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Chicago: Exploring the Windy City

January 24, 2020

Chicago. Chi-Town. The windy city. Home of deep dish pizza, towering skyscrapers, and the infamous silver Bean (which I learned was actually first called Cloud Gate). I flew up to Chicago over spring break last March to meet up with some family, and had a fantastic time. I already can’t wait to go back and scope out some of the more local places, but here is a list of some of my favorite things we did that I would highly recommend as a first-time tourist (including a GREAT photo-op of the skyline, taken at a very interesting spot). Also, pretty much all of these activities are family-friendly as well!

Hero Coffee

We started off our first day downtown by getting off the train and heading towards Millennium Park. On our way there we stumbled upon this inconspicuous little coffee shop hidden down an alley (I later learned that this narrow cobblestone street is known as Pickwick Alley, which was giving off strong Harry-Potter-Diagon-Alley-vibes.) I had actually seen pictures of this cute coffee shop with the light up “coffee” sign before, but because they had multiple locations I wasn’t sure where this one was located. Make sure to check out my Google Map of Chicago at the end of this post if you want to see where this one is!

Millennium Park

Millennium park was only a few blocks down from the coffee shop; it’s a pretty cool park but the highlight was definitely the huge silver bean sitting in the middle of everything. The amount of mirror selfies we took on it is actually embarrassing. (Also if you want to stand out in Chicago, in a sea of navy and black clothing, wear a white top and maroon plaid pants – you’ll be sure to turn a few heads)

Magnificent Mile

We had some time to kill before lunch, so we walked around an area called the “Magnificent Mile” which is known for it’s shopping. I love all the historic architecture in downtown cities, and I had especially wanted to see the Chicago Theater, with the huge neon sign and letter-board in such fun colors!


After killing some time walking around downtown, we walked over to Giordiano’s for a Chicago-staple meal: deep dish pizza. Needless to say, it did not disappoint, and I was full after just one piece. (A sign of a good meal – no photos because it was devoured before anyone could whip out their phone)

Garfield Park Conservatory

Another highlight of the trip was Garfield Park Conservatory – a MASSIVE conservatory filled with basically every type of plant imaginable. This is also a great activity if you’re visiting Chicago in the winter; it’s a great escape from the frigid weather into a bubble of warm, tropical paradise.

One of the best parts about the conservatory? It’s FREE ADMISSION (they do accept donations at the door) and it’s open 365 days a year from 9:00 am – 5:00 pm, and on Wednesdays until 8:00 pm!

I LOVE plants, so I was in heaven! Also was really excited to find this Moroccan-style water fountain – so many beautiful things around every corner of this place!

Bombo Bar

If you’re looking for a sweet treat, you can’t go wrong with Bombo Bar; they have some extravagant hot chocolates (I mean, look at those toppings!) and their flavor-infused donuts are delicious.

Signature Lounge

Next up: An EPIC view from the John Hancock Building! Now, here’s the secret: instead of getting the $25 observation deck tickets, you can actually go up to the Signature Lounge for free! The catch? You have to buy a *pricey* cocktail BUT it’s still less than the observation deck ticket AND you get a cocktail! A win-win in my book.

And as for the interesting location with a breathtaking view of the city? (Seen above, right) It’s actually in the women’s restroom of the Signature Lounge! (Sorry boys) As weird as it might be to take photos in a bathroom, I promise these views are so good that you definitely will not be the only one!

More Activities!

Although not pictured, we also visited the Museum of Science and Industry, as well as the Shedd Aquarium. They were SO fun, and great activities for all ages. If I get the chance to go back in warmer weather, I definitely want to check out their Architecture Boat Tour! Don’t forget to check out below the Google Map I created with all of these mentioned locations tagged in it.

Until next time Chicago!


  • Sheila Isom

    January 24, 2020 at 8:38 pm

    Love it Carly, you did a fantastic job. Can’t wait to read more of your adventures!

    1. Carly

      January 25, 2020 at 4:53 am

      Thanks Sheila! It was such a fun trip!!

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