Chicago Trip: I Need a Take Two

There aren’t too many things in life I enjoy more than traveling & spending time with my family, so it’s no surprise that one of the trips I look forward to every year is our annual family travel weekend built around my dad (and now brother’s) work convention. I’ve been going since I was really young, and they host them in different places every year. This year it was in Chicago, which was…well, underwhelming, to be honest. Bummer.

I so wanted to love Chicago as I’ve heard it’s a great city, and I’m sure it’s much different if you live there and get to explore it fully and find “your places,” but to visit for 4 days at the end of April just didn’t work for me the way I would have liked. I need another trip to the Windy City to improve my impression.

Let me start with the positives: I got to spend a weekend away with my family, which is always invaluable and outstanding and all sorts of wonderful, regardless of location.

My brother and I look more alike to me in this photo than in any we’ve ever taken, I think!


Love these two. Especially when they dress alike. 🙂

And our hotel, the Palmer House (Hilton), was lovely. I would absolutely recommend it if you’re planning a visit to Chicago. The lobby is beautiful and impressive, the staff is friendly (except for the lobby bartender, who was awful), the gym is impressive for a hotel, the beds and rooms are comfy, and it’s in a central location right by Millennium Park and the art museum. Great choice of a hotel.

photos taken from their website:


Millennium Park was pretty (although I’m sure it’s much nicer on a not-gray-and-freezing day), and I did get my obligatory “bean” photos, so that was a success:



I also had some great quality time with my mom, shopping & at the park and seeing the Van Gogh exhibit Bedrooms at the Art Institute of Chicago, which we both really enjoyed and which made me realize I want to be more intentional about going to museums and other cultural events. It was interesting and thought-provoking.

Other highlights included getting to spend time with one of my closest high school friends (with whom I was wayyyyy overdue for a visit and who has a gorgeous condo there), going salsa dancing on Saturday night with my brother, and and buying new Paige jeans that I realllllly like.

The negatives: well, I guess they all basically tie back to one main thing: the weather. It was awful. Absolutely atrociously terrible — rainy, windy and in the 40s the entire time — and prevented us from wanting to do much of anything. We didn’t walk around and explore, we didn’t take the boat architecture tour, we didn’t have any rooftop or patio or really any restaurant experiences at all —

and the #1 bummer for me was that I didn’t get to run the Lakefront Trail along Lake Michigan, which I was realllllly looking forward to doing. I didn’t see Navy Pier or experience any lovely Chicago Spring weather at all, as there wasn’t one single day that begged for us to be outdoors. I did run every day, but only on the treadmill. It was quite depressing, actually, and that’s what I hope to change next time I visit this city! The weather really can make or break your experience with a place, and unfortunately it tainted my first taste of Chicago.

So, til next time, Chi-town. Hope you treat me with a sunnier disposition then.

Ever gone on a vacation where it rained the whole time?
Been to Chicago? What did you like/dislike most?
Fave brand of jeans?


15 thoughts on “Chicago Trip: I Need a Take Two

  1. You definitely need to go back. I suggest the Chicago Marathon 😉 I love Michigan Ave and the Lakefront Trail. So bummed you missed out running on it!!! As for the jeans, I always love my reliable Luckys, but I have a pair of Diesels that I really love too.

    • I know, I really want to go back and visit my friend in the summer. So bummed about it. Maybe the marathon one year — but it’s the same wknd as the one I run upstate, so hasn’t been on my radar!

  2. Man, what a bummer. The one thing I LOVE about Chicago is spring and summer. When the weather cooperates, it is an absolutely beautiful and clean city. Lake Michigan is amazing. But I can totally understand how the weather would ruin it for you. I hate when spring weather goes in that direction. That gym, by the way, is amazing!

  3. I am so sorry that you came the weekend that you did. The weather was indeed beyond terrible! There is so much about Chicago that I think you would love, but I will also say that Chicago has a very different energy from New York–I think you are just more of a NYC girl than a Chicago girl, but I think that you would also really enjoy Chicago (and all the fun restaurants!) if you had the chance. Plus, I’m here. But it is very different from NYC.

    • I know, it was a bummer – and bummer that we didn’t get a chance to meet either! Hopefully both of those things will be rectified upon my return. I can see how Chicago has a lot to offer and I look forward to exploring it more, even if I am a true NYC gal at heart. 🙂

    • Everyone seems to love it! I’ll have to go back for sure. I basically just stayed in my one area and didn’t get to explore as much as I’d have liked.

  4. That hotel looks amazing! I’ve never been to Chicago, but it’s something that I’m looking forward to. It sucks that the weather was a bummer, but unfortunately it’s not something we can control. I’m sure once you get to run around the lake Michigan, your opinion will change drastically lol! I’ve never been on a vacation where it rained all the time, but once I got super sick and it did affect my perception of that city. So I totally get you. But then, yay to quality family time!

    How Running Makes Us Happy, But Happiness Makes Us Better Runners:

    • So true about not being able to control the weather, although I wish that wasn’t the case! 🙂 Gah being sick on vaca must be the worst. Hope you enjoy Chicago when you get there!

  5. What a bummer that the weather sucked.

    I’ve only been there to a conference and it was before I was running. i definitely want to go back.

  6. The weather can make or break a vacation. At least you are honest about the experience. Most people would probably only highlight the positives and leave it at that. I’ve actually been to Chicago once and wasn’t a fan – mostly because of that darn wind! Even on a sunny day, the wind can make everything so cold. I’m not a fan of wind. Now, let’s talk about that hotel gym –> WOW! I’ve never seen a gym like that. Not a bad place to run at all. 🙂

    • The gym was so great! They had yoga and class studios and a spa and everything as well, and the locker rooms were amazinggggg. I’m not into wind either, but def want to return to Chicago and pray for sunshine. 🙂

  7. I loved spending time with you in Chicago. I love spending time with you anywhere. The pictures are great! I hope your next trip to Chicago will be a better one.

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