Spending Time in the Windy City

What to do in Chicago & Helpful Tips

If your trip is going to last more than a few days, I highly recommend getting the CityPass that includes admission to Shedd Aquarium, Skydeck, The Field Museum, Museum of Science & Industry or 360 Chicago Observation Deck, & Adler Planetarium or Art Institute of Chicago.  1 adult is $106 and 1 child is $86.  We didn’t get this pass, but we ended up doing a majority of the attractions included in this pass and we would have saved a lot more money if we would have bought it to begin with.


1) The Bean/Millennium Park

This is a classical must see when visiting Chicago.  An odd tourist attraction, but somehow a cool thing to do.  Stare at your reflection or take a #selfie in the Bean’s mirror like shell.  If you don’t want it to be as crowded, I recommend going at night.  We went around 10PM and it wasn’t near as crowded as when we went the following day around 2PM.  But, it’s up to you if you want to see the Bean at night or in daylight.  If you’re looking to take photos of yourself in front of the bean or of your reflection, then I recommend the daytime, but if you’re a photographer looking to get a good photo of the bean with the skyline in the background nighttime is a great time to go and eliminate the number of people in your photo.

2) Skydeck @ Willis Tower (formerly known as Sears Tower)

This was one of my favorite attractions we did here.  The skydeck is a completely glass box that hangs over the edge of the building a whopping 103 stories above Chicago.  There are 4 different boxes so more people can take photos in them at once.  We only had to wait about 10 minutes to get to the front of the line so it wasn’t too bad.  There is a professional photographer there who will take your photo, but they also allow you to take your own photos on your phone or camera.  I highly recommend if you have one, bringing a camera other than your phone camera for this because due to the lighting, it is hard to capture a good photo with your phone.

3)  Myopic Books:

This is an adorable, totally instagram worthy bookstore in downtown!  It has 3 stories so you could spend hours in there (at least I know I could).  All the books are used and organized by genre.  There are so many books to look around at so this is a great place for any book lover.  FYI, there are lots of signs saying no photos in the bookstore, but as long as you aren’t completely obvious about it, you can snap a few photos.

4)  Navy Pier:

There isn’t too much to do here exactly, but it’s a beautiful area to just walk around and take in the city.  There are some cool water exhibits inside the gardens that make for some cool photos and an area to relax for a second.  There is also a ferris wheel outside and a boat ride you can take along the water.  Unfortunately, since it was way too cold outside we didn’t do either of those, but it warmer weather I bet those attractions are a blast.

5)  Chicago Fire Firestation:

1360 S. Blue Island Ave

If you have ever seen even just one episode of the show Chicago Fire, this is a pretty cool place to visit.  Firehouse 51 is a currently operating firehouse in the Chicago department that also doubles as the set for some of the scenes of the famous tv show, Chicago Fire.  All of the outside scenes and scenes with the firetrucks are shot here while the rest of the scenes are shot in their studios on set.  The place I was staying was pretty close to the firestation so I decided to take my morning run over there and check it out.  As I ran up, I saw lots of people outside the firestation and big cameras.  “NO WAY!  This is not happening,” was the thoughts running through my mind at that moment.  But it was true!  They were filming an episode of Chicago Fire that very day!  I guess I decided to visit on the right day!  Despite the below freezing weather, I stood outside for about an hour watching them film and even got to see and take a photo from afar of 2 of my favorite actors from the show: Jesse Spencer (who plays Matthew Casey) & Monica Raymund (who plays Gabriela Dawson).  Jesse was walking to his van and he waved at me.  I almost died right there.  Sadly, I did not get a photo with them, but it was still such a cool experience!!  If they are not filming when you visit, the firefighters of house 51 will let you come inside and let you walk around inside.  There is even a little Chicago Fire museum so I heard.  So if you’re a fan of the show, this is a must see!

6)  Museum of Contemporary Art

This is a small art museum in Chicago with a couple floors of really beautiful artwork.  Since it’s not too big, you really don’t need to plan to spend more than a few hours here.  The admission is by donations, but there is a recommended minimum amount, but if you can’t pay that, they will let you into the museum with whatever money you do have to pay.


1) Brunch ( yes, this place is literally called brunch)

We stumbled upon this place while trying to find a coffee shop we saw online and this place ended up being 10x better than the coffee shop.  As the name implies, they serve breakfast food and it was delicious!!  They have some pretty insane menu items so we all ordered something different and then shared it all.  We ordered the donut bites, strawberry stuffed french toast, & smores french toast.  I give this place 5 stars!!!  The service was excellent, too.

2) Lou Malnati’s Pizzeria (DEEP DISH PIZZA!!)

I had always heard of the famous Chicago deep dish pizza and was pretty pumped to try some on this trip.  My reaction?  It’s interesting.  It is definitely different from normal pizza!  Basically, it is not the same as normal pizza because it is almost like a pie with very thick crust, followed by cheese on the bottom, and sauce on the top.  So everything is opposite.  It was pretty yummy and a must do in Chicago just to say you have, but I think personally I prefer to stick with classic pizza.  What can I say?  I guess I like to stick to classics.

3)  Sweet Mandy B’s

As the name hints at, this is a dessert shop for all the sweet tooth’s out there.  Sweet Mandy B’s has all types of homemade desserts from cupcakes to cookies to cakes to more!  They have it all.  They even have gluten free options.  The place is pretty aesthetic, too which makes for even more instagram worthy shots!  (Can you tell I like instagram?)  10/10 recommend this place for a tasty treat after that deep dish pizza or any other meal.

Welp, that’s all I’ve got for today.  Those were my highlights of visiting the windy city.  I hope you enjoyed reading about my adventures and that these tips help you plan you trip to Chicago!

Texan On The Go

2 thoughts on “Spending Time in the Windy City

  1. Great blog and very good information for future travelers. Love reading about your adventures. You didn’t post any dates however, so a little lost in time.

    Liked by 1 person

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