A Midwest Road Trip: Chicago

After spending over 6 months planning a self-drive road trip of Midwest USA, the time had finally come to depart for our gateway city of Chicago. Being used to taking either short city breaks in the USA or escorted small group tours for longer trips – neither of which required us to do any of our own driving – it was the first time any of us had undertaken such a trip and we were equally excited and nervous for the weeks ahead.

At the airport waiting to board

To help to calm the nerves, we had chosen to begin our trip with a few (carless!) days in a city familiar to us all – Chicago. The three of us had all spent a few days here as part of the Trek America coast to coast tour through the Northern states we previously taken – the trip we had actually met on – and I had visited a few times prior to this and knew the city pretty well (read my tips for visiting the city here).

After meeting up in the arrivals at Chicago airport (we had all flown in from different parts of the UK), we managed to navigate our way into the city and then drag our luggage the short distance from the subway to our Michigan Avenue hotel. It was already early evening so after checking into our room, the only thing on our mind was food and sleep. We grabbed take away from the first place we stumbled across and then settled down in our room for the night.

Rising early thanks to the jetlag, we began the next day – our only full day in the city – with a stroll along Michigan Avenue up to the John Hancock building. After stopping for breakfast at Starbucks, we continued across the DeSable Bridge and onto the ‘Magnificent Mile’. This area is a shoppers paradise and we couldn’t resist popping into a few of the stores we passed including Dylan’s Candy Bar and the Disney Store.

Above, and below, views from Chicago 360

Eventually, we reached the John Hancock building where we had booked tickets up to its observation deck, now rebranded as Chicago 360. On our last visit together to the city, we had instead visited the observation deck at the Willis Tower but having been up both before, the John Hancock building’s observation deck was my favourite. Feeling adventurous, we had also purchased tickets to try out Chicago 360’s latest attraction, TILT. Branded “Chicago’s newest thrill ride”, here visitors can stand against a glass window on the 94th floor observation deck as it slowly tilts forward over the city below.

It was a clear, sunny day and the views over the city from the top, especially looking towards Lake Michigan, were beautiful. The TILT ride was fun, if short-lived, and not nearly as scary as it looked in my opinion although the screams from other visitors showed that not everyone agreed with me on that!

Walking along Lake Shore Drive

Once back at ground level, we walked east towards Lake Shore Drive, crossing to the path running alongside the lake and following it south past the beaches towards Navy Pier. Wanting to get out on the lake but having taken the Shoreline Sightseeing company’s Lake Michigan cruise on our last visit, this time we opted for a jetboat ride.

With some time to kill between booking our boat trip and its departure time, we walked the pier and had a go on some of the amusements before returning to board.

Navy Pier fun

The jet boat trip was great fun as we sped across the lake twisting and turning, getting us just wet enough to cool us down a bit from the the strong, summer sun without soaking us.

We returned to the pier at a slightly slower pace allowing us the opportunity to take some photos of the Chicago skyline in front of us.

Above, and below, having fun at the Cloudgate Sculpture

Leaving Navy Pier behind, we walked south to Millennium Park, home of my favourite Chicago attraction – the Cloudgate Sculpture or ‘the silver bean’ as we prefer to call it. Here, we spent more time than was probably necessary staring at the reflections of ourselves ad the city skyline in the sculpture, walking beneath and finding lots of different angles to take photos from.

Also in Millennium Park and not far from Cloudgate, is the Crown Fountain and with it being a boiling hot summer’s day, it was full of children – and some adults – cooling off by paddling their feet and waiting for the faces on the screens at each end to ‘spit’ water over them.

Crown Fountain

Having spent all day under the hot, summer sun, and now being almost back at our hotel, we couldn’t resist diving under the jet of water suddenly spewed from the fountain. We were absolutely drenched but it felt so good!

Next stop was across the road to our hotel to change – and to try to dry our clothes before the start of our road trip the next day! – before heading back uptown later for pizza at our favourite Deep Dish restaurant, Gino’s East. As usual, the pizza took a while to cook but we kept ourselves entertained adding to the customer graffiti covering the restaurant’s walls and furnishings!

The deep dish didn’t disappoint and full up, we waddled back to our hotel full of anticipation for what the next day would bring.

This was it, it was time to check out of our city hotel, head back to the airport and pick up our hire car for 3 weeks on the road. We would be back in Chicago at the end of it all having hopefully returned from a fun-filled Midwest adventure!!

11 thoughts on “A Midwest Road Trip: Chicago

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