Chicago, on the shores of Lake Michigan in the State of Illinois, is one of the largest cities in the US. Known as the windy city, and for good reason, it is home to the Willis Tower , the Magnificent Mile shopping area, Navy Pier and of course the Chicago bean. This city really took me by surprise and is well worth a visit. It’s safe to say I definitely had a few people who were surprised that we were visiting Chicago and actually advised us that it wouldn’t be the safest place to stay and to be careful, however I really really enjoyed Chicago and would honestly love to go back. I came here in the summer of 2024, and here are a few things I wish I knew before my visit.
You do not need to use the subway to get around. It is an easily walkable city, however the subway is super convienent and can take you everywhere you need to go. There is also no need to get a car. You can take the L train from the airport directly into the city, which is super convenient and a much cheaper option than getting a taxi.
Take the time to get out of the city on the train. As huge Home Alone fans we decided to visit Winnetka which took around 40 minutes from the Ogilvie Transportation Centre using the Union Pacific North line,. We went there specifically to see the Home Alone house, but had we had longer to explore, we definitely would have spent more time wandering around Winnetka, instead of just going from A to B and then back into the city again.
This one might take you by surprise. Visit the beach - yes you can see the beach from the Chicago 360 and it will honestly surprise you when you think that Chicago is on a huge lake and not the open sea. To me, it really reminded me of Florida and the beaches along the coast. It looks seriously impressive from the sky bar of the Chicago 360 and I wish we had had more time to head down there and see more - maybe next time!
Please do try the deep dish pizza. This is not some fad, it is not overhyped, it is worth that all important spot in your itinerary. We visited Lou Malnati’s as it was one of the most recommended spots for it, and it did not disappoint. We also got the bruschetta to start and shared a a tiramisu which was absolutely delicious. Just remember, it is meant to be eaten with a knife and fork, you will not be able to pick it up! (Unless you’re having it as left overs the next day… which in my opinion, still tastes pretty good!). Go smaller than you think too as it is seriously deep and very rich - they are more than happy to box up what you cannot eat.
Leave time in your schedule to visit Navy Pier - we did not realise that it closed at 10pm as a lot of the pictures you see online are of the wheel lit up at night, so we assumed it would be open a bit later in the evening. As we had an 8pm dinner reservation, we ran out of time. It has the usual array of shops, amusements, a big wheel and restaurants, but is definitely a postcard stop on your trip. We would definitely prioritise this if/when we go back to Chicago.
If visiting the Chicago Bean, be aware that although it is in a public park there is a security line where you have to get your bag checked before you go in. This is not a problem, but definitely could cause some delays if you were on a time crunch as you can’t just walk straight in like you would in a typical public park, It is free to get in though, so it’s purely just a security precaution. Just something to bear in mind if you are short for time. Considering we visited in August, the queue wasnt that long, and we did end up queuing again to go back in, as once we had left, we realised that there was a tourist shop and of course we just HAD to go in to get a magnet!
Chicago is known for its beautiful architecture and if there’s one way to experience the city in all it’s beauty, it is a sunset river cruise! You may just walk past the buildings and not even look up, and even if you do, you probably won’t have a clue what you’re looking at. It’s fascinating to learn about the history of some of the buildings too. We booked an architecture river cruise through Viator which happened to be around the time of sunset, and it was truly breathtaking. This was by far the highlight of the whole Chicago trip for me.
If you are going to the Chicago 360 for the tilt experience for the instagram pics, you will be disappointed. This is a fun thing to do in Chicago, both me and my mum really enjoyed it, however the pictures are a little disappointing. They take a quick photo of you before the tilt experience and you then buy them at the end - they put a fancy background on and charge you about $15! You are not given the option to take photos or videos yourself whilst doing the tilt. It’s definitely not like you see on TikTok! The ‘tilt’ is not as bad as you think, and I would say that even if you are a little afraid of heights, you will be fine - you are completely in control. If the tilting is too much for you then you can literally step back and stand up. Like I said, I would definitely recommend doing it, but if you have seen it all over TikTok like I did, just remember that it’s not exactly how it will be for you. I won’t lie, I was a little disappointed as I love having pictures of everything as a souvenir.
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