Day 1: Arrival in Chicago

Chicago as seen from the Willis (formerly Sears) Tower

The flight was comfortable, the food was reasonable and I whiled away some of the time by watching Shutter Island (it’s good). Arrival at O’Hare and getting to the hotel was a different matter. Our travel packs told us to get the shuttle bus or a taxi but we were given so much misinformation at the airport that we gave up on the shuttle bus. We had met up with Simon and Viv on the trek from the aircraft to baggage reclaim – they were carrying helmet bags so they must be planning on doing something similar. Viv smiled at us and said “Route 66?” and we made our acquaintances. The four of us agreed that in order to not waste further time at the airport (we wanted to see something of Chicago that afternoon), we should get a taxi. A lady who seemed to be matching passengers with taxis found us a taxi and agreed that the four of us and all our baggage would get into one taxi. We had our doubts but they were sure. After watching the driver try to shoehorn our helmets into his boot with two more cases still to go, we were right – we wouldn’t all fit so we took separate cabs.

The journey into downtown Chicago took over an hour as the traffic on the freeway was heavy. The driver said that it was because of people coming into town to celebrate the success of their local hockey team, the Chicago Blackhawks, over their rivals, the Philadelphia Flyers, to win the Stanley Cup, a feat they haven’t achieved for almost 50 years. We were impressed with the hotel and the view and were within walking distance of many sights but it was getting late in the afternoon and we had to check in with the tour guide. Besides, it was almost midnight UK time and we were exhausted after a long journey.

The tour guide wasn’t at the desk. It seems that we weren’t given a message that he would be late as he had to take a small group to the Harley Davidson Museum up in Milwaukee. We eventually met him at 6pm when we were given a rucksack, a tee-shirt, a printed tour guide and his contact details should we lose ourselves along the way. The tour guide was Gary Fleshman working for California Sunriders and we would discover how helpful and knowledgeable he would be over the coming days. Gary also has a friend called Bearnard Behr who travels with him and has his own Route 66 blog. We meet our riding buddies at the desk – there will be 8 people on 6 bikes. Simon and Viv will be one couple riding two-up along with myself and Françoise. Then there is Pat, Bill, Dave and Neill making up the eight.

At another desk there are people checking in for a parallel tour from a rival company called EagleRider. They get given smart leather jackets. We wonder how much the tour price was loaded for the jacket and whether the jacket would be good value for the trip. It would be more weight to travel home with and may not be comfortable to wear given the temperatures – in Chicago the humidity was about 80% and the temperature already in the 90s (°F).

We then left to take a quick tour round Chicago – well, as quick as we could make it by going to the Willis Tower (formerly called the Sears Tower) and stopping to take photographs along the way. We had considered a trip on the Chicago River down to Navy Pier but it was getting late and we conceded that we couldn’t do everything. We were also conscious that we were hungry and tired and needed to factor in a meal somewhere. We made it to the Willis Tower and found the entrance on the side to take the elevator to the observation deck. We obviously spent some time there taking photos and enjoying the view before making our exit to go back to the hotel. We were recommended to try the Kinzie Chophouse on 400 North Wells St. since it was close to the hotel and quite reasonable. We couldn’t find it at first (more ambiguity with directions) but eventually found and enjoyed our first steak of the trip. We made our way back to the hotel (it was about 4am UK time by now) and collapsed into bed for a good night’s rest.

Next: Day 2: The Journey Begins

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