Things I Wish I Knew Before Travelling to Chicago

Updated: Jun 10

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 be warn me about going as they felt it wasn’t the safest city to visit, however this was actually somewhere I really really enjoyed 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 there is a subway system and it is super convienent and can take you everywhere you need to go within the city. I can definitely say that there is no need to get a car. You can also get the L train from the airport which takes you 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 - Union Specific North - we visited Winnetka which took around 40 minutes from the Ogilvie Transportation Centre. We went here 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 as it seemed to be a lovely little town.

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 remember that Chicago is not on the sea, but on a huge lake! From the 360 it looks like you are looking down onto a Florida beach! It really does look seriously impressive from the sky bar at the 360 tilt tower and I wish we had more time to head down there, and see more - maybe next time!

Try the deep dish pizza. This is not some fad, and trust me it is not overhyped! It is well worth that all important spot on your itinerary when visiting the city. We went to Lou Malnatti’s as it was one of the most recommended spots for it, and it did not disappoint. We also got the bruschetta to start (8 pieces!) and a yummy tiramisu to share for dessert which was 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!)

Leave time for 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, and after our 8pm dinner reservation, we just ran out of time. It has the usual array of shops, amusements, a big wheel and restaurants, but is a postcard stop on your trip. We would definitely prioritise this if/when we ever go back to Chicago.

If visiting the bean, 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 with a typical public park. It is still free to enter, so clearly this is just a security precaution. We went in August time, and the queue wasn't that long, and we ended up queuing again to go back in, as once we had left, we realised that there was a tourist shop and we 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 its beauty, it is with 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 did this by enjoying a sunset cruise along the river, and it was breathtaking. By far the highlight of the whole Chicago trip. We booked our sunset cruise through Viator as usual, closing the buy now pay later option, with the monies being taken from your account two days before, and the tickets being released onto the App.

If you are going to the Chicago 360 and paying the extra $10 each for the tilt tower experience, say just for the instagram pics, you will be disappointed. This is a super fun experience to do in Chicago, me and my mum both loved it. Even if you are afraid of heights I would honestly still recommend the experience because you are completely in control of the whole thing. If it gets too much for you, you can just take a step back. However, when it comes to the photos, they take a quick picture of you before you get started, and then put a fancy background around it. You don't get any actual pictures or videos of the tilt experience and you are not allowed to take your phones and cameras with you - it really isn’t like you see on TikTok. Like I said, I would definitely recommend doing the tilt for the experience, but if you have seen it all over TikTok like I did, just remember that it is not exactly how it will be for you on the day. I won’t lie, I was a little disappointed as I love having pictures of everything as a souvenir.