Cicero on Ogden Avenue heading out of Chicago is an industrial area with lots of hospitals followed by deteriorating neighborhoods. It's not particularly scenic, but the traveling is easy for leaving a major city. There are a few Route 66 landmarks along the way, including the Castle Carwash, Henry's Drive In with its giant hot dog sign and Cyndy Lyn's Motel and Suites.
Henry's opened in 1946 when Bill Henry, who worked in a factory, started selling hot dogs out of the back of a truck. He was so successful that in 1950 he quit his job and opened the current Henry's a few blocks from his mobile location. The ceramic stripes on the building and the distinctive sign were added to compete with a modern McDonalds that had opened down the street.
The Cindy Lyn Motel has been operated by the same family since it opened in 1960. It was the last motel before entering Chicago, and the original rate was $6.18. It had 18 rooms, but now has 65 rooms, including some hot tub suites and a fireplace suite. Be advised: Today you can get hourly or nightly rates.
The Castle Car wash dates from 1925, so it pre-dates Route 66. It started as a gas station and housed several other businesses until it closed in about 2004. Restoration rumors have been around but nothing has come of them.
Al Capone's headquarters moved to the Hawthorne Inn at 4833 W 22nd St in in Cicero when Al fled Chicago to avoid the law. On September 20, 1926 (52 days before Route 66 was commissioned), the Northside Gang led a fleet of cars to machine gun the Hawthorne's ground floor restaurant in an attempt to rub out Capone and his senior henchmen. Dean O'Bannion, Hymie Weiss and Vincent Schemer Drucci reputedly were involved. Nearly 1,000 rounds were fired, but miraculously, no one was killed.
Capone got his revenge. In separate shootings later that year, Dean was shot inside Schofield's Flower Shop, and Hymie got machine gunned outside Schofield's. The Schemer was killed in 1927 while riding in the back of a police car after an arrest for kidnapping some supporters of an opposition mayoral candidate.
The Hawthorne Inn closed in 1970. The space is now occupied by a bank parking lot.
Today, Cicero is a town of about 100,000 people. In contrast to its outlaw past, it was the site of a civil rights march led by Jesse Jackson.
From Cicero, stay on Ogden Ave to Berwyn