He Can’t Move to Chicago, It’s Too Dangerous!

Senior pictures in Austin TX at the Graffiti Park

My son was a senior in high school and announced to us that he wanted to attend college in Chicago. Yes, that Chicago! The one with one of the highest murder rates in the country. That was my first thought. My second thought was how would the boy who wears beanies and heavy jackets when the Texas winter drops below 60 degrees, survive a Chicago winter?

My solution…Merry Christmas family…we are all going to Chicago for vacation in JANUARY! To my surprise, what I found is a city with the most amazing food, culture, and people and one that I will return to again and again!

Chicago in Winter

Chicago Transit System

One of the most amazing things about Chicago is its transit system. We flew in, grabbed an Uber from the Airport to our AMAZING Airbnb (you should stay there too!) where Jessica let us leave our luggage (not always an option but good to ask). And that was it! No rental car, no looking for parking…we got a transit pass and went everywhere.

First thing, download a transit app! It guided us every step of the way, telling us what mode of transportation to take from point A to point B. We felt safe and secure the whole time (of course with a 6′ 5″ husband I tend to feel safe and secure a lot)

After all the amazingness that is Chicago, we took another Uber back to the airport. I definitely recommend using the Chicago transit system and leaving the rental cars at the airport!

Chicago “L” train

The Food

It’s hard to decide what was better the food or the sights…so I’ll just give you the highlights of both! I don’t think we had a bad meal in Chicago, but two things that they Do. So. Well. are pizza and donuts!! We couldn’t possible try all the pizza or donut places in Chicago, but of the one’s we tried I have our favorites.

Lou Malnati’s Pizzeria

For delivery and all around great pizza, Lou Malnati’s Pizzeria is the BEST!!! I consider myself a pizza aficionado (in my own head) and Lou’s was up among the best I’ve had. We got both a deep dish and a thin crust and both were so incredible. I will say that I am definitely team Thin Crust, but Lou made me consider the other side.

Lou Malnati’s in Lincoln Park
Lou Malnati’s pizza

Giordano’s Pizza

Now, if you are looking for authentic Chicago style deep dish pizza and you find yourself downtown then Giordano’s is your place. There are not enough words for all of that gooey, cheesy, pepperoni-ey goodness, but I assure you that you will not be disappointed.

Giordano’s Deep Dish


Finally, donuts, what can I say, I love donuts. One morning hubby and I got up from our apartment and walked to the closest donut shop and found an amazing little shop called Firecakes Donuts. I’m just sayin… it was sooo worth the walk! My favorite was the Pistachio Old Fashioned, but all were amazing!

Another donut shop that you can find all over town is Stan’s. O-M-G you have to get the Blueberry Fritter. Whenever someone tells me they are going to Chicago, my first thought is “Blueberry Fritter!!!” You must get one…can I please get an Amen in the comments below!

Stan’s Donuts…Blueberry Fritters!

Free Sights in Chicago

The food is amazing but the sight are equally amazing. There are so many things to do in Chicago. Especially so many FREE things to do in Chicago! Some of our favorites were the Lincoln Park Zoo (our AirBnb was right across the street). We were there for Christmas time so it was especially beautiful with all of the Christmas lights. I think it’s one of the only free admission zoos that I know of. Do you know of any others?

Gorilla at the Lincoln Park Zoo
Lion at the Lincoln Park Zoo

And everyone has to go to the Bean. There is no better photo op than the Bean. It brings out the crazy in the most reserved of people!

Hilarity at The Bean
Family photo op at The Bean

So Much To Do

Some of our other favorites were Shedd Aquarium, Grant Park Ice Skating Ribbon, Navy Pier…with that marvelous ferris wheel, Willis Tower with the glass skydeck, and the unforgettable Art Institute of Chicago. I have to be honest, on the last one I thought it might be a little boring, but it was remarkable. From Andy Warhol to Picasso, you are inches away from works of art that you have only seen in books. It was breathtaking!

Shedd Aquarium
Grant Park Ice Ribbon
Navy Pier Ferris Wheel Shenanigans
Have to get a kiss at the top of the Ferris Wheel at Navy Pier!
Willis Tower Skydeck…will you or won’t you?
Willis Tower Skydeck
I literally scooted out into the box…so scary 🙂
Andy Warhol at Chicago Art Institute
Just a little Picasso…Chicago Art Institute
Monet…Chicago Art Institute
Chicago Art Institute with the Chicago skyline

Chicago was a stunning surprise that I cannot wait to return to. Do you have any places that took you by surprise? I would love to hear about them! Join me on Instagram, Facebook, or Pinterest! 

  1. Esther

    November 27th, 2019 at 3:16 am

    …..makes me want to visit…and spend some time there

  2. Jana Beckett

    November 27th, 2019 at 7:41 pm

    You definitely should! There are so many things to do…I can’t wait to go back! Blueberry Fritters are waiting 🙂

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