The weather had changed, we woke to a red sky dawn in Niagara Falls and a forecast of rain for our 522 mile drive to Chicago. We crossed the border from Canada to USA after the Ambassador Bridge over the Detroit River, with 283 miles left to go.

Ambassador Bridge Canada USA border ner Detroit

We decided not to declare “Brian” the Canadian beaver who had hitched a lift from the last services. The rain didn’t let up until we were passing through the state of Michigan, where we stopped for lunch at an Applebees. The temperature was the highest we’d seen so far this trip at 55 °F. We had crossed the first time zone of our journey, we are now on America Chicago (USA Central Time). We start to realise the immense size of this country, when our sat nav tells us we have a right turn coming up in 245 miles, before we leave the I-94 W. We reached Chicago after 11.5 hours, all of us felt ok, despite the distance, we’d had some interesting debates, and fun challenges like naming the 50 states of the USA from memory along the way, as well as some tunes.

Chicago by night

We are staying at the Hyatt Centric Chicago in a King Room (1633), it’s a fantastic location, just off the Magnificent Mile which is mega for shopping, and close to Navy Pier & the 360 Observation Deck (previously known as the John Hancock Center). We had time for a walk to stretch our legs and find our bearings as dusk fell.

Ginos East Chicago

We dined at Gino’s East, a trendy pizzeria which opened in 1966, the restaurant walls are full of graffiti, with diner’s encouraged to add their mark before leaving. I know we should have been trying their famous deep dish pizza, but we wimped out and ordered the thin crust Chicago Fire ( hot & spicy sausage, fire roasted red peppers, red onions), even that was quite thick.

Chicago is the start / or end of Route 66 depending which way round you’re doing it. We had a day to explore this city before we started to head South. We started by heading to Lou Mitchell’s diner for breakfast, this family business was started in 1923 by Uncle Lou’s father and this Chicago institution is still pulling in the punters, 95 years later.

Donut holes at Lou Mitchells

There’s lots of Route 66 merchandise at Lou Mitchell’s we bought a t-shirt with the route on, and was given a copy of the Illinois Route 66 Visitor’s Guide. For breakfast I tried the buttermilk biscuits and sausage gravy, it was an interesting combination, the biscuits are similar to plain scones, and the gravy was like a thick, creamy soup with sausage bits in it.

I loved their generosity, the ladies received a little box of milk duds (chocolate covered caramel toffee, and everyone was offered a fruit bowl with orange and prune, plus donut holes!

Route 66 Sign Chicago

After breakfast we set off to find the Route 66 start and finish markers, there are a few of them. The historic end route sign is on the intersection of Jackson & Michegan. The new Route 66 sign was on W Adams & Wabash St junction.

Cloud Gate Bean Chicago

We used the Big Bus Tours again for a hop on, hop off circuit of the city. Visiting Cloud Gate / Bean and 360 Observation Deck which was previously known as the John Hancock building and the tallest in Chicago. Entry is $21 on the door and $7 extra for the Tilt experience which is fantastic value when comparing the entry cost of similar attractions in New York.

Lake Michigan Beaches 360 Chicago Observatory

It’s hard to remember that Chicago is situated on the shore of Lake Michigan, and not on the coast when gazing down on the beaches.

Our last meal was at the Big Bowl, which is an excellent restaurant for Thai and Chinese gastronomy in Chicago.

Tomorrow we leave Chicago to drive to St. Louis and the first leg of our Route 66 tour.

Mike’s Thoughts

I don’t think we really got under the skin of Chicago. Perhaps we didn’t have enough time there. The setting, in Lake Michigan is stunning. In fact, it feels more like an ocean side city than a lake side one. The lake extends far beyond vision, so is more like an ocean.

I sort of expected it to look and feel like the gangster city from the 1930’s movies, but the reality is it looks like most other modern cities, with lots of skyscrapers. We did a bus tour which seemed to focus on the elevated railway, which is very cool, and we got the amazing 360 degree view from the tallest building in the city, and were tempted by some tours of the old gangster district, but in the end time caught us out.

Maybe we should go back one day.

You can see our photos from our time in Chicago here: Chicago Photo Album