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must do things in Chicago (+ what I wish I would have done!)

Writer's picture: TannaTanna

Chilling on SkyDeck

So this one is a throwback. I traveled to Chicago in the fall of 2017, but I didn't have a blog then! I've been obsessed with Chicago since I visited, and it was too good of a trip not to share.


Before going to Chicago, I had only been on a plane once in my life. So at the age of 23, when my boyfriend and I were given the opportunity by one of our best friends (shout out HMWalker) for BOGO free plane tickets, we jumped on it.


The only things I knew about Chicago until my trip were negative things, so I was a little skeptical about it. DON'T BELIEVE THE NEGATIVES!! Except that it's super cold in the winter. Don't go in the winter. We went in early fall and it was so beautiful, and the temperature was in the 70's the whole time. I fell in love with the city so hard!


Goddess and the Baker. Terrible acai bowls, beautiful decor.

Here are some of the best things to do if you want to visit Chicago, especially for the first time!


1) SkyDeck Chicago


Definitely one of the most "Instagrammable" moments on the list! Go to the top of Willis Tower, step out onto a glass ledge, and get an awesome view of the city! Go early- it gets crowded as the day goes on. The tower was also a location of filming in Ferris Beuller's Day off! Info here: https://theskydeck.com/


SkyDeck Chicago
Seriously such a cool experience.


2) 360 Chicago


Located in the John Hancock building, get the best ever view of the city from up here! Plus, they have a bar at the top. If you're really brave, this place has something similar to SkyDeck called "Tilt" where they lean you out over the edge of the building within a glass box. Info here: https://360chicago.com/


360 Chicago
Lake Michigan and Lake Shore Drive from 360 Chicago

Chicago Sunset
It gets super crowded at sunset for this reason!

3) Deep Dish Pizza


This one is a no-brainer! My fave was from Giordano's (a chain with many locations!) Just don't wait until you're already hangry to go, because you'll be waiting a minute for that pizza to bake. I WANT SOME RIGHT NOW.


Lou Malnati's Deep Dish Pizza
This pizza was actually from Lou Malnati's, another super popular chain. But I prefer Giordano's!

4) Millennium Park and the Art Institute of Chicago


Millennium park is where you can see the famous Cloud Gate, or, "The Bean." I again recommend going early before anyone is there to crowd it, since the statue is SUPER reflective and you won't be able to get a great photo otherwise (see: below). Tip: Go to Cindy's rooftop bar nearby at any time of day to get a great view of the park!



If you're into art, go to the Art Institute right next door. See famous paintings like Liz by Andy Warhol, American Gothic by Grant Wood, and A Sunday on La Grande Jatte by Georges Seurat.


Liz by Andy Warhol
Admiring Liz- I've always been a fan of Andy Warhol's work!

6) Michigan Avenue


The "touristy" area of downtown, this is where all the shopping is at, and it is beautiful and lively. There are statues of painted K9 police dogs lining the streets and pretty decorations. Go, whether you want to shop or not! And get some Garrett Chicago style popcorn, you will not be disappointed.


See the Garrett's bag? That's the best popcorn you will ever have.

7) See a Cubs game at Wrigley Field


Such a historic field, it's a can't miss! We went to the very last game of the Cubs season and saw the 2016 World Series Trophy. The whole surrounding area of Wrigleyville is hopping before and after games, and there are endless bars and restaurants to hang at!



View of Wrigleyville and the Chicago skyline from the stadium.

My very own Cubs dad hat!

8) Lincoln Park Zoo


This zoo is FREE and it is so beautiful! You can see a gorgeous silhouette of the city from here. The Garfield Park Conservatory is nearby, which is also free and gorgeous!



Transported to Jurassic World inside the Garfield Park Conservatory.

Some things I wish I had gotten to do:


Hotel recommendation:


Kimpton Hotel Allegro. The hotel is art deco and beautifully decorated. I fell in love with it online and had to stay there. It was great!



If you made it to the end of this, congrats and THANK YOU! We just did so much in Chicago and all of it was awesome so it's hard to keep this one brief! If you have any questions about the city, I'd love to hear them and answer them!


Do you guys have any travel plans for this year?? I'm trying to go back to San Francisco, go to Colorado, and to Seattle or Portland. I'd love to hear what trips you have planned!


♡,tanna

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