Chicago – What You Don’t Want to Miss (Part 1)

What You Don't Want to Miss in ChicagoShould we start off with a nice pun? “When I visited Chicago, it really blew me away!” (get it…because it’s called the windy city…I thought of it myself 🙂 ) Sorry for the lame joke, but it is actually so true. (Literally, it’s like crazy windy there.) It was also tons of fun, and it really impressed me with all of the great things that it had to offer. My family and I did a lot of research on Chicago before we went back recently, and I have to say that there are certain things that you do NOT want to miss! Take a look, most of them are FREE! 🙂



  1. Take a Picture With the Bean

Bean/Cloud GateHave you ever heard of a giant mirror shaped like a bean? If so, then you might be confused about its name. Technically, it’s called Cloud Gate but I like to refer to it by its nickname, the Bean! Located on the edge of Millennial Park, even the walk can be fun as you enjoy the park’s modern art and fountains. The Bean is a classic icon of Chicago, and it’s a lot of fun to take pictures in its giant mirror. Sometimes it gets really busy during the day, but if you go at night your selfie might be a little harder to see. To get the full experience of this amazing piece of art, I recommend going during the day. Walk underneath it, take some pictures, and then keep exploring the city!

◊ Cost: FREE!

◊ Location: Millennial Park on Michigan Avenue

◊ Day/Night: Day (but do night too if you have time)


  1. Scare Yourself With a Trip to the Top of Willis Tower

Skydeck Chicago

The ledge of Skydeck Chicago, 103 stories up

The Skydeck Chicago on top of the Willis Tower is such an unforgettable experience! It’s pricey and a bit of a tourist trap, but it’s a once in a lifetime opportunity that I highly recommend. Willis Tower, formerly Sears Tower, is the second highest building in the United States. Because the skydeck is on the 103rd floor, you might get a little anxious if you’re afraid of heights. Personally, I found it thrilling! There are only a few spots where you can walk out on the ledge to snap a picture, so you might have to wait in line. The good news is that the tower offers an incredible view of the city and Lake Michigan. Enjoy the beautiful view by walking all the way around the floor, and then enjoy a laugh and a thrill as you step out onto the glass ledge!

◊ Cost: $22 (adults) $14 (children)

◊ Location: 233 S Wacker Drive

◊ Day/Night: Day

Chicago Skyline

View from the top of Willis Tower


  1. Watch the Water and Light Show at the Buckingham Fountain

Buckingham FountainGrant Park is a delightful place to take a stroll, but if you don’t have the time, then you should park your car near the Buckingham Fountain and watch one of the 20 minute water shows. Beginning at dusk, the water show is accompanied with lights and music. This makes it a great thing to do at night, especially since it doesn’t have to take up a lot of your time.

The shows begin on the hour every hour, and the last one goes off at 10:35pm. There’s some convenient parking spaces across the street from the fountain on Columbus Drive. It’s also a perfect activity to do with people of all ages! (I mean who doesn’t love a good show?)

◊ Cost: FREE!

◊ Location: in Grant Park on Columbus Drive

◊ Day/Night: Night


  1. Taste Authentic Chicago Pizza


Chicago pizza is famous. And for a good reason! It is DELICIOUS and different from anywhere else (even NYC). Having the sauce on top of my pepperoni and cheese kind of wigged me out at first, but give it a try and you (hopefully) won’t be disappointed! There are a lot of pizza places in the area; my only request is that you go somewhere that you know is definitely authentic! Giordano’s is where we went!

◊ Cost: Varies

◊ Location: Varies

◊ Day/Night: Either

Ready to plan your trip? I can help! Contact me for a FREE estimate and FREE services for a limited time! Let me be your travel agent and do the hard stuff for you!

  1. Treat Yourself to the Art Institute of Chicago


Art Institute of Chicago

A Sunday Afternoon by Georges Seurat

I love museums, whether or not other people consider them to be boring. Even if you aren’t a fan of art museums, there is SO much to appreciate at the Art Institute of Chicago! Popular artwork such as A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat, American Gothic by Grant Wood, Nighthawks by Edward Hopper, The Old Guitarist by Pablo Picasso, and The bedroom (the second one) by Vincent Van Gogh. It’s an amazing opportunity to see such famous work!

◊ Cost: $25 general admission, but discounts are given to Chicago residents, Illinois residents, students, and seniors. Children under 14 are free!

◊ Location: South Michigan Avenue

◊ Day/Night: Day (closes at 5:00pm)

These are just a few of the awesome places and activities that the Windy City has to offer. Want more? CONTINUE TO PART 2!!!

Have you ever been to Chicago before? What would say is something that you just can’t miss?

I’d love to hear your thoughts! Let me know in the comments and I’ll reply! 🙂 And join the weekly newsletter below so that you don’t miss other travel posts!

With love,


P.S. Did you read part 2??


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11 thoughts on “Chicago – What You Don’t Want to Miss (Part 1)

  1. Valarie Leonard says:

    O my goodness this is crazy but I done every single one of those and yes I would have to agree they are a must have to do for everyone while visiting Chicago!! I loved it when my husband and I went!! So much fun!!

  2. Catherine Short says:

    I’m from Chicago and you picked some great places! One thing I appreciate about the city (and I would compare it to NYC) is the typical “touristy” spots are actually worth checking out. The architecture of the city is so beautiful and I miss it often!

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