Take the shuttle or a taxi to The Drake Hotel in Downtown Chicago and check in to your luxurious room. An EagleRider Tour Leader will be in the hotel lobby from 4pm to 6pm to greet you and take care of a few small details before we make the short journey to the birth place of Harley Davidson in the morning. Tonight you will have the opportunity to meet your fellow Pre-Riders as we enjoy our first of many great meals together at a lively restaurant in the heart of “The Windy City”.

We'll get an early start this morning and head over to Union Station in Downtown Chicago to catch our train to Milwaukee. We will be back at The Drake Hotel tomorrow night so feel free to leave your large bags with the bell desk if you wish to carry an overnight bag to Milwaukee. This is a short 92 mile train ride with a lot of charm and scenery along the shores of Lake Michigan. Upon arrival in Milwaukee we will check in to the famous Iron Horse Hotel and make the quick walk across the street to enjoy as much time as you like at the HD Museum. Your VIP museum entrance fee, a great lunch and private behind the scenes tour is included in your package so you'll have plenty of cash to spend in the HD gift shop! Tonight we'll enjoy the sights and sounds of downtown Milwaukee, and maybe even take in a baseball game if the Brewers are in town.

Don't worry if you didn't get to see and experience all that the HD Museum had to offer yesterday, as we have plenty of time this morning for you to walk across the street and see your favorite parts once again before heading to Chicago around noon. Upon arrival in Chicago you will have some time to relax or enjoy a walk along the river or Navy Pier before meeting up with the remainder of your fellow riders who will be joining you on the Route 66 guided tour. Tonight we'll have a great dinner and dream of what is to come!