Whirlwind in the Windy City

It's Wednesday and I'm just now getting around to sharing my weekend. Bad blogger, I know. I didn't get to a computer for longer than 15 minutes until Tuesday night, so hopefully you'll forgive me, just this once? I think the reason why I'm getting to my weekend a few days late might make up for it: I spent the weekend in Chicago!

I finally got the guts to kick my fear of flying to the curb at least long enough for my first trip to the Windy City. Although Ben and I have talked about going to Chicago for a couple years now, more so in the last couple months, we didn't actually plan this trip until 2 weeks beforehand. And by "plan" I mean we booked a flight and a hotel, but had absolutely zero ideas about what we'd do and see once we got there. That's kind of our travel style.

I'm not going to write a full recap of everything we ate, did, and saw because frankly I think those posts are boring and I like you guys too much to do that to you. Instead, here are some photos and some of our Chicago adventures.

I was honestly a little underwhelmed upon arrival (sorry, Chicagoans, please don't hate me). Chicago didn't strike me the same as my beloved NYC and Boston, which I'm actually pretty thankful for because now I don't have another city to add to my Want-To-Move-To List. Whew.


The Signature Lounge on the 96th floor of the John Hancock Building was a fun way to get a view of the city (as good of a view as we were going to get anyway - this was the least cloudy it was the whole time we were there). We didn't do the Willis Tower but I think this was a good alternative. It was pricy, but at least or $50 got us drinks and an appetizer to go along with our view.


Deep dish pizza was on the dinner menu both nights we were there.



I wasn't that impressed by Lake Michigan. But then I found the river, and it was super cool.


The Chicago Architecture Foundation boat tour was definitely worth it! I felt so happy that I have a good vocabulary and a background in Classics, art history, AND civil engineering because with all of that, I totally understood everything our docent said (and she said a lot)!

Our City Running Tour was awesome! Even thought it was cloudy and foggy and rainy and a little cold. I think running is the absolute best and most fun way to see a city and I love that this company exists (full review to come)!

Any recent or upcoming travels? What's your favorite city?

20 comments :

  1. I need to know more about this City Running Tour stuff. Sounds excellent! I wish I'd known about it when I was all alone in Nashville last winter, confined to the hotel gym treadmill. Glad you got your Chicago trip in and enjoyed. Happy Thanksgiving!

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  2. I've never heard of a city running tour! Sounds interesting. I'm trying not to hold it against you that you didn't like my favorite place in the whole world. Looks like it was kind of foggy and wet and probably cold, so maybe you need to go back in the spring or something :)

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  3. Good for you! My friend has a fear of flying and I can definitely appreciate how hard it is to get on a plane when you have a fear of flying. I loved Chicago but didn't really expect to, but the food and the museums and all the cool statues, loved them!

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    1. Thanks, girl! The flight was only about 2 hours, so it was manageable. There was definitely a lot of cool stuff to see!

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  4. That pizza looks yummy and Chicago is on my lists of cities to see! Such a great trip girl!

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  5. i started reading this and instantly was like WHAT! she didn't love Chicago?! and then i thought about the reasons why I love it and couldn't really think of any. besides food. RPM goes down as one of the better meals of my 25 years. I think it is just my undying love for the midwest that made me feel like you were crazy.. but i am meh about chicago. i think i need to find the places where locals go instead of the super touristy parts of the city and i would have a totally different experience. i will say their public transportation is really amazing so that's a plus. :) (and i know you won't think i am a total weirdo for talking about a city's public transportation)

    my dad has serious flight anxiety and i always feel so terrible for him when we are all so excited about a vacation while he is so nervous. my dad and i have done some LONG HAUL flights together-japan and argentina - and we still laugh about the flights and how horrible they were. the flight from argentina played the movie hairspray.. continuously. it was an overnight like 12 hour flight. it was awful. they then played the song bubbly for landing.. continuously. makes for good laughs now but while we were up there, he was not a pleased man. back to you! way to go flying! i can't wait to fly in a few months to come hang out with you!

    are you expecting a lot of snow over the long weekend? i heard some parts out there are getting some MN style snow storms. :)

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  6. I just started to like you a whole lot more! I'm also underwhelmed by Chicago. As a native Minneapolis-ite, I just feel like it's a little bit larger version of Minneapolis. Ho-humm. The lake is dirty and it's cold and windy (why the wind?! WHY??) But the food in that city is amazing! Deep dish is where it's at.

