Chicago has been a place that I have wanted to visit for a number of years, although I have never been able to quite pin-point why. Maybe it was because The Windy City has been dubbed as the second New York of the USA, but with a little more comedic value. Or maybe it was the glamour of the old school gangsters, Al Capone and the Prohibition. Either way we had decided early on that we wanted Chicago to be one of our first stops when it came to planning our six-week road trip. 


The Silver Palm Restaurant – This eatery is in an old train cart, converted to sell it’s famous Three Piggy Sandwich. It had a really cool, easy vibe and I enjoyed a lovely salad with mac n’ cheese *balance*. 

The Windy City Café – A cute little café on the outskirts of Chicago downtown. We enjoyed a hearty breakfast, which set us up perfectly for a day of exploring the Windy City. 

Lou Matianos – We had been recommended to go here ourselves by a few of the locals so on our last night we headed out to try this award winning Pizza. Lou’s is well known for it’s butter-milk crust, so we ordered that as a base for our classic peperoni pizza. Oh my, it was fantastic and I wish we hadn’t waited until out last night so that we could have gone back for more!


Madison Avenue – we stayed on Madison Avenue, which was about a half an hour walk to downtown Chicago. We ended up getting Lyfts everywhere just because it was so cold (and also because James is a wizard and found some great money off promo codes!) but it was a really safe and quiet area to have as a base.

Air BnB – This was our second Air BnB stay of the trip, and again, it did not disappoint. Our host was so lovely and we even had a little cat to look after whilst we were there. 


Watch A Comedy Show – Can you really go to Chicago and not go to a comedy show? We were really lucky and stumbled upon a really cool bar that hosted a comedy night every Wednesday. The show is called, Comedians You Should Know About and it showcases five or six up and coming comedians. Tickets were only $5 online and it was such good value for money. James and I shared a pitcher of beer and laughed until we cried – literally, I had no makeup on by the end!! 

Eat Pizza – Although I have mentioned a great place to it proper, Chicago Pizza, it really is something to go and do whilst you’re visiting the city. It is definitely something to tick off your list, and if you’re a pizza lover like me, you certainly won’t regret it. 

Navy Pier – I was slightly disappointed that we weren’t able to see Navy Pier in it’s full glory. As we went in March, the fairground, lights and outdoor entertainment wasn’t there, and a few things were shut due to it still being classed as winter. However, looking back over the city’s skyline was pretty cool and well worth a look. 

The Chicago Bean – This is a must see as it one of the most pictured things in Chicago. However, we walked from Navy Pier, took a few pictures and felt as though it was ticked off of our list. It is definitely a ten minute job, but it is worth seeing and is located in Millennium Park, which is really pretty to walk around. 

Lincoln Park Zoo – The first thing to mention is that it is free! Yes, really! It is a truly amazing zoo made all the better that you can enjoy everything it has to offer without spending a penny. There is a huge selection of animals, a lot of them being rescued, and they have lots of room and great living quarters. They have a feeding/talk schedule that I would really recommend having a quick look at before hand as they are definitely worth attending! 


Bridges To Downtown – Especially at dusk or when then sun is about to set… There are a number of bridges that will take you from main Chicago across to downtown, which is where the majority of the shops, the zoo, Navy Pier etc. are located. But the views of the buildings as the sun starts to set really are pretty. 

Dunkin Donuts Pink Chair – Although maybe not the most glamorous of locations, on our last day in Chicago we popped into a Dunkin Donuts at the end of the street we were staying on and found this beautiful, pink, bucked seat. I fell in love and as I had pink lipstick and my cute Oliver Bonus hat on, I made the excuse to take a picture or two for the gram. 

Millennium Park At Sunset – Much like the Brooklyn Bridge, Millennium Park in the heart of Chicago, comes to life once the sun begins to dip below the tops of the skyscrapers. There is just something about the orange glow of that time of day that hits everything just right and makes it a perfect location to take some shots for Instagram. 


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