General, Travel

Chicago: The Windy City

For those of you who have followed my blog for a while, you may have seen a previous entry for the Windy city way back when I was traveling the world for a year (found here). I loved Chicago on my first visit, it’s safe to say that I feel in love with the place back then, so when I found out that everyone would join up to celebrate for a big finale together in Chicago, I was extremely excited.

It smashed any expectations and any hopes that I had, and was spectacular!!

First, before we even left Indiana, and before we changed to Central Time, we had a final pit stop. Albanese sweet factory makes some of the world’s best candy, and is known for its awesome gummy sweets. We were lucky enough to have a bit of a tour, and got to look into the factory as some of the gummies and chocolate treats were being made. We also got to sample some of the sweets, and I have to say they were tasty. The variety of flavour and combinations of chocolate goodies were incredible. We all left with bags of goodies to enjoy and take home.


Over the road there was also a popcorn shop that sold the biggest variety of popcorn flavours that I have ever seen in my life. There was sweet, savoury, smoky, spicy, and everything in between. I think the shop owners seemed as excited to see us as we were to sample the goodies!

Pat, our lovely, bubbly coach driver is from Chicago, so once we set off towards the city, we could feel her excitement to be home growing. We had a great time with her, she made the journey fun and was an absolute blast. Saying goodbye to her at the Conrad in was actually a tad emotional, we all got a hug in and had put together a collection to say thanks to her!

Last time I stayed in Chicago, I was in a really nice hostel-uni accommodation unit near Millennium Park, and while it was lovely, it was hardly on the luxury end of the spectrum. This time, I was lucky enough to stay in the new Conrad hotel; Siobhan and I were up on the 14th floor and had a pretty cool view of the city and the skyline. The Conrad itself was a really nice hotel. We have been lucky enough to stay at some lovely hotels throughout the trip, and although LeVeque tower in Columbus would remain my favourite, this was arguably the most luxurious hotel we stayed at.

We didn’t have much time to dwell in our hotel, however, as we headed out to Pinstripes for our first meal int he Windy City. I think we all felt a little reflective, I know I did, and sat back to enjoy the first meal in our last city together. Pinstripes was really cool, and actually had bowling and bocce lanes inside the restaurant itself. That was pretty awesome. We headed back to the hotel, decided to have a drink together and prepare the speech that we’d present at the following evening’s formal do. We decided a speech wouldn’t be super exciting, so set about creating a poem full of the highlights of our trip, by the time we headed to our rooms we were all pretty shattered.

The first full day in Chicago was built to be a busy one. At breakfast we looked at our itinerary, planned our day, and thought about making sure Julie had a birthday to remember. We boarded a bus, y’know one of those open top tourist ones, and joined with some other groups to do a tour of the city. The host was great, really funny and knowledgeable, and the interactions between him and Beth were too funny to cope with. We had a bit of a tour along the lakeshore, before circling Soldier Field Stadium (home of the Chicago Bears) to The Field Museum. We had a bit of an intro talk, and we’re given the most amazing bag of goodies (I still use my canvas bag and Sue glasses to this day). I love dinosaurs, so seeing the largest and most complete T-Rex skeleton – Sue – was awesome. I also managed to find something ideal for Julie’d birthday. We got some really great shot pictures outside too, Chicago has a pretty great skyline and with the parks and the lake you can get some really amazing backdrops.

Our next stop was Millennium Park, one end of the big park spaces on the lake edge, and home to famous sculptures and outdoor stages. Cloud gate (or the bean) is pretty recognisable throughout the world, and was definitely the place that we had most fun taking silly pictures with our reflections and generally having a good time before making our way to the spitting face statues and the concert space. I never realised that the parks have their own free, volunteer tour guides that will show you round if you pre-arrange a group tour before you arrive.


Chicago is known for it’s deep dish pizza, and last time I visited I went to an uptown Giordano’s branch. This time, we descended with other groups on the park branch, and tucked into a variety of huge deep dish pizzas. It was also the perfect place to sing happy birthday and gift our birthday presents to Julie. We managed to sit and chill out on a boat tour of the city, taking architectural feats and letting our food settle whilst the breeze cooled us down. We had a little bit of time to shop on magnificent mile where I picked up a World Series baseball before heading back to the hotel to prepare for the formal evening do. I had a nice new dress, and shoes, and I managed to do my hair to make it look semi-respectable during it’s growing out phase. We all looked amazing, and I think felt it too, and set out to the famous Palmer House for drinks, food, and reminiscing.

Palmer house is now a Hilton Hotel, and has huge ornate rooms and meeting spaces. It provided a really amazing backdrop for our formal evening and afforded lots of space for us to mingle and talk about our experiences across the US. We all took turns to share our stories, some groups did speeches, someone did a poem like us, and someone else even did a blind date style wrap up, it was pretty amazing. The food and drink was incredible, and it was an all round amazing night that improved only by winning some flights to the US for a later trip, and by finding out that the after party was to be held at 360 Chicago at the top of the John Hancock tower.

I am not going to lie to you, I had an amazing time. I had the seen The Tilt numerous times on Facebook and was ecstatic that we got to go on it, I definitely spent way too much time going on it again and again and taking lots of pictures. We larked about and generally had an amazing time on our final evening together as a group. It absolutely chucked it down outside, so I joined the hoards (shoes in hand) splashing through the growing puddles and back to our hotels. It was a night never to forget. I decided to stay up and pack that night, preferring the have everything ready rather than get up early, and waited for Siobhan so that we could have one evening chat together before we parted ways.

The following day was spend relaxing and enjoying one another’s company for the last time. We made our way down to Navy Pier and boarded a boat for breakfast. We had some really great food, and although the wind prevented us from getting away from the pier we had a great time. We explored Navy Pier, sat and had a drink, and boarded buses to get to an outlet mall and then the airport.

Chicago, I love you, until next time…

2 thoughts on “Chicago: The Windy City”

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