If I could travel to Chicago

I am (well maybe not so much anymore…so maybe instead its more of an I used to be?) a planner. I plan what I need, things I need to do, books I want to read…I pretty much just make a lot of lists…and so the tale begins.

In early June (late May?) I thought about having an adventure at the end of my summer break because I wouldn’t be able to go anywhere during the beginning and end of summer because of work and an internship. I’ve fallen in love with Chicago over the past few months so I thought that visiting the city would be a great adventure! I set out on my plans and well it turns out I probably won’t be making it there this summer after all (I’ve honestly cried about this a few times this week already…).

So to look on the (kinda) bright side, I already have a good structure for a trip when I get around to having the chance to go. I wanted to share the ways that you could get to Chicago and places where you can lay your head at the end of the night. I’m also going to write a post about some of the things I would go see if I could make it to Chicago, so look out for that!

how to get there and where to stay

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  • I made sure to sign up for email alerts from TripAdvisor because I was toying with the idea of flying to Chicago instead of driving (which isn’t too bad its about a 7-8 hour drive from where I live). I just really love airplanes and the whole flying experience so I was keeping that option open. They had some really good deals for July and August with round trip tickets that were as cheap as $80 (yes I have cried about not buying a ticket when I first saw them). You should totally sign up for email alerts if you plan to travel anywhere! I can only recommend TripAdvisor because that’s the one I have had first-hand experience with.
  • I fell in love with trains while in Germany last year and thought it would be a fun idea to go on a train ride to Chicago! How cool would’ve that been!? It would take a pretty long time to get there and because where I live has no trains I would first have to take a bus for about 6 hours (which means more like 7-8…sometimes anyway) and then go on a train for 5 hours. Hey it could still be a possibility if I left like really really early and then got there at a decent time in the morning so I would still have plenty of time during the day for sightseeing.
  • I spent a lot of time on Airbnb and found an adorable place that is a bit out of Chicago. It was the perfect mixture of old and new put together and it had such a nice view. Sadly it has been booked for the weekend I was thinking about going but its okay maybe next year….though it is open for the week before I wanted to go. Nobody take this rental please!! Until I for sure now I’m not going.
  • I also looked a bit into the hostels in Chicago and found two that I thought would be pretty nice to stay in. One says its the only hostel in downtown Chicago and the other one is advertised as a hipster place (which I ain’t complaining about). They both look really nice and you can stay at each of them for under 200 for 3 nights! Yes, the rooms are shared with other people but you know what you gotta try new things right?



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