    Now that you're flying, may I recommend New Orleans or Charleston? Those cities are amazing, fun, and have GREAT food!

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    1. These comments are so funny to me, I had no idea Chicago was so polarizing! I've never been to Minneapolis though so I can't compare. I thought I would like the lake - being from the beach, I'm used to having a large body of water nearby, so I thought that the lake would make it not feel so land-locked? So we stayed right on it and, I don't know, it just didn't do anything for me. The river was cool though!

      Girrrllllll I am Charleston born and bred! You're not kidding about the food. I ran my first marathon there earlier this year and the post-race food there was grits. GRITS! Amazing. I haven't been to New Orleans but would like to!

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  7. It is always interesting to see different peoples views on different cities. I have never been to Chicago so I don't really know how I feel about it. I like visiting other cities, but try to go with zero expectations so as not to end up underwhelmed like you described. The running tour sounds really cool and like a great way to learn a new city!

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  8. I think travel weekend recaps deserve a few extra days :) I love reading travel recap posts and try to keep mine as non boring as possible but normally I just want to share alllll the things, so its hard.
    I have been to Chicago once, it was ok but I had a bad experience there, so I wanted to go back and we were supposed to go for our anniversary and didn't :(
    I can't believe you booked something 2 weeks out, that's giving my plan all the things in advance self heart palpitations.
    I love the city running tour idea, I was thinking about doing one in NYC but I don't know the areas and I'm a bit scared lol. Also KC can't run, womp womp. I'm considering it though!

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  9. Chicago has been on our list for awhile, but now that we're out east, I don't think it's going to happen any time soon. There are so many places on the east coast we want to explore first. We did a trip to Boston in the spring and absolutely loved it! We're definitely planning a trip back there soon and it's awesome that we can drive there. Of course New York is number one on the list! Neither of us have been there so we're definitely saving our pennies for that! Great pictures and that deep dish pizza...YUM!!

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    1. New York and Boston are my favorites! We fell in love with Boston from the first second we got there. Like, seriously, the week after we got back from our trip my husband had a job offer there (unfortunately we decided it just wasn't the right time for us) soooo...yeah, we loved it, haha! I like NYC a little more than Boston. There's just no place like it! That's where I want to move when I finish school.

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  10. I've never been to Chicago - thinking it may be a 2015 visit. I really do love San Francisco, Seattle, and Vancover (west coast theme here hehe). The deep dish looks good!

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    1. We want to do a West Coast trip next and those 3 would be the highlights, for sure! As much as I am an East Coast girl I think I'll really like the West Coast.

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  11. I loved Chicago a lot, sorry it was just okay for you! It was one of my favorite cities to visit aside from San Francisco.

    I've been to Boston a billion times, two of my best friends lived there so I've been regularly for the last 15 years. I really like that town too. Another BFF has lived in NYC for 15 years and I'm always very happy to come home from there.

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  12. I went to Chicago for my marathon, but I really want to go back just to do the tourist thing.
    I'd love to do a running tour of a city. My hubby doesn't run though. I'll often wake up on the first morning of a trip and go out for a few miles on my own to get my barings. It is often one of my favorite moments of a trip.

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    1. How did you like running the marathon there? I thought about that constantly while we were there.
      Running on vacation is one of my absolute favorite things! My husband doesn't really run either, and he hates running in the rain, so I was really grateful that he joined me!

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    2. How did you like running the marathon there? I thought about that constantly while we were there.
      Running on vacation is one of my absolute favorite things! My husband doesn't really run either, and he hates running in the rain, so I was really grateful that he joined me!

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  13. You have to go to the Michigan side of Lake Michigan-- a million times better :) You got some great shots of the city-- I haven't been to Chicago in forever (my husband has never been) but if we ever visit I definitely want to do one of the architecture tours.

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  14. I think Chicago is more fun in the warmer weather. But I enjoyed going downtown in May this year for a wedding!! I definitely enjoy doing the running thing to see a city :) glad you had a good time!

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