Day 3 – Chicago, Illinois
After a good night’s sleep and finally getting over some of the travel fatigue, we were up and ready to kick off our American adventure properly. Today was all about ticking off some Route 66 essentials, collecting our trusty Harley-Davidson and getting a few more miles under our belts. Well, technically, we had to collect the bike first!
Breakfast at Lou Mitchell’s – A Route 66 Tradition
First stop was a trip into Chicago for breakfast at Lou Mitchell’s, a Chicago institution that has been serving hungry customers for more than 100 years.
If you’re starting your Route 66 journey in Chicago, this place is pretty much compulsory. You can’t just rock up, point the bike west and claim you’ve done Route 66 without first paying homage to a few of its traditions!
Lou Mitchell’s is famous for its breakfasts and its long association with the Mother Road. It’s the sort of place that makes you feel you’re part of the history before you’ve even travelled your first proper mile.
With breakfast sorted, it was time for the obligatory photos at the Begin Route 66 / End Route 66 signage. Naturally, no Route 66 adventure would be complete without photographic evidence that we’d actually made it to the starting point. After all the planning, we were finally here!
Picking Up Our Harley-Davidson
With our bellies full and the sightseeing duties completed, we ordered an Uber and headed off to EagleRider to collect our hire bike: a Harley-Davidson Ultra Limited.
Now things were getting serious. We’d travelled halfway around the world, and it was finally time to get out on two wheels and experience a little American freedom.
There was another mission to consider as well. We were completing the Harley Owners Group’s ABC’s of Touring, so we needed to make the most of our time in the area. A ride across the state line into Michigan was just the ticket.
Our little excursion would see us tick off the borders of Illinois, Indiana and Michigan on our touring list. Three locations added to the tally before we’d even properly started our Route 66 journey. Not a bad day’s work!
Lunch in Michigan – The Stray Dog Bar and Grill
By the time we’d completed the bike collection and got ourselves organised, lunchtime was fast approaching. Fortunately, we’d already picked out a destination.
We headed for The Stray Dog Bar and Grill in New Buffalo, Michigan.
It was a good excuse to stretch the ride, cross another state border and enjoy a feed before pointing the Harley back towards Illinois.
There’s something satisfying about being able to combine a motorcycle ride with a decent meal and a few touring goals. We weren’t just riding for the sake of it; we were knocking over items on the ABC’s of Touring list at the same time. Very efficient, if you ignore the fact that it also gave us another excuse to stop for food!
A Stop at Illinois Harley-Davidson
After lunch, we made our way back towards Willowbrook, stopping at Illinois Harley-Davidson along the way.
A Harley dealership visit is almost a touring ritual in itself. There’s always something worth looking at, even when you’ve already got a perfectly good Harley underneath you.
Eventually, we made it back to the Econo Lodge, giving us a chance to freshen up before heading out again for the evening.
Dinner, Pints and a Route 66 Icon
We returned to The Kerry Piper for another visit, having enjoyed our first experience there the previous evening. It was already shaping up to be one of our favourite local haunts.
We also made a stop at Dell Rhea’s Chicken Basket, another iconic Route 66 establishment with a fascinating history.
The Chicken Basket’s story began around the late 1930s or early 1940s, when it operated as a lunch counter in an old gas station. From those humble beginnings, it became one of the well-known stops associated with the Mother Road.
That’s one of the things we love about Route 66. Behind many of the diners, motels, petrol stations and roadside attractions are stories that stretch back generations. These places aren’t simply somewhere to grab a meal; they’re part of the history and character of the road itself.
And, of course, any place with a long history and a reputation for feeding hungry travellers deserves a look from The Thirsty Tourists!
Three States Ticked Off and the Adventure Begins
Day 3 had been a busy one. We’d enjoyed a traditional Chicago breakfast, photographed the Route 66 starting point, collected our Harley-Davidson Ultra Limited and ridden into Michigan to tick off more locations for our ABC’s of Touring challenge.
We’d also visited an iconic Route 66 eatery and managed to fit in a couple of familiar local stops.
Tomorrow, we’d be ready to get stuck into the Mother Road properly. The bike was sorted, the adventure was underway, and there were plenty of miles, roadside attractions and watering holes still to come.
Route 66, here we come!
#TheThirstyTourists #TouringIsThirstyWork
