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Sami

Winter in the Windy City: Chicago, IL - Jan 2023 Overview

Once again I went to Chicago for another adventure. Before the last trip to Chicago ended I was already planning this one to come back to see the Harry Potter At Play experience that was, at the time, opening soon. This started as a solo-trip for the Harry Potter experience and it ended up being a 3-day trip packed full of activities and learning more about one of my favorite travel spots.


In this post, I will give an overview of my itinerary, budget, and overall thoughts on the trip. In future posts, I will break down each day in one or two posts, with each event in detail, and a separate post about the food of Chicago.


Itinerary

  • Friday

    • Flight to Chicago

    • Hotel - Hotel Julian

    • Field Museum

    • Stan's Donuts

    • Lou Malnati's Pizza for Dinner

  • Saturday

    • Walking Tour - Winter Architecture Tour (Birth of the Skyscraper)

    • Harry Potter At Play

    • About Last Knife for Dinner

    • Taylor Tomlinson comedy show

  • Sunday

    • Walking Tour - Winter Loop Tour

    • Shedd Aquarium

Budget

This trip was more than my last Chicago trip, also more than I anticipated, but only because I had more meals to pay for and I bought a few souvenirs.

  • Flight, Hotel, Transportation: $508.42

  • Entries/Activities: $227.52

  • Food and drink: $221.65

  • Souvenirs: $127.35

  • Parking: $60

  • Total: $1,099.94

Friday

Friday started off with an early morning flight. I chose to fly this trip due to the potential for bad weather, being the middle of winter in the midwest This trip was the first time I flew to O'Hare airport and it wasn't for a connecting flight. This trip was also my first time using Chicago's public transportation, which I will talk more about in the next blog post. I dropped my luggage off at Hotel Julian and started walking to the Field Museum, where I spent the rest of my day. I took the train back to my hotel and checked and got settled. Then I headed out for dinner and got a little lost while looking for a place to buy a bottle of wine.


Saturday

Saturday was filled with a variety of activities to keep me busy: an architecture tour that I learned so much on, the Harry Potter: At Play experience that let me dive into my favorite place, and a comedy show that was absolutely wonderful. The challenge on Saturday was keeping warm enough to be able to enjoy the next activity, luckily there are plenty of places in downtown Chicago to step into for warmth and some that also connect to other buildings so you can walk inside for a bit.


Sunday

Sunday was filled with more fun to finish off the trip: a Loop tour that showed a lot of Chicago history and the Shedd Aquarium, which I have been to before, but each time is a new experience. Snow was falling on Sunday through most of the day, really giving me the full effect of winter in the windy city. The way the buildings blocked the snow at different times is something that doesn't happen at home. It really gave me a different feeling while walking around and seeing the sites.


Tips

As always, this trip had a lot going on in the time I was there, but I do have 3 tips for next time you are in Chicago.

  1. Make use of the Chicago public transportation. It was incredibly easy to learn how to use and is very affordable.

  2. Take time to people-watch. I love doing this on any trip, but there is always so much going on in Chicago that it's hard not to find interesting people. My favorite place to people-watch on this trip was at CloudGate and seeing their reaction to such a popular part of Chicago.

  3. This last one is from the last time I was in Chicago, but it is still true: many big cities have free, or pay-what-you-can/want, activities. This is a great way to make a trip more affordable and still have a great time.

Changes

Every trip seems to have something that doesn't go quite as planned, no matter how hard I try to plan for everything. This trip was no different.

  1. My first problem was when the carry-on rules differed between the two airlines I was using, so make sure you always check on the rules before you get to the airport to save yourself some of the craziness when it is so early in the morning.

  2. The second problem, while it turned out ok in the end, was that there are some CTA train lines that are safer than others, which I did not know when I got there. If you ever get to Chicago and take the trains, try to avoid the Red Line if possible, it's not the cleanest or nicest line there is.

Final Thoughts

Chicago 2023 is certainly a trip I won't forget and I look forward to going back again someday to take in even more that Chicago has to offer, but I'll probably wait until it's warmer to go next time.


Thanks for joining me on this adventure. Be sure to come back in the following weeks for more details about my Chicago trip.


See you next time!

Sami

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