2022 Chicago Trip

Day 1: Nervous, but ready to go!

We’re back for this years New Year New Place trip, and this time, we’re going to Chicago! If you don’t know what New Year New Place is, I made a goal when I was 20 to try and go somewhere new each year. So far I’ve done it every year since, and I always blog my entire trip while I’m there.

This year we’re spending the weekend in good ole’ Chicago! I often get asked why I go the places I go or how I choose where to go and truthfully, it all depends on price and timing. I usually search for the cheapest place to go and narrow down the list of options to what I haven’t done before. Once I’ve chosen where I’m going, I start planning from there.

The last couple of trips I’ve taken have been with friends or family, but this year I’m traveling 100% solo. I feel like it seems I travel these trips alone a lot, but I’ve actually met people I know in every place I’ve gone. So while I might be flying alone, I haven’t really been alone.

The only time I’ve really been alone was my first ever trip, when I was 20, and I started in Washington DC. If you know, you know. It was a complete shit show thanks to having no understanding of how public transit works, a phone that died on 50%, and a gps that only worked half the time. It was an adventure for sure. Luckily, I was only there for a day, so the ‘adventure’ was fairly quick.

6 years later, here I am spending a weekend in a popular city by myself. I’d be lying if I said I wasn’t nervous.

One one hand, I feel like I’m so much older, smarter, and experienced than I was the first time. So I’m confident everything will be smooth and fun. Technology has advanced in 6 years so hopefully I’ll be able to more easily navigate public transit with the help of in-real-time apps and digital train passes. My phone doesn’t die randomly, and I’ve since invested in a portable charger that goes everywhere with me. I’ve looked up top places and have a decent idea what I want to do. I am excited for everything this trip will be.

On the other hand, I’m a young, petite girl traveling on her own to a city that could be considered debatable depending on who you ask. The world has changed a lot and has proven to not be as safe as it once was, so being vulnerable is scary. However, I know that I can do it. I am strong. I am independent. I am aware. I can do anything. You have to get comfortable with being uncomfortable, and it’s been a little bit since I have been, so here we are.

And even if this trip is the complete opposite of how I intend and is a total fail, at least it was good for the plot.

Now that we’ve gotten all that out of the way, let’s get this trip started!! I’ll be in Chicago until Monday afternoon so I have an entire weekend to sight see.

I actually had no idea Chicago was in a different time zone until I realized I was still in the air at the time I thought we were supposed to land. So I landed around 8pm their time, but 9pm my time for the east coast.

The flight was standard, luckily not too much turbulence. The only complaint I have is the fact that my ears kept popping/not popping which is weird since I don’t usually have ear issues when flying and someone had seriously bad gas. Both of which left me semi nauseous by the time I made it into the airport.

Once I unboarded, I followed the signs for the trains to the city. I already had the transit app downloaded to my phone with my pass so I could easily get on/off without having to worry about paying each time or getting a ticket. I was about to scan my pass when I asked the worker at the station if this would get me to the bus # I was looking for. She told me to go down to a different terminal so I could get on for free instead of having to pay. I followed her directions and eventually ended up at a terminal. I wasn’t at the same number terminal she had told me, but thankfully there was a worker there who approached me asking if I knew where I was going. I pretty confidently said “nope” and showed her my phone for where I was trying to end up.

She gave me directions that seemed pretty straight forward so I could ensure I was getting on the bus that I needed to be on. Buses are confusing, and even though I thought I’d be able to see the routes in real time, I was wrong.

According to my app, my bus should be leaving at 8:47, I’ll get off the first stop, and a few minutes later get onto the next bus that’ll get me to the hotel. It’s 8:52 now, I’ve confirmed it’s the right bus number, and I’m just wondering why we haven’t left yet. The bus driver got off and I haven’t seen him come back, and I start to question if I actually am on the right bus. Eventually, he came back and we were on the way.


I get off at the next stop and should be just in time for the next bus. It’s scheduled to come at 9:11, and I have a few minutes to spare! I walk closer to where I’ll be getting on so I can wait. And wait I do.

It’s now 9:20, and my app has updated that the next bus isn’t until 9:40. I suppose that either means the bus didn’t come at all or I had just missed it (probably while the last driver was mia). I hang out and look at the route on my phone so I know exactly what to do when it arrives. I look up from my phone to see very faint wording on a sign saying there are no more buses to arrive in the next 60 minutes. I’m very confused because I have two different apps that show a bus coming at 9:40, yet this says otherwise. I go to the website for the bus company noted on the sign and, sure enough, it says the next bus is 11:30pm. What is going on?!

I was started to get a little worried that they weren’t showing the same thing and looked up lyft rides just in case I decided to bail. I was initially going to take a lyft to the hotel since my app said I’d have to walk about 15 minutes from the bus stop to my hotel, and I wasn’t too keen on doing that alone in the dark. But once I saw lyfts were $60 (!) I decided I’d be taking on public transit. It was about $30 once I mapped it from where I was. I figured I’d wait until 9:40 since it ideally should be coming then, and if it didn’t, I’d just pay for the lyft.

Luckily, at 9:30 the bus showed up! For some reason the bus pass that I purchased didn’t seem to be working when I was scanning it on my watch (even though it should’ve), so I’ll have to figure that out by tomorrow so I don’t have any issues… I can’t imagine every driver will let me on like the 2 tonight did. (I assume they didn’t know/remember my pass didn’t work?) I switched it from my watch to my phone, so I hope that works.

My app shows the last stop on this bus before my hotel is about a 20 minute walk. I decide I’ll just get off at that stop and lyft to the hotel from there since I’d at least be closer. We’re nearing the last stop shown on my phone, when the driver goes right past it. A few people stand up and let him know they’re getting off at the next stop, so I’m (once again) not sure what’s going on since I’m not showing any more stops.

I decide I should probably just ask him where to get off so I don’t end up in the middle of nowhere since it’s taken me long enough to get to this point, and I’m ready for a shower. He lets me know that since there’s a foreign couple also going to the same hotel as me, he was going to stop right across from the hotel so we just have to cross the street.

Plus side of that, I don’t have to lyft or walk very far to the hotel.

Cons of that, I had to cross a highway (not a street), and now I have no idea where the closest bus stop is. I’m thinking the front desk at the hotel should be able to help me with that, and since I won’t have my luggage with me, I imagine it wouldn’t be a problem to walk there. Guess I’ll find out in the morning…

It took me a little over 2 hours to get to the hotel from the time I landed, but I made it! I’m now showered and writing this so I can post it before heading to bed. I’m hoping to visit The Bean first thing in the morning so I can beat the crowds. Keep your fingers crossed for me!

Thank you for reading, talk tomorrow ❤


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