Chicago: It's my kind of town. It has a lot to do that has nothing to do with Route 66, and we're not going to attempt to tell you all those things here. We have listed classics like some gangland sites, Wrigley Field and a few must see historical buildings, but mostly you will be on your own. Have fun exploring Chicago.
Chicago is the home of the Outlaws MC. There are three chapters in Chicago and chapters in many of the surrounding towns..
The Congress Plaza Hotel on Michigan Avenue is a great Route 66 era hotel. The rates are cheap by Chicago standards and they have secure parking for motorcycles around back. There is a cool lobby bar with good drinks and food. It is within walking distance of many Chicago landmarks, including the Buckingham Fountain in Grant Park across the street (which is the fountain in the opening credits of Married with Children. Plus, it's only a few blocks from the corner of Adams Street and Michigan Avenue, where you will see the "Begin Route 66" sign and start your adventure.
There are lots of biker bars in the Chicago area, but not many close to downtown. The Twisted Spoke is a popular one. It was busy the night I went, but I was the only one wearing a Club patch, and there were few bikes outside. Even so, it was fun. It has a huge selection of liquor. There are several pages of bourbons alone. Wednesday is half price night. It also has an extensive menu, and is open for breakfast, lunch and dinner.
Delilah's, Kuma's Corner and Hogs & Honey's are other popular Chicago biker spots.
Miller's Pub is a Chicago landmark within walking distance of the Congress Plaza. It has hundreds of photos of Chicago athletes and an old wood bar. They are known for their ribs. It also is near the Palmer House Hotel, which has one of the best bars in the world. Don't miss it!
Everybody always talks about Lou Mitchell's Restaurant, which has been in its Route 66 location since before Route 66 opened. They give away free Milk Duds to the ladies. It's a great place to have breakfast before heading out on the Mother Road. You will not leave hungry.
Getting out of Chicago is surprisingly easy even during peak traffic hours. Route 66 originally began on the corner of Michigan and Jackson Avenue. Today, it starts a block over on Adams Street, which goes one way out of town. You'll go through the heart of downtown Chicago, and wind through some nice tree-lined neighborhoods on your way to Ogden Avenue, where you'll go left heading toward Cicero. You're on your way!
Get on Adams St at the corner of Adam St and Michigan Ave - Follow Adams St all the way through Downtown Chicago to Ogden Ave - Go left on Ogden Ave and head toward Cicero