Day 4 of our coast to coast Trek America tour and we were up early to leave our Ohio KOA cabins and begin our journey to Chicago.


Our first stop to day was just across the border of Indiana state in the Amish town of Shipshewana. I’m not exactly sure what I expected but it wasn’t what we got. Shipshewana was in many ways a typical American town like any other I’d visited. Except for the occasional horse and cart rolling down the streets and the odd person in traditional Amish dress passing by. With it’s Amish market selling handmade food and crafts and the opportunity to take a ride on the traditional horse and carts, it felt like a very touristy look at Amish life rather than getting an accurate snapshot but we enjoyed wandering around and especially enjoyed the homemade ice cream we purchased before leaving to continue our journey.


We had one more stop before arriving in Chicago, Illinois – at the childhood home of Michael Jackson in the town of Gary, Indiana. The house had become something of a shrine with fan messages and gifts covering the gates around the house.
Tributes to Michael Jackson The house where Michael Jackson grew up
Then it was on to Chicago where we were staying at the HI Hostel in the Loop area. It was late afternoon by the time we arrived so as we got ourselves settles into our rooms – it was a really nice hostel and us girls had our own en suite dorm! – deep dish pizza was ordered in from a nearby Gino’s East area which we ate down in the common area. Having had Gino’s deep dish fresh at the main restaurant in the past, I didn’t enjoy the take out pizza as much and many of the others in the group were unimpressed.

That evening most of us had taken up the option to take a bike tour of Chicago, something I’d not done on my previous 2 visits to the city. Short on time, we caught taxis uptown to the headquarters of Bobby’s Bikes where we were each provided with hi-vis jackets, helmets and a bike before setting off to follow our tour guide. Our first stop was on the shore of Lake Michigan but unfortunately the fog had moved in over the city obscuring any views we should have had. Then we rode uptown to see some of the huge mansions including the original Playboy mansion.
Fog obscuring the view of Lake MIchigan The original Playboy Mansion ‘Corn Cob’ Towers Chicago Riverside

We were all a bit nervous when told we’d be riding on the main road alongside all the Chicago traffic for the next section of our tour but it was less scary than it sounded and we paused for photos down by the Chicago river before cycling back lakeside and down to Millennium Park to see the amazing Cloudgate sculpture then further south past Grant Park to the museum campus where, completely coincidentally, fireworks started going off at an event being held there just as we arrived.

Bike tour over, we walked to the Hancock Tower where the rest of the group were having drinks in the sky bar. We joined them for a drink but left shortly after as the cloud meant there was zero visibility and it was an expensive place for drinks when there was no view! Instead, we walked back to the hostel and spent the rest of the evening in the common room playing table tennis and pool.


The next day we had a full day in Chicago to do what we liked. Most of us decided to use it to try and see as much of the city as we could in a day and as I’d been before and vaguely knew my way around, I lead the way. We started at Willis Tower, formerly Sears Tower, once the tallest building in the World. The queues for the viewing platform weren’t too long so we bought tickets to go up and spent some time enjoying the views over the city.

Next, we walked back towards the lake and visited Grant Park to see Buckingham Fountain. There was a food festival going on in the park so we stopped for a few free samples as we walk through towards Millennium Park. At Millennium Park, we stopped to see Crown Fountain, also known as the ‘spitting’ fountain as digital faces each end appear to spit water out at regular intervals. Then we walked back to the Cloudgate Sculpture which we’d seen on our bike tour the previous night but is always a fun place to visit in the city as you can see yourself reflected in it!
Crown Fountain Cloudgate Sculpture Chicago River
Next up was Navy Pier where we had lunch at the huge food court before taking a boat cruise on Lake Michigan. The pier has a few fair rides so as lunch had gone down, we took a ride on the flying chairs.

From Navy Pier, we walked back alongside the Chicago River to Michigan Avenue, also known as the Miracle Mile. Similar to New York’s Fifth Avenue, this is where all the big stores are and we spent a while browsing in the shops as we went past.


Getting hungry again, some of the group decided to go to the Cheesecake Factory in the Hancock Tower for food while two of us decided to give deep dish pizza another go, this time at Gino’s East restaurant. Eating the pizza at the restaurant made a huge difference and this time, it was just as good as I had remembered!
Walls covered in grafitti at Gino’s Chicago Deep Dish
It was evening by the time we all met up again and the sunshine had disappeared and been replaced by big, black clouds. As we walked back down Michigan Avenue, it started to pour down with rain causing us to decide to call it a day and run back to the hostel to shelter. But we’d had a fun day sightseeing in the city and managed to fit a lot in in a short time.
Watch my Trek America adventures in Chicago here: