72 Hours in Chicago (Part I)

We finally made it to Chicago! Lucky for us we had a wedding to go to which finally got our butts moving to the Midwest.

I’ve always wanted to head to the Windy City, it’s been on the bucket list, so I took my handy travel notebook from owlcrate and went exploring. Before I dive into the highlights here’s some things to keep in mine in relation to transportation. The “L” is so simple and affordable. A 3-day train pass is only $20.00, I think on the first day we got our money back. You can also use the Metro (though only if you’re leaving the city) and Uber or Lyft if you really can’t get someplace any other way (we ran into this when we were leaving the Cubs baseball game).

Okay! Now on to where to eat, what to see and where to go!


Where to Eat

Like any city, Chicago is known for its food (especially it’s pizza) and while we had some dish deep pizza, it wasn’t my favorite. But there were SO many other places that were delicious and I’d recommend to anyone. One of those being Big Star. 20170831_130347

The tacos were SO good, and you could get a pitcher of Margaritas to share at the table as well. Not only were the tacos delicious but the atmosphere was pretty awesome too. Basically you got one of the above tacos an order, you could mix and match what you wanted and then it was delivered family style. It was different, but delicious — if/when we go back, I wouldn’t be angry if we went there again. Big Star isn’t expensive either, it was $30 a person but only because we got Margaritas. You could easily go there for cheaper without the alcohol.

Our favorite quick breakfast place ended up being Stan’s Donuts. The inside felt retro and sleek and the donuts were legitimate donuts. Probably the best I’ve ever had for sure. There are so many options too, ones with fruit in them, some with nutella or peanut butter — something for anyone which makes it even better. A breakfast here is an easy $6.50 and totally worth it. Other places we went included Public House Chicago, Portillos, Kanela’s (seen below), and Lou’s Pizza House. The foodies in us loved them all. For drinks, check out Tapster if you have time. It’s basically a tasting room but you get to walk up and just taste whatever you want. It’s also really affordable, we had a lot of fun here.


The Attractions

If you’re planning to really explore, I would recommend the Go City Card (more on that in two days). There are so many places to see in Chicago that you could probably spend an entire week there (hello to all the museums).

Our first stop was to the Bean in Millenium Park, one of the staples of Chicago, after which we walked to the Buckingham Fountain which not only provided a lovely park but awesome views of the city from all sides and angles. It wasn’t on the list (or maybe it was?) but my boyfriend surprised us with the little detour. It’s really close to the Bean so it’s not out of the way in any means.

Other attractions we saw were the ones that really got my blood moving — I’m afraid of heights but I still managed to do both 360 Chicago and Skydeck Chicago. I wanted to like the Skydeck better because of the actually ledge (shown below) but it was so crowded it was kind of a let down. 360 Chicago offers some of the same views, plus a bar and the tilt (for $7 extra) which includes you tilting OVER the building (no thank you), I’ll stick to the ledge. On the left is a view from 360 Chicago, while on the right is me freaking out sitting on the ledge of the Chicago Skydeck.

But my favorite thing was the architecture tour. One of things stunning about Chicago and what makes it so different from other cities I’ve been to is that there is a river going right through it. One that people can kayak on or take a boat through that really goes through the heart of the skyscrapers. Of all the things we did, this is the one I would tell everyone to make time to do.


If you have time, which I think you would, go see the Chicago sign, a staple of the city that everyone knows, and if you’re lucky like us, you might be able to check out a Chicago Cubs game. Very Fenway-esque, you feel like you’re walking back in time to the good old days.

Other things I’d like to do next time:

  • The Planetarium
  • Science and Industry Museum
  • Rent some bikes and bike around the waterfront/beaches

Have you guys been to Chicago? What did I miss? I’m heading there for about a day in half in October so advice is welcome!

8 thoughts on “72 Hours in Chicago (Part I)

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