers and mustard but never ketchup, has strong defenders. Italian beef sandwiches, dripping in juices, are a more local pleasure.
As a place to start a ride, the downtown has some challenges. One-way streets, taxis, buses, bike lanes and trams crowd the roads, and parking is expensive, so you will want a plan for your bike overnight. Fuel stations are scarce in the very centre, so it makes sense to fill up on the way in or after leaving the city on the southwest side. Traffic eases a little after morning rush, and early on a Sunday the city is very quiet.
From here the old road follows a patchwork of alignments, from city streets to quiet county lanes, through suburbs toward Joliet and then into the farmland of central Illinois. Cornfields, grain elevators and small-town diners take over, and the pace and the sky both expand. Spring to autumn are the rideable seasons, with winter cold and ice making the plains dangerous.